Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Frontier Airlines

The cheapest airline(s) flying from Orlando to Chicago is Frontier Airlines.

  • Frontier Airlines Frontier Airlines
  • Spirit Airlines Spirit Airlines
  • United Airlines United Airlines
  • American Airlines American Airlines
  • Southwest Airlines Southwest Airlines
  • Sun Country Airlines Sun Country Airlines
  • JetBlue Airways JetBlue Airways
  • Alaska Airlines Alaska Airlines
Cheapest Month January

Travel Period: December 2024 - November 2025

The cheapest month(s) to fly from Orlando to Chicago is January.

  • Dec 2024
  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
Cheapest Day of the Week Tuesday

The cheapest day(s) of the week to fly from Orlando to Chicago is Tuesday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday

Flight Schedules

Last Updated: Sat, 2 Nov, 2024

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    • Airline Filter by Airline
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      • Availability
        • M
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        • S
      • 19:05 MCO
        20:55 MDW
        2Hrs, 50m Direct
      • MCOOrlando International Airport 19:05 - MDW 20:55 2h 50m Direct
      • MCOOrlando International Airport 19:05
      • MDWChicago Midway Airport 20:55
      • 2h 50m
      • Direct
      • Southwest Airlines (WN 2711)Boeing 737 800
      • Southwest Airlines (WN 2711)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 800
      • 19:35 MCO
        21:25 MDW
        2Hrs, 50m Direct
      • MCOOrlando International Airport 19:35 - MDW 21:25 2h 50m Direct
      • MCOOrlando International Airport 19:35
      • MDWChicago Midway Airport 21:25
      • 2h 50m
      • Direct
      • Southwest Airlines (WN 979)Boeing 737 700
      • Southwest Airlines (WN 979)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 20:25 MCO
        22:35 ORD
        3Hrs, 10m Direct
      • MCOOrlando International Airport 20:25 - ORD 22:35 3h 10m Direct
      • MCOOrlando International Airport 20:25
      • ORDChicago O'Hare International Airport 22:35
      • 3h 10m
      • Direct
      • Southwest Airlines (WN 4243)Boeing 737 700
      • Southwest Airlines (WN 4243)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 20:35 MCO
        22:25 MDW
        2Hrs, 50m Direct
      • MCOOrlando International Airport 20:35 - MDW 22:25 2h 50m Direct
      • MCOOrlando International Airport 20:35
      • MDWChicago Midway Airport 22:25
      • 2h 50m
      • Direct
      • Southwest Airlines (WN 2836)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2836)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 22:05 MCO
        23:50 MDW
        2Hrs, 45m Direct
      • MCOOrlando International Airport 22:05 - MDW 23:50 2h 45m Direct
      • MCOOrlando International Airport 22:05
      • MDWChicago Midway Airport 23:50
      • 2h 45m
      • Direct
      • Southwest Airlines (WN 2836)Boeing 737 700
      • Southwest Airlines (WN 2836)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 700
      • 06:00 MCO
        07:55 MDW
        2Hrs, 55m Direct
      • MCOOrlando International Airport 06:00 - MDW 07:55 2h 55m Direct
      • MCOOrlando International Airport 06:00
      • MDWChicago Midway Airport 07:55
      • 2h 55m
      • Direct
      • Frontier Airlines (F9 3853)Airbus A320 Neo
      • Frontier Airlines (F9 3853)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Airbus A320 Neo
      • 06:10 MCO
        08:05 MDW
        2Hrs, 55m Direct
      • MCOOrlando International Airport 06:10 - MDW 08:05 2h 55m Direct
      • MCOOrlando International Airport 06:10
      • MDWChicago Midway Airport 08:05
      • 2h 55m
      • Direct
      • Frontier Airlines (F9 3853)Airbus A320 Neo
      • Frontier Airlines (F9 3853)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Airbus A320 Neo
      • 06:10 MCO
        08:05 MDW
        2Hrs, 55m Direct
      • MCOOrlando International Airport 06:10 - MDW 08:05 2h 55m Direct
      • MCOOrlando International Airport 06:10
      • MDWChicago Midway Airport 08:05
      • 2h 55m
      • Direct
      • Frontier Airlines (F9 1457)Airbus A320 Neo
      • Frontier Airlines (F9 1457)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Airbus A320 Neo
      • 06:15 MCO
        08:10 MDW
        2Hrs, 55m Direct
      • MCOOrlando International Airport 06:15 - MDW 08:10 2h 55m Direct
      • MCOOrlando International Airport 06:15
      • MDWChicago Midway Airport 08:10
      • 2h 55m
      • Direct
      • Frontier Airlines (F9 3853)Airbus A320 Neo
      • Frontier Airlines (F9 3853)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Airbus A320 Neo
      • 06:35 MCO
        08:30 MDW
        2Hrs, 55m Direct
      • MCOOrlando International Airport 06:35 - MDW 08:30 2h 55m Direct
      • MCOOrlando International Airport 06:35
      • MDWChicago Midway Airport 08:30
      • 2h 55m
      • Direct
      • Southwest Airlines (WN 858)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 858)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 07:00 MCO
        09:13 ORD
        3Hrs, 13m Direct
      • MCOOrlando International Airport 07:00 - ORD 09:13 3h 13m Direct
      • MCOOrlando International Airport 07:00
      • ORDChicago O'Hare International Airport 09:13
      • 3h 13m
      • Direct
      • American Airlines (AA 598)Boeing 737 800
      • American Airlines (AA 598)
        • M
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        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 07:10 MCO
        09:05 MDW
        2Hrs, 55m Direct
      • MCOOrlando International Airport 07:10 - MDW 09:05 2h 55m Direct
      • MCOOrlando International Airport 07:10
      • MDWChicago Midway Airport 09:05
      • 2h 55m
      • Direct
      • Southwest Airlines (WN 898)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 898)
        • -
        • T
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        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 07:30 MCO
        09:33 ORD
        3Hrs, 03m Direct
      • MCOOrlando International Airport 07:30 - ORD 09:33 3h 03m Direct
      • MCOOrlando International Airport 07:30
      • ORDChicago O'Hare International Airport 09:33
      • 3h 03m
      • Direct
      • United Airlines (UA 2673)Boeing 737 Max 9 Passenger
      • United Airlines (UA 2673)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 Max 9 Passenger
      • 07:50 MCO
        12:05 MDW
        5Hrs, 15m Direct
      • MCOOrlando International Airport 07:50 - MDW 12:05 5h 15m Direct
      • MCOOrlando International Airport 07:50
      • MDWChicago Midway Airport 12:05
      • 5h 15m
      • Direct
      • Southwest Airlines (WN 1740)Boeing 737 700
      • Southwest Airlines (WN 1740)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 07:52 MCO
        10:00 ORD
        3Hrs, 08m Direct
      • MCOOrlando International Airport 07:52 - ORD 10:00 3h 08m Direct
      • MCOOrlando International Airport 07:52
      • ORDChicago O'Hare International Airport 10:00
      • 3h 08m
      • Direct
      • Frontier Airlines (F9 3043)Airbus A321 Neo
      • Frontier Airlines (F9 3043)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Airbus A321 Neo
      • 07:55 MCO
        10:06 ORD
        3Hrs, 11m Direct
      • MCOOrlando International Airport 07:55 - ORD 10:06 3h 11m Direct
