Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Alaska Airlines
Cheapest Month May
Cheapest Day of the Week Friday
Cheapest Airline Alaska Airlines

The cheapest airline(s) flying from Chicago to San Diego is Alaska Airlines.

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

Travel Period: May 2025 - April 2026

The cheapest month(s) to fly from Chicago to San Diego is May.

  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
  • Dec 2025
  • Jan 2026
  • Feb 2026
  • Mar 2026
  • Apr 2026
Cheapest Day of the Week Friday

The cheapest day(s) of the week to fly from Chicago to San Diego is Friday.

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

Flight Schedules

Last Updated: Wed, 2 Apr, 2025

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    • Airline Filter by Airline
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      • Availability
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 19:50 ORD
        22:29 SAN
        4Hrs, 39m Direct
      • ORDChicago O'Hare International Airport 19:50 - SAN 22:29 4h 39m Direct
      • ORDChicago O'Hare International Airport 19:50
      • SANSan Diego International Airport 22:29
      • 4h 39m
      • Direct
      • United Airlines (UA 2718)Boeing 737 800
      • United Airlines (UA 2718)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • Boeing 737 800
      • 19:56 ORD
        22:35 SAN
        4Hrs, 39m Direct
      • ORDChicago O'Hare International Airport 19:56 - SAN 22:35 4h 39m Direct
      • ORDChicago O'Hare International Airport 19:56
      • SANSan Diego International Airport 22:35
      • 4h 39m
      • Direct
      • United Airlines (UA 2718)Boeing 737 800
      • United Airlines (UA 2718)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 20:25 MDW
        22:45 SAN
        4Hrs, 20m Direct
      • MDWChicago Midway Airport 20:25 - SAN 22:45 4h 20m Direct
      • MDWChicago Midway Airport 20:25
      • SANSan Diego International Airport 22:45
      • 4h 20m
      • Direct
      • Southwest Airlines (WN 404)Boeing 737 700
      • Southwest Airlines (WN 404)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 20:35 MDW
        22:55 SAN
        4Hrs, 20m Direct
      • MDWChicago Midway Airport 20:35 - SAN 22:55 4h 20m Direct
      • MDWChicago Midway Airport 20:35
      • SANSan Diego International Airport 22:55
      • 4h 20m
      • Direct
      • Southwest Airlines (WN 548)Boeing 737 700
      • Southwest Airlines (WN 548)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 20:55 MDW
        23:15 SAN
        4Hrs, 20m Direct
      • MDWChicago Midway Airport 20:55 - SAN 23:15 4h 20m Direct
      • MDWChicago Midway Airport 20:55
      • SANSan Diego International Airport 23:15
      • 4h 20m
      • Direct
      • Southwest Airlines (WN 1899)Boeing 737 700
      • Southwest Airlines (WN 1899)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 700
      • 21:04 ORD
        23:28 SAN
        4Hrs, 24m Direct
      • ORDChicago O'Hare International Airport 21:04 - SAN 23:28 4h 24m Direct
      • ORDChicago O'Hare International Airport 21:04
      • SANSan Diego International Airport 23:28
      • 4h 24m
      • Direct
      • American Airlines (AA 1861)Airbus
      • American Airlines (AA 1861)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Airbus
      • 06:50 ORD
        09:19 SAN
        4Hrs, 29m Direct
      • ORDChicago O'Hare International Airport 06:50 - SAN 09:19 4h 29m Direct
      • ORDChicago O'Hare International Airport 06:50
      • SANSan Diego International Airport 09:19
      • 4h 29m
      • Direct
      • American Airlines (AA 2131)Boeing 737 800
      • American Airlines (AA 2131)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • Boeing 737 800
      • 07:05 MDW
        10:50 SAN
        5Hrs, 45m Direct
      • MDWChicago Midway Airport 07:05 - SAN 10:50 5h 45m Direct
      • MDWChicago Midway Airport 07:05
      • SANSan Diego International Airport 10:50
      • 5h 45m
      • Direct
      • Southwest Airlines (WN 5830)Boeing 737 700
      • Southwest Airlines (WN 5830)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 700
      • 08:05 MDW
        10:25 SAN
        4Hrs, 20m Direct
      • MDWChicago Midway Airport 08:05 - SAN 10:25 4h 20m Direct
