Flight Schedules

Last Updated: Wed, 2 Oct, 2024

  • Time Earliest
    • Earliest
    • Latest
  • Depart Earliest
    • Earliest
    • Latest
  • Arrive
    • Earliest
    • Latest
  • Duration
    • Shortest
    • Longest
  • Stopover
    All
  • Airline Filter by Airline
    View All Airline
  • Availability
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • 06:05 RSW
    07:55 MDW
    2Hrs, 50m Direct
  • RSWSouthwest Florida International Airport 06:05 - MDW 07:55 2h 50m Direct
  • RSWSouthwest Florida International Airport 06:05
  • MDWChicago Midway Airport 07:55
  • 2h 50m
  • Direct
  • Southwest Airlines (WN 2874)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 2874)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 Max 8 Passenger
  • 06:30 RSW
    08:20 MDW
    2Hrs, 50m Direct
  • RSWSouthwest Florida International Airport 06:30 - MDW 08:20 2h 50m Direct
  • RSWSouthwest Florida International Airport 06:30
  • MDWChicago Midway Airport 08:20
  • 2h 50m
  • Direct
  • Southwest Airlines (WN 1204)Boeing 737 800
  • Southwest Airlines (WN 1204)
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 800
  • 06:30 RSW
    08:20 MDW
    2Hrs, 50m Direct
  • RSWSouthwest Florida International Airport 06:30 - MDW 08:20 2h 50m Direct
  • RSWSouthwest Florida International Airport 06:30
  • MDWChicago Midway Airport 08:20
  • 2h 50m
  • Direct
  • Southwest Airlines (WN 1204)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 1204)
    • -
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 07:05 RSW
    08:55 MDW
    2Hrs, 50m Direct
  • RSWSouthwest Florida International Airport 07:05 - MDW 08:55 2h 50m Direct
  • RSWSouthwest Florida International Airport 07:05
  • MDWChicago Midway Airport 08:55
  • 2h 50m
  • Direct
  • Southwest Airlines (WN 4350)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 4350)
    • M
    • -
    • -
    • -
    • -
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 07:10 RSW
    09:00 MDW
    2Hrs, 50m Direct
  • RSWSouthwest Florida International Airport 07:10 - MDW 09:00 2h 50m Direct
  • RSWSouthwest Florida International Airport 07:10
  • MDWChicago Midway Airport 09:00
  • 2h 50m
  • Direct
  • Southwest Airlines (WN 4350)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 4350)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 07:40 RSW
    09:43 ORD
    3Hrs, 03m Direct
  • RSWSouthwest Florida International Airport 07:40 - ORD 09:43 3h 03m Direct
  • RSWSouthwest Florida International Airport 07:40
  • ORDChicago O'Hare International Airport 09:43
  • 3h 03m
  • Direct
  • United Airlines (UA 2341)Boeing 737 900
  • United Airlines (UA 2341)
    • -
    • -
    • -
    • -
    • F
    • -
    • -
  • Boeing 737 900
  • 07:45 RSW
    09:55 ORD
    3Hrs, 10m Direct
  • RSWSouthwest Florida International Airport 07:45 - ORD 09:55 3h 10m Direct
  • RSWSouthwest Florida International Airport 07:45
  • ORDChicago O'Hare International Airport 09:55
  • 3h 10m
  • Direct
  • United Airlines (UA 2341)Boeing 737 900
  • United Airlines (UA 2341)
    • -
    • -
    • -
    • T
    • -
    • S
    • S
  • Boeing 737 900
  • 07:45 RSW
    09:55 ORD
    3Hrs, 10m Direct
  • RSWSouthwest Florida International Airport 07:45 - ORD 09:55 3h 10m Direct
  • RSWSouthwest Florida International Airport 07:45
  • ORDChicago O'Hare International Airport 09:55
  • 3h 10m
  • Direct
  • United Airlines (UA 1097)Boeing 737 900
  • United Airlines (UA 1097)
    • M
    • -
    • -
    • -
    • -
    • -
    • -
  • Boeing 737 900
  • 09:35 RSW
    12:45 MDW
    4Hrs, 10m Direct
  • RSWSouthwest Florida International Airport 09:35 - MDW 12:45 4h 10m Direct
  • RSWSouthwest Florida International Airport 09:35
  • MDWChicago Midway Airport 12:45
  • 4h 10m
  • Direct
  • Southwest Airlines (WN 792)Boeing 737 700
  • Southwest Airlines (WN 792)
    • -
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 700
  • 11:00 RSW
    12:55 MDW
    2Hrs, 55m Direct
  • RSWSouthwest Florida International Airport 11:00 - MDW 12:55 2h 55m Direct
  • RSWSouthwest Florida International Airport 11:00
  • MDWChicago Midway Airport 12:55
  • 2h 55m
  • Direct
  • Southwest Airlines (WN 1204)Boeing 737 700