      • MCOOrlando International Airport 07:55
      • ORDChicago O'Hare International Airport 10:06
      • 3h 11m
      • Direct
      • American Airlines (AA 1557)Boeing 737 800
      • American Airlines (AA 1557)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 07:55 MCO
        09:45 MDW
        2Hrs, 50m Direct
      • MCOOrlando International Airport 07:55 - MDW 09:45 2h 50m Direct
      • MCOOrlando International Airport 07:55
      • MDWChicago Midway Airport 09:45
      • 2h 50m
      • Direct
      • Southwest Airlines (WN 898)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 898)
        • M
        • -
        • -
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        • F
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 08:00 MCO
        10:17 ORD
        3Hrs, 17m Direct
      • MCOOrlando International Airport 08:00 - ORD 10:17 3h 17m Direct
      • MCOOrlando International Airport 08:00
      • ORDChicago O'Hare International Airport 10:17
      • 3h 17m
      • Direct
      • American Airlines (AA 1135)Boeing 737 800
      • American Airlines (AA 1135)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 800
      • 08:05 SFB
        09:52 RFD
        2Hrs, 47m Direct
      • SFBOrlando Sanford International Airport 08:05 - RFD 09:52 2h 47m Direct
      • SFBOrlando Sanford International Airport 08:05
      • RFDChicago Rockford Airport 09:52
      • 2h 47m
      • Direct
      • Allegiant Air LLC (G4 1344)Airbus
      • Allegiant Air LLC (G4 1344)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Airbus
      • 08:05 SFB
        09:52 RFD
        2Hrs, 47m Direct
      • SFBOrlando Sanford International Airport 08:05 - RFD 09:52 2h 47m Direct
      • SFBOrlando Sanford International Airport 08:05
      • RFDChicago Rockford Airport 09:52
      • 2h 47m
      • Direct
      • Allegiant Air LLC (G4 2970)Airbus
      • Allegiant Air LLC (G4 2970)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Airbus
      • 08:40 MCO
        10:45 ORD
        3Hrs, 05m Direct
      • MCOOrlando International Airport 08:40 - ORD 10:45 3h 05m Direct
      • MCOOrlando International Airport 08:40
      • ORDChicago O'Hare International Airport 10:45
      • 3h 05m
      • Direct
      • Southwest Airlines (WN 4080)Boeing 737 700
      • Southwest Airlines (WN 4080)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 08:50 MCO
        10:56 ORD
        3Hrs, 06m Direct
      • MCOOrlando International Airport 08:50 - ORD 10:56 3h 06m Direct
      • MCOOrlando International Airport 08:50
      • ORDChicago O'Hare International Airport 10:56
      • 3h 06m
      • Direct
      • Spirit Airlines (NK 1842)Airbus A320 Neo
      • Spirit Airlines (NK 1842)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Airbus A320 Neo
      • 08:50 MCO
        10:40 MDW
        2Hrs, 50m Direct
      • MCOOrlando International Airport 08:50 - MDW 10:40 2h 50m Direct
      • MCOOrlando International Airport 08:50
      • MDWChicago Midway Airport 10:40
      • 2h 50m
      • Direct
      • Southwest Airlines (WN 3478)Boeing 737 800
      • Southwest Airlines (WN 3478)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 800
      • 09:00 MCO
        12:50 MDW
        4Hrs, 50m Direct
      • MCOOrlando International Airport 09:00 - MDW 12:50 4h 50m Direct
      • MCOOrlando International Airport 09:00
      • MDWChicago Midway Airport 12:50
      • 4h 50m
      • Direct
      • Southwest Airlines (WN 3094)Boeing 737 700
      • Southwest Airlines (WN 3094)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 09:10 MCO
        13:00 MDW
        4Hrs, 50m Direct
      • MCOOrlando International Airport 09:10 - MDW 13:00 4h 50m Direct
      • MCOOrlando International Airport 09:10
      • MDWChicago Midway Airport 13:00
      • 4h 50m
      • Direct
      • Southwest Airlines (WN 1650)Boeing 737 700
      • Southwest Airlines (WN 1650)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 700
      • 09:25 MCO
        11:15 MDW
        2Hrs, 50m Direct
      • MCOOrlando International Airport 09:25 - MDW 11:15 2h 50m Direct
      • MCOOrlando International Airport 09:25
      • MDWChicago Midway Airport 11:15
      • 2h 50m
      • Direct
      • Southwest Airlines (WN 546)Boeing 737 700
      • Southwest Airlines (WN 546)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 09:30 MCO
        11:33 ORD
        3Hrs, 03m Direct
      • MCOOrlando International Airport 09:30 - ORD 11:33 3h 03m Direct
      • MCOOrlando International Airport 09:30
      • ORDChicago O'Hare International Airport 11:33
      • 3h 03m
      • Direct
      • United Airlines (UA 395)Airbus A321 Neo
      • United Airlines (UA 395)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Airbus A321 Neo
      • 09:56 MCO
        12:05 ORD
        3Hrs, 09m Direct
      • MCOOrlando International Airport 09:56 - ORD 12:05 3h 09m Direct
      • MCOOrlando International Airport 09:56
      • ORDChicago O'Hare International Airport 12:05
      • 3h 09m
      • Direct
      • Frontier Airlines (F9 3043)Airbus A321 Neo
      • Frontier Airlines (F9 3043)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Airbus A321 Neo
      • 10:00 MCO
        14:25 MDW
        5Hrs, 25m Direct
      • MCOOrlando International Airport 10:00 - MDW 14:25 5h 25m Direct
      • MCOOrlando International Airport 10:00
      • MDWChicago Midway Airport 14:25
      • 5h 25m
      • Direct
      • Southwest Airlines (WN 3890)Boeing 737 800
      • Southwest Airlines (WN 3890)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 800
      • 10:25 MCO
        12:15 MDW
        2Hrs, 50m Direct
      • MCOOrlando International Airport 10:25 - MDW 12:15 2h 50m Direct
      • MCOOrlando International Airport 10:25
      • MDWChicago Midway Airport 12:15
      • 2h 50m
      • Direct
      • Southwest Airlines (WN 546)Boeing 737 800
      • Southwest Airlines (WN 546)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 10:30 MCO
        12:33 ORD
        3Hrs, 03m Direct
      • MCOOrlando International Airport 10:30 - ORD 12:33 3h 03m Direct
      • MCOOrlando International Airport 10:30
      • ORDChicago O'Hare International Airport 12:33
      • 3h 03m
      • Direct
      • United Airlines (UA 1485)Boeing 737 Max 9 Passenger
      • United Airlines (UA 1485)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • Boeing 737 Max 9 Passenger
      • 11:05 MCO
        13:08 ORD
        3Hrs, 03m Direct
      • MCOOrlando International Airport 11:05 - ORD 13:08 3h 03m Direct
      • MCOOrlando International Airport 11:05
      • ORDChicago O'Hare International Airport 13:08
      • 3h 03m
      • Direct
      • United Airlines (UA 1485)Boeing 737 Max 9 Passenger
      • United Airlines (UA 1485)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 9 Passenger
      • 11:05 MCO
        13:00 MDW
        2Hrs, 55m Direct
      • MCOOrlando International Airport 11:05 - MDW 13:00 2h 55m Direct
      • MCOOrlando International Airport 11:05
      • MDWChicago Midway Airport 13:00
      • 2h 55m
      • Direct
      • Southwest Airlines (WN 3764)Boeing 737 800
      • Southwest Airlines (WN 3764)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 11:17 MCO
        13:27 ORD
        3Hrs, 10m Direct
      • MCOOrlando International Airport 11:17 - ORD 13:27 3h 10m Direct
      • MCOOrlando International Airport 11:17
      • ORDChicago O'Hare International Airport 13:27