      • MDWChicago Midway Airport 08:05
      • SANSan Diego International Airport 10:25
      • 4h 20m
      • Direct
      • Southwest Airlines (WN 2283)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2283)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 08:05 MDW
        10:25 SAN
        4Hrs, 20m Direct
      • MDWChicago Midway Airport 08:05 - SAN 10:25 4h 20m Direct
      • MDWChicago Midway Airport 08:05
      • SANSan Diego International Airport 10:25
      • 4h 20m
      • Direct
      • Southwest Airlines (WN 3175)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3175)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 08:20 MDW
        14:25 SAN
        8Hrs, 05m Direct
      • MDWChicago Midway Airport 08:20 - SAN 14:25 8h 05m Direct
      • MDWChicago Midway Airport 08:20
      • SANSan Diego International Airport 14:25
      • 8h 05m
      • Direct
      • Southwest Airlines (WN 1681)Boeing 737 700
      • Southwest Airlines (WN 1681)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 700
      • 08:20 MDW
        10:40 SAN
        4Hrs, 20m Direct
      • MDWChicago Midway Airport 08:20 - SAN 10:40 4h 20m Direct
      • MDWChicago Midway Airport 08:20
      • SANSan Diego International Airport 10:40
      • 4h 20m
      • Direct
      • Southwest Airlines (WN 3175)Boeing 737 700
      • Southwest Airlines (WN 3175)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 08:35 MDW
        11:00 SAN
        4Hrs, 25m Direct
      • MDWChicago Midway Airport 08:35 - SAN 11:00 4h 25m Direct
      • MDWChicago Midway Airport 08:35
      • SANSan Diego International Airport 11:00
      • 4h 25m
      • Direct
      • Southwest Airlines (WN 3627)Boeing 737 700
      • Southwest Airlines (WN 3627)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 09:05 ORD
        11:42 SAN
        4Hrs, 37m Direct
      • ORDChicago O'Hare International Airport 09:05 - SAN 11:42 4h 37m Direct
      • ORDChicago O'Hare International Airport 09:05
      • SANSan Diego International Airport 11:42
      • 4h 37m
      • Direct
      • United Airlines (UA 660)Airbus A321 Neo
      • United Airlines (UA 660)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Airbus A321 Neo
      • 10:12 ORD
        12:43 SAN
        4Hrs, 31m Direct
      • ORDChicago O'Hare International Airport 10:12 - SAN 12:43 4h 31m Direct
      • ORDChicago O'Hare International Airport 10:12
      • SANSan Diego International Airport 12:43
      • 4h 31m
      • Direct
      • American Airlines (AA 2189)Boeing 737 800
      • American Airlines (AA 2189)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 11:20 ORD
        13:56 SAN
        4Hrs, 36m Direct
      • ORDChicago O'Hare International Airport 11:20 - SAN 13:56 4h 36m Direct
      • ORDChicago O'Hare International Airport 11:20
      • SANSan Diego International Airport 13:56
      • 4h 36m
      • Direct
      • United Airlines (UA 2294)Boeing 737 800
      • United Airlines (UA 2294)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 11:55 MDW
        14:10 SAN
        4Hrs, 15m Direct
      • MDWChicago Midway Airport 11:55 - SAN 14:10 4h 15m Direct
      • MDWChicago Midway Airport 11:55
      • SANSan Diego International Airport 14:10
      • 4h 15m
      • Direct
      • Southwest Airlines (WN 3627)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3627)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 12:35 MDW
        14:55 SAN
        4Hrs, 20m Direct
      • MDWChicago Midway Airport 12:35 - SAN 14:55 4h 20m Direct
      • MDWChicago Midway Airport 12:35
      • SANSan Diego International Airport 14:55
      • 4h 20m
      • Direct
      • Southwest Airlines (WN 3627)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3627)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 12:35 MDW
        16:25 SAN
        5Hrs, 50m Direct
      • MDWChicago Midway Airport 12:35 - SAN 16:25 5h 50m Direct
      • MDWChicago Midway Airport 12:35
      • SANSan Diego International Airport 16:25
      • 5h 50m
      • Direct
      • Southwest Airlines (WN 482)Boeing 737 700
      • Southwest Airlines (WN 482)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 13:44 ORD
        16:17 SAN
        4Hrs, 33m Direct