  • Southwest Airlines (WN 1204)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 700
  • 11:50 RSW
    13:40 MDW
    2Hrs, 50m Direct
  • RSWSouthwest Florida International Airport 11:50 - MDW 13:40 2h 50m Direct
  • RSWSouthwest Florida International Airport 11:50
  • MDWChicago Midway Airport 13:40
  • 2h 50m
  • Direct
  • Southwest Airlines (WN 1426)Boeing 737 800
  • Southwest Airlines (WN 1426)
    • M
    • -
    • -
    • -
    • -
    • -
    • -
  • Boeing 737 800
  • 12:00 RSW
    15:30 MDW
    4Hrs, 30m Direct
  • RSWSouthwest Florida International Airport 12:00 - MDW 15:30 4h 30m Direct
  • RSWSouthwest Florida International Airport 12:00
  • MDWChicago Midway Airport 15:30
  • 4h 30m
  • Direct
  • Southwest Airlines (WN 378)Boeing 737 700
  • Southwest Airlines (WN 378)
    • -
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 700
  • 12:35 RSW
    14:25 MDW
    2Hrs, 50m Direct
  • RSWSouthwest Florida International Airport 12:35 - MDW 14:25 2h 50m Direct
  • RSWSouthwest Florida International Airport 12:35
  • MDWChicago Midway Airport 14:25
  • 2h 50m
  • Direct
  • Southwest Airlines (WN 2874)Boeing 737 700
  • Southwest Airlines (WN 2874)
    • -
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 700
  • 12:40 RSW
    14:50 ORD
    3Hrs, 10m Direct
  • RSWSouthwest Florida International Airport 12:40 - ORD 14:50 3h 10m Direct
  • RSWSouthwest Florida International Airport 12:40
  • ORDChicago O'Hare International Airport 14:50
  • 3h 10m
  • Direct
  • United Airlines (UA 511)Boeing 737 900
  • United Airlines (UA 511)
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 900
  • 12:40 RSW
    14:50 ORD
    3Hrs, 10m Direct
  • RSWSouthwest Florida International Airport 12:40 - ORD 14:50 3h 10m Direct
  • RSWSouthwest Florida International Airport 12:40
  • ORDChicago O'Hare International Airport 14:50
  • 3h 10m
  • Direct
  • United Airlines (UA 511)Boeing 737 Max 8 Passenger
  • United Airlines (UA 511)
    • M
    • T
    • W
    • T
    • F
    • S
    • -
  • Boeing 737 Max 8 Passenger
  • 13:00 RSW
    14:55 MDW
    2Hrs, 55m Direct
  • RSWSouthwest Florida International Airport 13:00 - MDW 14:55 2h 55m Direct
  • RSWSouthwest Florida International Airport 13:00
  • MDWChicago Midway Airport 14:55
  • 2h 55m
  • Direct
  • Southwest Airlines (WN 1439)Boeing 737 800
  • Southwest Airlines (WN 1439)
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 800
  • 13:05 RSW
    15:14 ORD
    3Hrs, 09m Direct
  • RSWSouthwest Florida International Airport 13:05 - ORD 15:14 3h 09m Direct
  • RSWSouthwest Florida International Airport 13:05
  • ORDChicago O'Hare International Airport 15:14
  • 3h 09m
  • Direct
  • American Airlines (AA 1929)Boeing 737 800
  • American Airlines (AA 1929)
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Boeing 737 800
  • 14:30 RSW
    16:40 ORD
    3Hrs, 10m Direct
  • RSWSouthwest Florida International Airport 14:30 - ORD 16:40 3h 10m Direct
  • RSWSouthwest Florida International Airport 14:30
  • ORDChicago O'Hare International Airport 16:40
  • 3h 10m
  • Direct
  • United Airlines (UA 2605)Boeing 737 800
  • United Airlines (UA 2605)
    • -
    • -
    • -
    • T
    • -
    • S
    • S
  • Boeing 737 800
  • 14:34 RSW
    16:44 ORD
    3Hrs, 10m Direct
  • RSWSouthwest Florida International Airport 14:34 - ORD 16:44 3h 10m Direct
  • RSWSouthwest Florida International Airport 14:34
  • ORDChicago O'Hare International Airport 16:44
  • 3h 10m
  • Direct
  • United Airlines (UA 2605)Boeing 737 800
  • United Airlines (UA 2605)
    • M
    • T
    • -
    • -
    • -
    • -
    • -
  • Boeing 737 800
  • 14:34 RSW
    16:44 ORD
    3Hrs, 10m Direct
  • RSWSouthwest Florida International Airport 14:34 - ORD 16:44 3h 10m Direct
  • RSWSouthwest Florida International Airport 14:34
  • ORDChicago O'Hare International Airport 16:44
  • 3h 10m
  • Direct
  • United Airlines (UA 2605)Boeing 737 900
  • United Airlines (UA 2605)
    • -
    • -
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 900
  • 16:15 RSW
    18:10 MDW
    2Hrs, 55m Direct
  • RSWSouthwest Florida International Airport 16:15 - MDW 18:10 2h 55m Direct