      • 3h 10m
      • Direct
      • Frontier Airlines (F9 3043)Airbus A321 Neo
      • Frontier Airlines (F9 3043)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Airbus A321 Neo
      • 11:45 MCO
        13:40 MDW
        2Hrs, 55m Direct
      • MCOOrlando International Airport 11:45 - MDW 13:40 2h 55m Direct
      • MCOOrlando International Airport 11:45
      • MDWChicago Midway Airport 13:40
      • 2h 55m
      • Direct
      • Southwest Airlines (WN 546)Boeing 737 800
      • Southwest Airlines (WN 546)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 800
      • 11:52 MCO
        13:46 MDW
        2Hrs, 54m Direct
      • MCOOrlando International Airport 11:52 - MDW 13:46 2h 54m Direct
      • MCOOrlando International Airport 11:52
      • MDWChicago Midway Airport 13:46
      • 2h 54m
      • Direct
      • Frontier Airlines (F9 1457)Airbus A320 Neo
      • Frontier Airlines (F9 1457)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Airbus A320 Neo
      • 12:15 MCO
        14:25 ORD
        3Hrs, 10m Direct
      • MCOOrlando International Airport 12:15 - ORD 14:25 3h 10m Direct
      • MCOOrlando International Airport 12:15
      • ORDChicago O'Hare International Airport 14:25
      • 3h 10m
      • Direct
      • Southwest Airlines (WN 350)Boeing 737 800
      • Southwest Airlines (WN 350)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 12:30 MCO
        14:32 ORD
        3Hrs, 02m Direct
      • MCOOrlando International Airport 12:30 - ORD 14:32 3h 02m Direct
      • MCOOrlando International Airport 12:30
      • ORDChicago O'Hare International Airport 14:32
      • 3h 02m
      • Direct
      • United Airlines (UA 2475)Boeing 757 300 Series
      • United Airlines (UA 2475)
        • M
        • T
        • -
        • T
        • F
        • -
        • -
      • Boeing 757 300 Series
      • 12:30 MCO
        14:33 ORD
        3Hrs, 03m Direct
      • MCOOrlando International Airport 12:30 - ORD 14:33 3h 03m Direct
      • MCOOrlando International Airport 12:30
      • ORDChicago O'Hare International Airport 14:33
      • 3h 03m
      • Direct
      • United Airlines (UA 2475)Airbus A321 Neo
      • United Airlines (UA 2475)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • Airbus A321 Neo
      • 12:30 MCO
        14:33 ORD
        3Hrs, 03m Direct
      • MCOOrlando International Airport 12:30 - ORD 14:33 3h 03m Direct
      • MCOOrlando International Airport 12:30
      • ORDChicago O'Hare International Airport 14:33
      • 3h 03m
      • Direct
      • United Airlines (UA 2475)Boeing 737 900
      • United Airlines (UA 2475)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 900
      • 12:40 MCO
        14:30 MDW
        2Hrs, 50m Direct
      • MCOOrlando International Airport 12:40 - MDW 14:30 2h 50m Direct
      • MCOOrlando International Airport 12:40
      • MDWChicago Midway Airport 14:30
      • 2h 50m
      • Direct
      • Southwest Airlines (WN 4265)Boeing 737 800
      • Southwest Airlines (WN 4265)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 12:58 MCO
        14:59 ORD
        3Hrs, 01m Direct
      • MCOOrlando International Airport 12:58 - ORD 14:59 3h 01m Direct
      • MCOOrlando International Airport 12:58
      • ORDChicago O'Hare International Airport 14:59
      • 3h 01m
      • Direct
      • American Airlines (AA 985)Airbus
      • American Airlines (AA 985)
        • M
        • T
        • -
        • T
        • F
        • S
        • S
      • Airbus
      • 12:58 MCO
        15:03 ORD
        3Hrs, 05m Direct
      • MCOOrlando International Airport 12:58 - ORD 15:03 3h 05m Direct
      • MCOOrlando International Airport 12:58
      • ORDChicago O'Hare International Airport 15:03
      • 3h 05m
      • Direct
      • American Airlines (AA 985)Boeing 737 800
      • American Airlines (AA 985)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 13:15 MCO
        15:05 MDW
        2Hrs, 50m Direct
      • MCOOrlando International Airport 13:15 - MDW 15:05 2h 50m Direct
      • MCOOrlando International Airport 13:15
      • MDWChicago Midway Airport 15:05
      • 2h 50m
      • Direct
      • Southwest Airlines (WN 5113)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 5113)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 13:55 MCO
        18:10 MDW
        5Hrs, 15m Direct
      • MCOOrlando International Airport 13:55 - MDW 18:10 5h 15m Direct
      • MCOOrlando International Airport 13:55
      • MDWChicago Midway Airport 18:10
      • 5h 15m
      • Direct
      • Southwest Airlines (WN 1462)Boeing 737 700
      • Southwest Airlines (WN 1462)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 15:30 MCO
        19:50 MDW
        5Hrs, 20m Direct
      • MCOOrlando International Airport 15:30 - MDW 19:50 5h 20m Direct
      • MCOOrlando International Airport 15:30
      • MDWChicago Midway Airport 19:50
      • 5h 20m
      • Direct
      • Southwest Airlines (WN 1462)Boeing 737 800
      • Southwest Airlines (WN 1462)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 15:35 MCO
        17:25 MDW
        2Hrs, 50m Direct
      • MCOOrlando International Airport 15:35 - MDW 17:25 2h 50m Direct
      • MCOOrlando International Airport 15:35
      • MDWChicago Midway Airport 17:25
      • 2h 50m
      • Direct
      • Southwest Airlines (WN 2962)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2962)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 15:35 MCO
        17:39 ORD
        3Hrs, 04m Direct
      • MCOOrlando International Airport 15:35 - ORD 17:39 3h 04m Direct
      • MCOOrlando International Airport 15:35
      • ORDChicago O'Hare International Airport 17:39
      • 3h 04m
      • Direct
      • American Airlines (AA 3267)Boeing 737 800
      • American Airlines (AA 3267)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 800
      • 15:40 MCO
        17:30 MDW
        2Hrs, 50m Direct
      • MCOOrlando International Airport 15:40 - MDW 17:30 2h 50m Direct
      • MCOOrlando International Airport 15:40
      • MDWChicago Midway Airport 17:30
      • 2h 50m
      • Direct
      • Southwest Airlines (WN 1523)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1523)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 15:46 MCO
        17:52 ORD
        3Hrs, 06m Direct
      • MCOOrlando International Airport 15:46 - ORD 17:52 3h 06m Direct
      • MCOOrlando International Airport 15:46
      • ORDChicago O'Hare International Airport 17:52
      • 3h 06m
      • Direct
      • American Airlines (AA 3267)Boeing 737 800
      • American Airlines (AA 3267)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 800
      • 15:50 MCO
        18:55 MDW
        4Hrs, 05m Direct
      • MCOOrlando International Airport 15:50 - MDW 18:55 4h 05m Direct
      • MCOOrlando International Airport 15:50
      • MDWChicago Midway Airport 18:55
      • 4h 05m
      • Direct
      • Southwest Airlines (WN 3655)Boeing 737 700
      • Southwest Airlines (WN 3655)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 16:10 MCO
        18:26 ORD
        3Hrs, 16m Direct
      • MCOOrlando International Airport 16:10 - ORD 18:26 3h 16m Direct
      • MCOOrlando International Airport 16:10
      • ORDChicago O'Hare International Airport 18:26
      • 3h 16m
      • Direct
      • Frontier Airlines (F9 2041)Airbus A321 Neo
      • Frontier Airlines (F9 2041)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Airbus A321 Neo