      • ORDChicago O'Hare International Airport 13:44 - SAN 16:17 4h 33m Direct
      • ORDChicago O'Hare International Airport 13:44
      • SANSan Diego International Airport 16:17
      • 4h 33m
      • Direct
      • United Airlines (UA 2683)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2683)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 Max 8 Passenger
      • 14:18 ORD
        20:22 SAN
        8Hrs, 04m Direct
      • ORDChicago O'Hare International Airport 14:18 - SAN 20:22 8h 04m Direct
      • ORDChicago O'Hare International Airport 14:18
      • SANSan Diego International Airport 20:22
      • 8h 04m
      • Direct
      • United Airlines (UA 1373)Airbus A321 Neo
      • United Airlines (UA 1373)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Airbus A321 Neo
      • 14:18 ORD
        20:22 SAN
        8Hrs, 04m Direct
      • ORDChicago O'Hare International Airport 14:18 - SAN 20:22 8h 04m Direct
      • ORDChicago O'Hare International Airport 14:18
      • SANSan Diego International Airport 20:22
      • 8h 04m
      • Direct
      • United Airlines (UA 1373)Boeing 757 300 Series
      • United Airlines (UA 1373)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • Boeing 757 300 Series
      • 14:20 MDW
        16:40 SAN
        4Hrs, 20m Direct
      • MDWChicago Midway Airport 14:20 - SAN 16:40 4h 20m Direct
      • MDWChicago Midway Airport 14:20
      • SANSan Diego International Airport 16:40
      • 4h 20m
      • Direct
      • Southwest Airlines (WN 2283)Boeing 737 700
      • Southwest Airlines (WN 2283)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 14:25 MDW
        18:00 SAN
        5Hrs, 35m Direct
      • MDWChicago Midway Airport 14:25 - SAN 18:00 5h 35m Direct
      • MDWChicago Midway Airport 14:25
      • SANSan Diego International Airport 18:00
      • 5h 35m
      • Direct
      • Southwest Airlines (WN 1459)Boeing 737 700
      • Southwest Airlines (WN 1459)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 14:55 ORD
        18:40 SAN
        5Hrs, 45m Direct
      • ORDChicago O'Hare International Airport 14:55 - SAN 18:40 5h 45m Direct
      • ORDChicago O'Hare International Airport 14:55
      • SANSan Diego International Airport 18:40
      • 5h 45m
      • Direct
      • Southwest Airlines (WN 643)Boeing 737 700
      • Southwest Airlines (WN 643)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 700
      • 16:20 ORD
        18:56 SAN
        4Hrs, 36m Direct
      • ORDChicago O'Hare International Airport 16:20 - SAN 18:56 4h 36m Direct
      • ORDChicago O'Hare International Airport 16:20
      • SANSan Diego International Airport 18:56
      • 4h 36m
      • Direct
      • United Airlines (UA 2331)Airbus A321 Neo
      • United Airlines (UA 2331)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Airbus A321 Neo
      • 16:45 MDW
        19:05 SAN
        4Hrs, 20m Direct
      • MDWChicago Midway Airport 16:45 - SAN 19:05 4h 20m Direct
      • MDWChicago Midway Airport 16:45
      • SANSan Diego International Airport 19:05
      • 4h 20m
      • Direct
      • Southwest Airlines (WN 1372)Boeing 737 700
      • Southwest Airlines (WN 1372)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 16:55 ORD
        19:14 SAN
        4Hrs, 19m Direct
      • ORDChicago O'Hare International Airport 16:55 - SAN 19:14 4h 19m Direct
      • ORDChicago O'Hare International Airport 16:55
      • SANSan Diego International Airport 19:14
      • 4h 19m
      • Direct
      • American Airlines (AA 1543)Airbus
      • American Airlines (AA 1543)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • Airbus
      • 16:55 ORD
        19:22 SAN
        4Hrs, 27m Direct
      • ORDChicago O'Hare International Airport 16:55 - SAN 19:22 4h 27m Direct
      • ORDChicago O'Hare International Airport 16:55
      • SANSan Diego International Airport 19:22
      • 4h 27m
      • Direct
      • American Airlines (AA 1543)Boeing 737 800
      • American Airlines (AA 1543)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 17:07 ORD
        19:34 SAN
        4Hrs, 27m Direct
      • ORDChicago O'Hare International Airport 17:07 - SAN 19:34 4h 27m Direct
      • ORDChicago O'Hare International Airport 17:07
      • SANSan Diego International Airport 19:34
      • 4h 27m