  • RSWSouthwest Florida International Airport 16:15
  • MDWChicago Midway Airport 18:10
  • 2h 55m
  • Direct
  • Southwest Airlines (WN 4349)Boeing 737 700
  • Southwest Airlines (WN 4349)
    • M
    • -
    • -
    • -
    • -
    • -
    • -
  • Boeing 737 700
  • 16:45 RSW
    18:35 MDW
    2Hrs, 50m Direct
  • RSWSouthwest Florida International Airport 16:45 - MDW 18:35 2h 50m Direct
  • RSWSouthwest Florida International Airport 16:45
  • MDWChicago Midway Airport 18:35
  • 2h 50m
  • Direct
  • Southwest Airlines (WN 4349)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 4349)
    • -
    • -
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 16:50 RSW
    18:40 MDW
    2Hrs, 50m Direct
  • RSWSouthwest Florida International Airport 16:50 - MDW 18:40 2h 50m Direct
  • RSWSouthwest Florida International Airport 16:50
  • MDWChicago Midway Airport 18:40
  • 2h 50m
  • Direct
  • Southwest Airlines (WN 4349)Boeing 737 800
  • Southwest Airlines (WN 4349)
    • -
    • T
    • -
    • -
    • -
    • -
    • -
  • Boeing 737 800
  • 16:50 RSW
    18:45 MDW
    2Hrs, 55m Direct
  • RSWSouthwest Florida International Airport 16:50 - MDW 18:45 2h 55m Direct
  • RSWSouthwest Florida International Airport 16:50
  • MDWChicago Midway Airport 18:45
  • 2h 55m
  • Direct
  • Southwest Airlines (WN 1401)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 1401)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 Max 8 Passenger
  • 18:00 RSW
    20:14 ORD
    3Hrs, 14m Direct
  • RSWSouthwest Florida International Airport 18:00 - ORD 20:14 3h 14m Direct
  • RSWSouthwest Florida International Airport 18:00
  • ORDChicago O'Hare International Airport 20:14
  • 3h 14m
  • Direct
  • United Airlines (UA 1748)Boeing 737 800
  • United Airlines (UA 1748)
    • M
    • -
    • -
    • -
    • -
    • -
    • -
  • Boeing 737 800
  • 18:01 RSW
    20:15 ORD
    3Hrs, 14m Direct
  • RSWSouthwest Florida International Airport 18:01 - ORD 20:15 3h 14m Direct
  • RSWSouthwest Florida International Airport 18:01
  • ORDChicago O'Hare International Airport 20:15
  • 3h 14m
  • Direct
  • United Airlines (UA 1748)Boeing 737 800
  • United Airlines (UA 1748)
    • -
    • T
    • W
    • -
    • F
    • S
    • S
  • Boeing 737 800
  • 18:01 RSW
    20:15 ORD
    3Hrs, 14m Direct
  • RSWSouthwest Florida International Airport 18:01 - ORD 20:15 3h 14m Direct
  • RSWSouthwest Florida International Airport 18:01
  • ORDChicago O'Hare International Airport 20:15
  • 3h 14m
  • Direct
  • United Airlines (UA 1748)Boeing 737 900
  • United Airlines (UA 1748)
    • -
    • -
    • -
    • T
    • -
    • -
    • -
  • Boeing 737 900
  • 19:35 RSW
    21:25 MDW
    2Hrs, 50m Direct
  • RSWSouthwest Florida International Airport 19:35 - MDW 21:25 2h 50m Direct
  • RSWSouthwest Florida International Airport 19:35
  • MDWChicago Midway Airport 21:25
  • 2h 50m
  • Direct
  • Southwest Airlines (WN 1401)Boeing 737 800
  • Southwest Airlines (WN 1401)
    • -
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 800
  • 19:40 RSW
    21:30 MDW
    2Hrs, 50m Direct
  • RSWSouthwest Florida International Airport 19:40 - MDW 21:30 2h 50m Direct
  • RSWSouthwest Florida International Airport 19:40
  • MDWChicago Midway Airport 21:30
  • 2h 50m
  • Direct
  • Southwest Airlines (WN 1401)Boeing 737 700
  • Southwest Airlines (WN 1401)
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 700
No Schedules Sorry, there are no schedules matching your filters. Try removing one. reset
What’s the fastest flight time from Fort Myers to Chicago?

The fastest flight time for direct flights from Fort Myers to Chicago is 2 hours 50 minutes. Check latest flight schedules & prices on Wego.

How far is Chicago from Fort Myers?

The flight distance between Fort Myers and Chicago is 1774km. Check all available flights on Wego.

When is the earliest and latest flight of the day?

The earliest flight of the day departs at 06:05. The last flight of the day departs at 06:05. See the full list of flight times on Wego.

How many airlines offer direct flights from Fort Myers to Chicago?

There are 3 airlines that offer direct flights from Fort Myers to Chicago. Find out the list of airlines on Wego.