      • 16:15 MCO
        18:17 ORD
        3Hrs, 02m Direct
      • MCOOrlando International Airport 16:15 - ORD 18:17 3h 02m Direct
      • MCOOrlando International Airport 16:15
      • ORDChicago O'Hare International Airport 18:17
      • 3h 02m
      • Direct
      • United Airlines (UA 1828)Boeing 777
      • United Airlines (UA 1828)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 777
      • 16:30 MCO
        18:20 MDW
        2Hrs, 50m Direct
      • MCOOrlando International Airport 16:30 - MDW 18:20 2h 50m Direct
      • MCOOrlando International Airport 16:30
      • MDWChicago Midway Airport 18:20
      • 2h 50m
      • Direct
      • Southwest Airlines (WN 1844)Boeing 737 800
      • Southwest Airlines (WN 1844)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 16:39 MCO
        18:55 ORD
        3Hrs, 16m Direct
      • MCOOrlando International Airport 16:39 - ORD 18:55 3h 16m Direct
      • MCOOrlando International Airport 16:39
      • ORDChicago O'Hare International Airport 18:55
      • 3h 16m
      • Direct
      • Frontier Airlines (F9 2041)Airbus A320 Neo
      • Frontier Airlines (F9 2041)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Airbus A320 Neo
      • 16:55 MCO
        19:00 ORD
        3Hrs, 05m Direct
      • MCOOrlando International Airport 16:55 - ORD 19:00 3h 05m Direct
      • MCOOrlando International Airport 16:55
      • ORDChicago O'Hare International Airport 19:00
      • 3h 05m
      • Direct
      • American Airlines (AA 1247)Boeing 737 800
      • American Airlines (AA 1247)
        • -
        • T
        • W
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 17:00 MCO
        18:50 MDW
        2Hrs, 50m Direct
      • MCOOrlando International Airport 17:00 - MDW 18:50 2h 50m Direct
      • MCOOrlando International Airport 17:00
      • MDWChicago Midway Airport 18:50
      • 2h 50m
      • Direct
      • Southwest Airlines (WN 2401)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2401)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 17:01 MCO
        19:16 ORD
        3Hrs, 15m Direct
      • MCOOrlando International Airport 17:01 - ORD 19:16 3h 15m Direct
      • MCOOrlando International Airport 17:01
      • ORDChicago O'Hare International Airport 19:16
      • 3h 15m
      • Direct
      • Frontier Airlines (F9 2041)Airbus A320 Neo
      • Frontier Airlines (F9 2041)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Airbus A320 Neo
      • 17:16 MCO
        19:31 ORD
        3Hrs, 15m Direct
      • MCOOrlando International Airport 17:16 - ORD 19:31 3h 15m Direct
      • MCOOrlando International Airport 17:16
      • ORDChicago O'Hare International Airport 19:31
      • 3h 15m
      • Direct
      • Frontier Airlines (F9 2041)Airbus A320 Neo
      • Frontier Airlines (F9 2041)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Airbus A320 Neo
      • 17:28 MCO
        19:24 MDW
        2Hrs, 56m Direct
      • MCOOrlando International Airport 17:28 - MDW 19:24 2h 56m Direct
      • MCOOrlando International Airport 17:28
      • MDWChicago Midway Airport 19:24
      • 2h 56m
      • Direct
      • Frontier Airlines (F9 1457)Airbus A320 Neo
      • Frontier Airlines (F9 1457)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Airbus A320 Neo
      • 17:39 MCO
        19:44 ORD
        3Hrs, 05m Direct
      • MCOOrlando International Airport 17:39 - ORD 19:44 3h 05m Direct
      • MCOOrlando International Airport 17:39
      • ORDChicago O'Hare International Airport 19:44
      • 3h 05m
      • Direct
      • American Airlines (AA 1247)Boeing 737 800
      • American Airlines (AA 1247)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 17:40 MCO
        19:45 ORD
        3Hrs, 05m Direct
      • MCOOrlando International Airport 17:40 - ORD 19:45 3h 05m Direct
      • MCOOrlando International Airport 17:40
      • ORDChicago O'Hare International Airport 19:45
      • 3h 05m
      • Direct
      • American Airlines (AA 1247)Boeing 737 800
      • American Airlines (AA 1247)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 800
      • 17:40 MCO
        19:30 MDW
        2Hrs, 50m Direct
      • MCOOrlando International Airport 17:40 - MDW 19:30 2h 50m Direct
      • MCOOrlando International Airport 17:40
      • MDWChicago Midway Airport 19:30
      • 2h 50m
      • Direct
      • Southwest Airlines (WN 2401)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2401)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 17:45 MCO
        21:55 MDW
        5Hrs, 10m Direct
      • MCOOrlando International Airport 17:45 - MDW 21:55 5h 10m Direct
      • MCOOrlando International Airport 17:45
      • MDWChicago Midway Airport 21:55
      • 5h 10m
      • Direct
      • Southwest Airlines (WN 534)Boeing 737 700
      • Southwest Airlines (WN 534)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 18:05 MCO
        20:15 ORD
        3Hrs, 10m Direct
      • MCOOrlando International Airport 18:05 - ORD 20:15 3h 10m Direct
      • MCOOrlando International Airport 18:05
      • ORDChicago O'Hare International Airport 20:15
      • 3h 10m
      • Direct
      • Spirit Airlines (NK 1147)Airbus A320 Neo
      • Spirit Airlines (NK 1147)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Airbus A320 Neo
      • 18:10 MCO
        20:13 ORD
        3Hrs, 03m Direct
      • MCOOrlando International Airport 18:10 - ORD 20:13 3h 03m Direct
      • MCOOrlando International Airport 18:10
      • ORDChicago O'Hare International Airport 20:13
      • 3h 03m
      • Direct
      • United Airlines (UA 2000)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2000)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 18:10 MCO
        20:13 ORD
        3Hrs, 03m Direct
      • MCOOrlando International Airport 18:10 - ORD 20:13 3h 03m Direct
      • MCOOrlando International Airport 18:10
      • ORDChicago O'Hare International Airport 20:13
      • 3h 03m
      • Direct
      • United Airlines (UA 2000)Boeing 737 900
      • United Airlines (UA 2000)
        • M
        • -
        • -
        • T
        • -
        • S
        • S
      • Boeing 737 900
      • 18:20 MCO
        20:10 MDW
        2Hrs, 50m Direct
      • MCOOrlando International Airport 18:20 - MDW 20:10 2h 50m Direct
      • MCOOrlando International Airport 18:20
      • MDWChicago Midway Airport 20:10
      • 2h 50m
      • Direct
      • Southwest Airlines (WN 1340)Boeing 737 700
      • Southwest Airlines (WN 1340)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 19:05 MCO
        01:00 MDW
        6Hrs, 55m 1 Stop (HOU)
      • MCOOrlando International Airport 19:05 - MDW 01:00 6h 55m 1 Stop (HOU) Houston
      • MCOOrlando International Airport 19:05
        HOUHouston Hobby Airport 22:40
      • HOUHouston Hobby Airport 20:50
        MDWChicago Midway Airport 01:00
      • 6h 55m (1h 50m)
      • 1 Stop HOU · Houston 1h 50m
      • Southwest Airlines (WN 5555)Boeing 737 700
        Southwest Airlines (WN 1732)Boeing 737 700
      • Southwest Airlines (WN 5555)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 19:05 MCO
        23:05 MDW
        5Hrs, 00m 1 Stop (STL)
      • MCOOrlando International Airport 19:05 - MDW 23:05 5h 1 Stop (STL) Saint Louis
      • MCOOrlando International Airport 19:05
        STLSt Louis Lambert Intl Airport 21:55
      • STLSt Louis Lambert Intl Airport 20:45
        MDWChicago Midway Airport 23:05
      • 5h (1h 10m)
      • 1 Stop STL · Saint Louis 1h 10m
      • Southwest Airlines (WN 2825)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 652)Boeing 737 800
      • Southwest Airlines (WN 2825)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 19:09 MCO
        23:59 ORD
        5Hrs, 50m 1 Stop (IAH)
      • MCOOrlando International Airport 19:09 - ORD 23:59 5h 50m 1 Stop (IAH) Houston
      • MCOOrlando International Airport 19:09
        IAHHouston George Bush Intercontinental Airport 21:30
      • IAHHouston George Bush Intercontinental Airport 20:50
        ORDChicago O'Hare International Airport 23:59
      • 5h 50m (40m)
      • 1 Stop IAH · Houston 40m
      • United Airlines (UA 1630)Boeing 737 900
        United Airlines (UA 556)Boeing 737 Max 8 Passenger
      • United Airlines (UA 1630)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 19:09 MCO
        23:59 ORD
        5Hrs, 50m 1 Stop (IAH)
      • MCOOrlando International Airport 19:09 - ORD 23:59 5h 50m 1 Stop (IAH) Houston
      • MCOOrlando International Airport 19:09
        IAHHouston George Bush Intercontinental Airport 21:30
      • IAHHouston George Bush Intercontinental Airport 20:50
        ORDChicago O'Hare International Airport 23:59
      • 5h 50m (40m)
      • 1 Stop IAH · Houston 40m
      • United Airlines (UA 1630)Boeing 737 900
        United Airlines (UA 556)Boeing 737 900
      • United Airlines (UA 1630)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 19:13 MCO
        23:20 ORD
        5Hrs, 07m 1 Stop (IAD)
      • MCOOrlando International Airport 19:13 - ORD 23:20 5h 07m 1 Stop (IAD) Washington
      • MCOOrlando International Airport 19:13
        IADWashington Dulles International Airport 22:16
      • IADWashington Dulles International Airport 21:23
        ORDChicago O'Hare International Airport 23:20
      • 5h 07m (53m)
      • 1 Stop IAD · Washington 53m
      • United Airlines (UA 1997)Boeing 737 900
        United Airlines (UA 1738)Boeing 737 800
      • United Airlines (UA 1997)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 19:15 MCO
        23:58 MDW
        5Hrs, 43m 1 Stop (ATL)
      • MCOOrlando International Airport 19:15 - MDW 23:58 5h 43m 1 Stop (ATL) Atlanta
      • MCOOrlando International Airport 19:15
        ATLAtlanta Hartsfield-Jackson Intl Airport 23:00
      • ATLAtlanta Hartsfield-Jackson Intl Airport 21:05
        MDWChicago Midway Airport 23:58
      • 5h 43m (1h 55m)
      • 1 Stop ATL · Atlanta 1h 55m
      • Frontier Airlines (F9 3975)Airbus
        Frontier Airlines (F9 2291)Airbus A320 Neo
      • Frontier Airlines (F9 3975)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 19:15 MCO
        23:10 MDW
        4Hrs, 55m 1 Stop (FLL)
      • MCOOrlando International Airport 19:15 - MDW 23:10 4h 55m 1 Stop (FLL) Miami
      • MCOOrlando International Airport 19:15
        FLLFort Lauderdale/Hollywood Intl Airport 21:00
      • FLLFort Lauderdale/Hollywood Intl Airport 20:20
        MDWChicago Midway Airport 23:10
      • 4h 55m (40m)
      • 1 Stop FLL · Miami 40m
      • Southwest Airlines (WN 4665)Boeing 737 700
        Southwest Airlines (WN 2037)Boeing 737 700
      • Southwest Airlines (WN 4665)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 19:15 MCO
        23:20 ORD
        5Hrs, 05m 1 Stop (IAD)
      • MCOOrlando International Airport 19:15 - ORD 23:20 5h 05m 1 Stop (IAD) Washington
      • MCOOrlando International Airport 19:15
        IADWashington Dulles International Airport 22:16
      • IADWashington Dulles International Airport 21:25
        ORDChicago O'Hare International Airport 23:20
      • 5h 05m (51m)
      • 1 Stop IAD · Washington 51m
      • United Airlines (UA 1997)Boeing 737 900
        United Airlines (UA 1738)Boeing 737 800
      • United Airlines (UA 1997)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 19:15 MCO
        23:20 ORD
        5Hrs, 05m 1 Stop (IAD)
      • MCOOrlando International Airport 19:15 - ORD 23:20 5h 05m 1 Stop (IAD) Washington
      • MCOOrlando International Airport 19:15
        IADWashington Dulles International Airport 22:16
      • IADWashington Dulles International Airport 21:25
        ORDChicago O'Hare International Airport 23:20
      • 5h 05m (51m)
      • 1 Stop IAD · Washington 51m
      • United Airlines (UA 1997)Boeing 737 900
        United Airlines (UA 1738)Boeing 737 700
      • United Airlines (UA 1997)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 19:15 MCO
        23:20 ORD
        5Hrs, 05m 1 Stop (IAD)
      • MCOOrlando International Airport 19:15 - ORD 23:20 5h 05m 1 Stop (IAD) Washington
      • MCOOrlando International Airport 19:15
        IADWashington Dulles International Airport 22:16
      • IADWashington Dulles International Airport 21:25
        ORDChicago O'Hare International Airport 23:20
      • 5h 05m (51m)
      • 1 Stop IAD · Washington 51m
      • United Airlines (UA 1997)Boeing 737 900
        United Airlines (UA 1738)Airbus
      • United Airlines (UA 1997)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 19:15 MCO
        23:20 ORD
        5Hrs, 05m 1 Stop (IAD)
      • MCOOrlando International Airport 19:15 - ORD 23:20 5h 05m 1 Stop (IAD) Washington
      • MCOOrlando International Airport 19:15
        IADWashington Dulles International Airport 22:16
      • IADWashington Dulles International Airport 21:25
        ORDChicago O'Hare International Airport 23:20
      • 5h 05m (51m)
      • 1 Stop IAD · Washington 51m
      • United Airlines (UA 1997)Boeing 737 900
        United Airlines (UA 1738)Boeing 737 900
      • United Airlines (UA 1997)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 19:20 MCO
        23:08 MDW
        4Hrs, 48m 1 Stop (ATL)
      • MCOOrlando International Airport 19:20 - MDW 23:08 4h 48m 1 Stop (ATL) Atlanta
      • MCOOrlando International Airport 19:20
        ATLAtlanta Hartsfield-Jackson Intl Airport 22:11
      • ATLAtlanta Hartsfield-Jackson Intl Airport 21:10
        MDWChicago Midway Airport 23:08
      • 4h 48m (1h 01m)
      • 1 Stop ATL · Atlanta 1h 01m
      • Frontier Airlines (F9 3975)Airbus
        Frontier Airlines (F9 2779)Airbus A320 Neo
      • Frontier Airlines (F9 3975)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 19:20 MCO
        23:59 ORD
        5Hrs, 39m 1 Stop (ATL)
      • MCOOrlando International Airport 19:20 - ORD 23:59 5h 39m 1 Stop (ATL) Atlanta
      • MCOOrlando International Airport 19:20
        ATLAtlanta Hartsfield-Jackson Intl Airport 22:51
      • ATLAtlanta Hartsfield-Jackson Intl Airport 21:10
        ORDChicago O'Hare International Airport 23:59
      • 5h 39m (1h 41m)
      • 1 Stop ATL · Atlanta 1h 41m
      • Frontier Airlines (F9 3975)Airbus
        Frontier Airlines (F9 3397)Airbus A320 Neo
      • Frontier Airlines (F9 3975)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 19:25 MCO
        00:43 ORD
        6Hrs, 18m 1 Stop (IAH)
      • MCOOrlando International Airport 19:25 - ORD 00:43 6h 18m 1 Stop (IAH) Houston
      • MCOOrlando International Airport 19:25
        IAHHouston George Bush Intercontinental Airport 22:04
      • IAHHouston George Bush Intercontinental Airport 21:09
        ORDChicago O'Hare International Airport 00:43
      • 6h 18m (55m)
      • 1 Stop IAH · Houston 55m
      • Spirit Airlines (NK 961)Airbus Industrie A320 Sharklets
        Spirit Airlines (NK 962)Airbus Industrie A320 Sharklets
      • Spirit Airlines (NK 961)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 19:29 MCO
        01:15 MDW
        6Hrs, 46m 1 Stop (DFW)
      • MCOOrlando International Airport 19:29 - MDW 01:15 6h 46m 1 Stop (DFW) Dallas
      • MCOOrlando International Airport 19:29
        DFWDallas/Fort Worth Intl Airport 22:59
      • DFWDallas/Fort Worth Intl Airport 21:41
        MDWChicago Midway Airport 01:15
      • 6h 46m (1h 18m)
      • 1 Stop DFW · Dallas 1h 18m
      • Frontier Airlines (F9 1951)Airbus A320 Neo
        Frontier Airlines (F9 2882)Airbus A320 Neo
      • Frontier Airlines (F9 1951)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 19:40 MCO
        00:16 ORD
        5Hrs, 36m 1 Stop (CLT)
      • MCOOrlando International Airport 19:40 - ORD 00:16 5h 36m 1 Stop (CLT) Charlotte
      • MCOOrlando International Airport 19:40
        CLTCharlotte Airport 22:56
      • CLTCharlotte Airport 21:32
        ORDChicago O'Hare International Airport 00:16
      • 5h 36m (1h 24m)
      • 1 Stop CLT · Charlotte 1h 24m
      • American Airlines (AA 2502)Airbus
        American Airlines (AA 1180)Boeing 737 800
      • American Airlines (AA 2502)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 19:50 MCO
        00:50 MDW
        6Hrs, 00m 1 Stop (DAL)
      • MCOOrlando International Airport 19:50 - MDW 00:50 6h 1 Stop (DAL) Dallas
      • MCOOrlando International Airport 19:50
        DALDallas/Fort Worth Love Field Airport 22:45
      • DALDallas/Fort Worth Love Field Airport 21:45
        MDWChicago Midway Airport 00:50
      • 6h (1h)
      • 1 Stop DAL · Dallas 1h
      • Southwest Airlines (WN 2049)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 5269)Boeing 737 700
      • Southwest Airlines (WN 2049)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 19:50 MCO
        23:10 MDW
        4Hrs, 20m 1 Stop (ATL)
      • MCOOrlando International Airport 19:50 - MDW 23:10 4h 20m 1 Stop (ATL) Atlanta
      • MCOOrlando International Airport 19:50
        ATLAtlanta Hartsfield-Jackson Intl Airport 22:15
      • ATLAtlanta Hartsfield-Jackson Intl Airport 21:25
        MDWChicago Midway Airport 23:10
      • 4h 20m (50m)
      • 1 Stop ATL · Atlanta 50m
      • Southwest Airlines (WN 3193)Boeing 737 700
        Southwest Airlines (WN 4703)Boeing 737 800
      • Southwest Airlines (WN 3193)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 20:00 MCO
        23:55 MDW
        4Hrs, 55m 1 Stop (ATL)
      • MCOOrlando International Airport 20:00 - MDW 23:55 4h 55m 1 Stop (ATL) Atlanta
      • MCOOrlando International Airport 20:00
        ATLAtlanta Hartsfield-Jackson Intl Airport 22:58
      • ATLAtlanta Hartsfield-Jackson Intl Airport 21:54
        MDWChicago Midway Airport 23:55
      • 4h 55m (1h 04m)
      • 1 Stop ATL · Atlanta 1h 04m
      • Frontier Airlines (F9 3975)Airbus
        Frontier Airlines (F9 2779)Airbus A320 Neo
      • Frontier Airlines (F9 3975)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 20:05 MCO
        01:00 MDW
        5Hrs, 55m 1 Stop (HOU)
      • MCOOrlando International Airport 20:05 - MDW 01:00 5h 55m 1 Stop (HOU) Houston
      • MCOOrlando International Airport 20:05
        HOUHouston Hobby Airport 22:40
      • HOUHouston Hobby Airport 21:45
        MDWChicago Midway Airport 01:00
      • 5h 55m (55m)
      • 1 Stop HOU · Houston 55m
      • Southwest Airlines (WN 4305)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1732)Boeing 737 700
      • Southwest Airlines (WN 4305)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 20:20 MCO
        23:55 MDW
        4Hrs, 35m 1 Stop (STL)
      • MCOOrlando International Airport 20:20 - MDW 23:55 4h 35m 1 Stop (STL) Saint Louis
      • MCOOrlando International Airport 20:20
        STLSt Louis Lambert Intl Airport 22:45
      • STLSt Louis Lambert Intl Airport 22:00
        MDWChicago Midway Airport 23:55
      • 4h 35m (45m)
      • 1 Stop STL · Saint Louis 45m
      • Southwest Airlines (WN 2825)Boeing 737 800
        Southwest Airlines (WN 652)Boeing 737 700
      • Southwest Airlines (WN 2825)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:00 MCO
        08:42 ORD
        4Hrs, 42m 1 Stop (CLT)
      • MCOOrlando International Airport 05:00 - ORD 08:42 4h 42m 1 Stop (CLT) Charlotte
      • MCOOrlando International Airport 05:00
        CLTCharlotte Airport 07:34
      • CLTCharlotte Airport 06:48
        ORDChicago O'Hare International Airport 08:42
      • 4h 42m (46m)
      • 1 Stop CLT · Charlotte 46m
      • American Airlines (AA 1896)Airbus
        American Airlines (AA 2843)Airbus
      • American Airlines (AA 1896)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 05:00 MCO
        10:48 ORD
        6Hrs, 48m 1 Stop (CLT)
      • MCOOrlando International Airport 05:00 - ORD 10:48 6h 48m 1 Stop (CLT) Charlotte
      • MCOOrlando International Airport 05:00
        CLTCharlotte Airport 09:33
      • CLTCharlotte Airport 06:48
        ORDChicago O'Hare International Airport 10:48
      • 6h 48m (2h 45m)
      • 1 Stop CLT · Charlotte 2h 45m
      • American Airlines (AA 1896)Airbus
        American Airlines (AA 1668)Boeing 737 Max 8 Passenger
      • American Airlines (AA 1896)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 05:10 MCO
        10:41 ORD
        6Hrs, 31m 1 Stop (ATL)
      • MCOOrlando International Airport 05:10 - ORD 10:41 6h 31m 1 Stop (ATL) Atlanta
      • MCOOrlando International Airport 05:10
        ATLAtlanta Hartsfield-Jackson Intl Airport 09:25
      • ATLAtlanta Hartsfield-Jackson Intl Airport 06:51
        ORDChicago O'Hare International Airport 10:41
      • 6h 31m (2h 34m)
      • 1 Stop ATL · Atlanta 2h 34m
      • Frontier Airlines (F9 1563)Airbus A321 Neo
        Frontier Airlines (F9 1441)Airbus A320 Neo
      • Frontier Airlines (F9 1563)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • 05:15 MCO
        10:58 ORD
        6Hrs, 43m 1 Stop (DFW)
      • MCOOrlando International Airport 05:15 - ORD 10:58 6h 43m 1 Stop (DFW) Dallas
      • MCOOrlando International Airport 05:15
        DFWDallas/Fort Worth Intl Airport 08:35
      • DFWDallas/Fort Worth Intl Airport 07:21
        ORDChicago O'Hare International Airport 10:58
      • 6h 43m (1h 14m)
      • 1 Stop DFW · Dallas 1h 14m
      • American Airlines (AA 2677)Airbus
        American Airlines (AA 328)Airbus
      • American Airlines (AA 2677)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:15 MCO
        10:56 ORD
        6Hrs, 41m 1 Stop (DFW)
      • MCOOrlando International Airport 05:15 - ORD 10:56 6h 41m 1 Stop (DFW) Dallas
      • MCOOrlando International Airport 05:15
        DFWDallas/Fort Worth Intl Airport 08:35
      • DFWDallas/Fort Worth Intl Airport 07:21
        ORDChicago O'Hare International Airport 10:56
      • 6h 41m (1h 14m)
      • 1 Stop DFW · Dallas 1h 14m
      • American Airlines (AA 2677)Airbus
        American Airlines (AA 328)Airbus
      • American Airlines (AA 2677)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 05:54 MCO
        11:45 ORD
        6Hrs, 51m 1 Stop (MIA)
      • MCOOrlando International Airport 05:54 - ORD 11:45 6h 51m 1 Stop (MIA) Miami
      • MCOOrlando International Airport 05:54
        MIAMiami International Airport 09:15
      • MIAMiami International Airport 07:06
        ORDChicago O'Hare International Airport 11:45
      • 6h 51m (2h 09m)
      • 1 Stop MIA · Miami 2h 09m
      • American Airlines (AA 2894)Airbus
        American Airlines (AA 2174)Boeing 737 800
      • American Airlines (AA 2894)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:54 MCO
        11:48 ORD
        6Hrs, 54m 1 Stop (MIA)
      • MCOOrlando International Airport 05:54 - ORD 11:48 6h 54m 1 Stop (MIA) Miami
      • MCOOrlando International Airport 05:54
        MIAMiami International Airport 09:18
      • MIAMiami International Airport 07:06
        ORDChicago O'Hare International Airport 11:48
      • 6h 54m (2h 12m)
      • 1 Stop MIA · Miami 2h 12m
      • American Airlines (AA 2894)Airbus
        American Airlines (AA 2174)Boeing 737 800
      • American Airlines (AA 2894)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:54 MCO
        11:03 ORD
        6Hrs, 09m 1 Stop (MIA)
      • MCOOrlando International Airport 05:54 - ORD 11:03 6h 09m 1 Stop (MIA) Miami
      • MCOOrlando International Airport 05:54
        MIAMiami International Airport 08:31
      • MIAMiami International Airport 07:06
        ORDChicago O'Hare International Airport 11:03
      • 6h 09m (1h 25m)
      • 1 Stop MIA · Miami 1h 25m
      • American Airlines (AA 2894)Airbus
        American Airlines (AA 1431)Boeing 737 800
      • American Airlines (AA 2894)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:54 MCO
        11:46 ORD
        6Hrs, 52m 1 Stop (MIA)
      • MCOOrlando International Airport 05:54 - ORD 11:46 6h 52m 1 Stop (MIA) Miami
      • MCOOrlando International Airport 05:54
        MIAMiami International Airport 09:15
      • MIAMiami International Airport 07:06
        ORDChicago O'Hare International Airport 11:46
      • 6h 52m (2h 09m)
      • 1 Stop MIA · Miami 2h 09m
      • American Airlines (AA 2894)Airbus
        American Airlines (AA 2174)Boeing 737 800
      • American Airlines (AA 2894)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:54 MCO
        11:02 ORD
        6Hrs, 08m 1 Stop (MIA)
      • MCOOrlando International Airport 05:54 - ORD 11:02 6h 08m 1 Stop (MIA) Miami
      • MCOOrlando International Airport 05:54
        MIAMiami International Airport 08:31
      • MIAMiami International Airport 07:06
        ORDChicago O'Hare International Airport 11:02
      • 6h 08m (1h 25m)
      • 1 Stop MIA · Miami 1h 25m
      • American Airlines (AA 2894)Airbus
        American Airlines (AA 1431)Boeing 737 800
      • American Airlines (AA 2894)
        • M
        • -
        • -
        • -
        • F
        • S
        • S
      • 06:00 MCO
        11:49 ORD
        6Hrs, 49m 1 Stop (EWR)
      • MCOOrlando International Airport 06:00 - ORD 11:49 6h 49m 1 Stop (EWR) New York City
      • MCOOrlando International Airport 06:00
        EWRNewark Liberty International Airport 10:15
      • EWRNewark Liberty International Airport 08:38
        ORDChicago O'Hare International Airport 11:49
      • 6h 49m (1h 37m)
      • 1 Stop EWR · New York City 1h 37m
      • United Airlines (UA 2607)Boeing 737 900
        United Airlines (UA 1525)Boeing 737 900
      • United Airlines (UA 2607)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 06:03 MCO
        10:48 ORD
        5Hrs, 45m 1 Stop (CLT)
      • MCOOrlando International Airport 06:03 - ORD 10:48 5h 45m 1 Stop (CLT) Charlotte
      • MCOOrlando International Airport 06:03
        CLTCharlotte Airport 09:33
      • CLTCharlotte Airport 07:52
        ORDChicago O'Hare International Airport 10:48
      • 5h 45m (1h 41m)
      • 1 Stop CLT · Charlotte 1h 41m
      • American Airlines (AA 461)Airbus
        American Airlines (AA 1668)Boeing 737 Max 8 Passenger
      • American Airlines (AA 461)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 06:03 MCO
        10:50 ORD
        5Hrs, 47m 1 Stop (CLT)
      • MCOOrlando International Airport 06:03 - ORD 10:50 5h 47m 1 Stop (CLT) Charlotte
      • MCOOrlando International Airport 06:03
        CLTCharlotte Airport 09:33
      • CLTCharlotte Airport 07:52
        ORDChicago O'Hare International Airport 10:50
      • 5h 47m (1h 41m)
      • 1 Stop CLT · Charlotte 1h 41m
      • American Airlines (AA 461)Airbus
        American Airlines (AA 1668)Boeing 737 Max 8 Passenger
      • American Airlines (AA 461)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:05 MCO
        11:15 MDW
        6Hrs, 10m 1 Stop (HOU)
      • MCOOrlando International Airport 06:05 - MDW 11:15 6h 10m 1 Stop (HOU) Houston
      • MCOOrlando International Airport 06:05
        HOUHouston Hobby Airport 08:50
      • HOUHouston Hobby Airport 07:50
        MDWChicago Midway Airport 11:15
      • 6h 10m (1h)
      • 1 Stop HOU · Houston 1h
      • Southwest Airlines (WN 735)Boeing 737 800
        Southwest Airlines (WN 222)Boeing 737 800
      • Southwest Airlines (WN 735)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:10 MCO
        10:15 MDW
        5Hrs, 05m 1 Stop (MSY)
      • MCOOrlando International Airport 06:10 - MDW 10:15 5h 05m 1 Stop (MSY) New Orleans
      • MCOOrlando International Airport 06:10
        MSYNew Orleans Louis Armstrong Intl Airport 08:00
      • MSYNew Orleans Louis Armstrong Intl Airport 07:10
        MDWChicago Midway Airport 10:15
      • 5h 05m (50m)
      • 1 Stop MSY · New Orleans 50m
      • Southwest Airlines (WN 667)Boeing 737 700
        Southwest Airlines (WN 736)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 667)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 06:15 MCO
        10:40 MDW
        5Hrs, 25m 1 Stop (BWI)
      • MCOOrlando International Airport 06:15 - MDW 10:40 5h 25m 1 Stop (BWI) Baltimore
      • MCOOrlando International Airport 06:15
        BWIBaltimore Washington International Airport 09:35
      • BWIBaltimore Washington International Airport 08:30
        MDWChicago Midway Airport 10:40
      • 5h 25m (1h 05m)
      • 1 Stop BWI · Baltimore 1h 05m
      • Southwest Airlines (WN 882)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 5265)Boeing 737 700
      • Southwest Airlines (WN 882)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:15 MCO
        11:30 ORD
        6Hrs, 15m 1 Stop (DAL)
      • MCOOrlando International Airport 06:15 - ORD 11:30 6h 15m 1 Stop (DAL) Dallas
      • MCOOrlando International Airport 06:15
        DALDallas/Fort Worth Love Field Airport 09:05
      • DALDallas/Fort Worth Love Field Airport 08:15
        ORDChicago O'Hare International Airport 11:30
      • 6h 15m (50m)
      • 1 Stop DAL · Dallas 50m
      • Southwest Airlines (WN 3289)Boeing 737 800
        Southwest Airlines (WN 309)Boeing 737 800
      • Southwest Airlines (WN 3289)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:20 MCO
        12:10 MDW
        6Hrs, 50m 1 Stop (AUS)
      • MCOOrlando International Airport 06:20 - MDW 12:10 6h 50m 1 Stop (AUS) Austin
      • MCOOrlando International Airport 06:20
        AUSAustin-Bergstrom International Airport 09:40
      • AUSAustin-Bergstrom International Airport 08:20
        MDWChicago Midway Airport 12:10
      • 6h 50m (1h 20m)
      • 1 Stop AUS · Austin 1h 20m
      • Southwest Airlines (WN 1766)Boeing 737 700
        Southwest Airlines (WN 2434)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1766)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:25 MCO
        12:20 MDW
        6Hrs, 55m 1 Stop (ATL)
      • MCOOrlando International Airport 06:25 - MDW 12:20 6h 55m 1 Stop (ATL) Atlanta
      • MCOOrlando International Airport 06:25
        ATLAtlanta Hartsfield-Jackson Intl Airport 11:25
      • ATLAtlanta Hartsfield-Jackson Intl Airport 08:05
        MDWChicago Midway Airport 12:20
      • 6h 55m (3h 20m)
      • 1 Stop ATL · Atlanta 3h 20m
      • Southwest Airlines (WN 2642)Boeing 737 700
        Southwest Airlines (WN 4846)Boeing 737 700
      • Southwest Airlines (WN 2642)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:30 MCO
        10:55 MDW
        5Hrs, 25m 1 Stop (MCI)
      • MCOOrlando International Airport 06:30 - MDW 10:55 5h 25m 1 Stop (MCI) Kansas City
      • MCOOrlando International Airport 06:30
        MCIKansas City International Airport 09:30
      • MCIKansas City International Airport 08:40
        MDWChicago Midway Airport 10:55
      • 5h 25m (50m)
      • 1 Stop MCI · Kansas City 50m
      • Southwest Airlines (WN 759)Boeing 737 700
        Southwest Airlines (WN 1031)Boeing 737 700
      • Southwest Airlines (WN 759)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:35 MCO
        11:45 MDW
        6Hrs, 10m 1 Stop (STL)
      • MCOOrlando International Airport 06:35 - MDW 11:45 6h 10m 1 Stop (STL) Saint Louis
      • MCOOrlando International Airport 06:35
        STLSt Louis Lambert Intl Airport 10:35
      • STLSt Louis Lambert Intl Airport 08:20
        MDWChicago Midway Airport 11:45
      • 6h 10m (2h 15m)
      • 1 Stop STL · Saint Louis 2h 15m
      • Southwest Airlines (WN 760)Boeing 737 800
        Southwest Airlines (WN 2364)Boeing 737 800
      • Southwest Airlines (WN 760)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:45 MCO
        11:10 MDW
        5Hrs, 25m 1 Stop (ATL)
      • MCOOrlando International Airport 06:45 - MDW 11:10 5h 25m 1 Stop (ATL) Atlanta
      • MCOOrlando International Airport 06:45
        ATLAtlanta Hartsfield-Jackson Intl Airport 10:08
      • ATLAtlanta Hartsfield-Jackson Intl Airport 08:36
        MDWChicago Midway Airport 11:10
      • 5h 25m (1h 32m)
      • 1 Stop ATL · Atlanta 1h 32m
      • Frontier Airlines (F9 1563)Airbus A320 Neo
        Frontier Airlines (F9 2143)Airbus A320 Neo
      • Frontier Airlines (F9 1563)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 06:50 MCO
        10:10 MDW
        4Hrs, 20m 1 Stop (ATL)
      • MCOOrlando International Airport 06:50 - MDW 10:10 4h 20m 1 Stop (ATL) Atlanta
      • MCOOrlando International Airport 06:50
        ATLAtlanta Hartsfield-Jackson Intl Airport 09:15
      • ATLAtlanta Hartsfield-Jackson Intl Airport 08:30
        MDWChicago Midway Airport 10:10
      • 4h 20m (45m)
      • 1 Stop ATL · Atlanta 45m
      • Southwest Airlines (WN 2642)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1925)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2642)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:50 MCO
        11:48 ORD
        5Hrs, 58m 1 Stop (MIA)
      • MCOOrlando International Airport 06:50 - ORD 11:48 5h 58m 1 Stop (MIA) Miami
      • MCOOrlando International Airport 06:50
        MIAMiami International Airport 09:18
      • MIAMiami International Airport 08:04
        ORDChicago O'Hare International Airport 11:48
      • 5h 58m (1h 14m)
      • 1 Stop MIA · Miami 1h 14m
      • American Airlines (AA 3165)Boeing 737 800
        American Airlines (AA 2174)Boeing 737 800
      • American Airlines (AA 3165)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:50 MCO
        11:46 ORD
        5Hrs, 56m 1 Stop (MIA)
      • MCOOrlando International Airport 06:50 - ORD 11:46 5h 56m 1 Stop (MIA) Miami
      • MCOOrlando International Airport 06:50
        MIAMiami International Airport 09:15
      • MIAMiami International Airport 08:04
        ORDChicago O'Hare International Airport 11:46
      • 5h 56m (1h 11m)
      • 1 Stop MIA · Miami 1h 11m
      • American Airlines (AA 3165)Boeing 737 800
        American Airlines (AA 2174)Boeing 737 800
      • American Airlines (AA 3165)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:50 MCO
        11:45 ORD
        5Hrs, 55m 1 Stop (MIA)
      • MCOOrlando International Airport 06:50 - ORD 11:45 5h 55m 1 Stop (MIA) Miami
      • MCOOrlando International Airport 06:50
        MIAMiami International Airport 09:15
      • MIAMiami International Airport 08:04
        ORDChicago O'Hare International Airport 11:45
      • 5h 55m (1h 11m)
      • 1 Stop MIA · Miami 1h 11m
      • American Airlines (AA 3165)Boeing 737 800
        American Airlines (AA 2174)Boeing 737 800
      • American Airlines (AA 3165)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:51 MCO
        12:25 ORD
        6Hrs, 34m 1 Stop (DFW)
      • MCOOrlando International Airport 06:51 - ORD 12:25 6h 34m 1 Stop (DFW) Dallas
      • MCOOrlando International Airport 06:51
        DFWDallas/Fort Worth Intl Airport 10:00
      • DFWDallas/Fort Worth Intl Airport 08:58
        ORDChicago O'Hare International Airport 12:25
      • 6h 34m (1h 02m)
      • 1 Stop DFW · Dallas 1h 02m
      • American Airlines (AA 668)Airbus
        American Airlines (AA 2754)Boeing 737 800
      • American Airlines (AA 668)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:51 MCO
        12:33 ORD
        6Hrs, 42m 1 Stop (DFW)
      • MCOOrlando International Airport 06:51 - ORD 12:33 6h 42m 1 Stop (DFW) Dallas
      • MCOOrlando International Airport 06:51
        DFWDallas/Fort Worth Intl Airport 10:00
      • DFWDallas/Fort Worth Intl Airport 08:58
        ORDChicago O'Hare International Airport 12:33
      • 6h 42m (1h 02m)
      • 1 Stop DFW · Dallas 1h 02m
      • American Airlines (AA 668)Airbus
        American Airlines (AA 2754)Airbus
      • American Airlines (AA 668)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 06:51 MCO
        12:29 ORD
        6Hrs, 38m 1 Stop (DFW)
      • MCOOrlando International Airport 06:51 - ORD 12:29 6h 38m 1 Stop (DFW) Dallas
      • MCOOrlando International Airport 06:51
        DFWDallas/Fort Worth Intl Airport 10:00
      • DFWDallas/Fort Worth Intl Airport 08:58
        ORDChicago O'Hare International Airport 12:29
      • 6h 38m (1h 02m)
      • 1 Stop DFW · Dallas 1h 02m
      • American Airlines (AA 668)Airbus
        American Airlines (AA 2754)Boeing 737 800
      • American Airlines (AA 668)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
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      What’s the fastest flight time from Orlando to Chicago?

      The fastest flight time for direct flights from Orlando to Chicago is 2 hours 45 minutes. Check latest flight schedules & prices on Wego.

      What’s the most popular airline flying from Orlando to Chicago?

      The most popular airline flying from Orlando to Chicago is American Airlines. Find the latest flight deals on Wego.

      How far is Chicago from Orlando?

      The flight distance between Orlando and Chicago is 1587km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 05:00. The last flight of the day departs at 19:05. See the full list of flight times on Wego.

      How many airlines offer direct flights from Orlando to Chicago?

      There are 6 airlines that offer direct flights from Orlando to Chicago. Find out the list of airlines on Wego.

      Popular Airlines flying from Orlando to Chicago

      American Airlines ‏()
      Frontier Airlines ‏()
      Spirit Airlines ‏()
      United Airlines ‏()

      Popular Destinations from Chicago

      Popular Destinations from Orlando

      Popular Hotels in Chicago

      Hotels In Popular Destinations