      • Direct
      • American Airlines (AA 1543)Boeing 737 800
      • American Airlines (AA 1543)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 17:07 ORD
        19:27 SAN
        4Hrs, 20m Direct
      • ORDChicago O'Hare International Airport 17:07 - SAN 19:27 4h 20m Direct
      • ORDChicago O'Hare International Airport 17:07
      • SANSan Diego International Airport 19:27
      • 4h 20m
      • Direct
      • American Airlines (AA 1543)Airbus
      • American Airlines (AA 1543)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • Airbus
      • 19:05 MDW
        23:10 SAN
        6Hrs, 05m 1 Stop (LAS)
      • MDWChicago Midway Airport 19:05 - SAN 23:10 6h 05m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 19:05
        LASLas Vegas McCarran International Airport 22:00
      • LASLas Vegas McCarran International Airport 21:00
        SANSan Diego International Airport 23:10
      • 6h 05m (1h)
      • 1 Stop LAS · Las Vegas 1h
      • Southwest Airlines (WN 2190)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 5210)Boeing 737 700
      • Southwest Airlines (WN 2190)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 19:12 ORD
        00:42 SAN
        7Hrs, 30m 1 Stop (LAS)
      • ORDChicago O'Hare International Airport 19:12 - SAN 00:42 7h 30m 1 Stop (LAS) Las Vegas
      • ORDChicago O'Hare International Airport 19:12
        LASLas Vegas McCarran International Airport 23:25
      • LASLas Vegas McCarran International Airport 21:20
        SANSan Diego International Airport 00:42
      • 7h 30m (2h 05m)
      • 1 Stop LAS · Las Vegas 2h 05m
      • Spirit Airlines (NK 388)Airbus A320 Neo
        Spirit Airlines (NK 385)Airbus Industrie A320 Sharklets
      • Spirit Airlines (NK 388)
        • -
        • -
        • -
        • T
        • -
        • -
        • S
      • 20:01 MDW
        00:14 SAN
        6Hrs, 13m 1 Stop (DEN)
      • MDWChicago Midway Airport 20:01 - SAN 00:14 6h 13m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 20:01
        DENDenver Intl Airport 22:43
      • DENDenver Intl Airport 21:49
        SANSan Diego International Airport 00:14
      • 6h 13m (54m)
      • 1 Stop DEN · Denver 54m
      • Frontier Airlines (F9 2209)Airbus A320 Neo
        Frontier Airlines (F9 2711)Airbus A320 Neo
      • Frontier Airlines (F9 2209)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:00 ORD
        09:24 SAN
        6Hrs, 24m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 05:00 - SAN 09:24 6h 24m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 05:00
        DENDenver Intl Airport 07:58
      • DENDenver Intl Airport 06:50
        SANSan Diego International Airport 09:24
      • 6h 24m (1h 08m)
      • 1 Stop DEN · Denver 1h 08m
      • United Airlines (UA 2666)Airbus A321 Neo
        United Airlines (UA 2309)Boeing 737 800
      • United Airlines (UA 2666)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 05:00 ORD
        10:01 SAN
        7Hrs, 01m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 05:00 - SAN 10:01 7h 01m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 08:50
      • DFWDallas/Fort Worth Intl Airport 07:39
        SANSan Diego International Airport 10:01
      • 7h 01m (1h 11m)
      • 1 Stop DFW · Dallas 1h 11m
      • American Airlines (AA 760)Boeing 737 800
        American Airlines (AA 2050)Airbus
      • American Airlines (AA 760)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 05:00 ORD
        10:10 SAN
        7Hrs, 10m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 05:00 - SAN 10:10 7h 10m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 08:55
      • DFWDallas/Fort Worth Intl Airport 07:39
        SANSan Diego International Airport 10:10
      • 7h 10m (1h 16m)
      • 1 Stop DFW · Dallas 1h 16m
      • American Airlines (AA 760)Boeing 737 800
        American Airlines (AA 2050)Boeing 737 800
      • American Airlines (AA 760)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:05 MDW
        09:40 SAN
        6Hrs, 35m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:05 - SAN 09:40 6h 35m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:05
        PHXPhoenix Sky Harbor Intl Airport 08:25
      • PHXPhoenix Sky Harbor Intl Airport 06:50
        SANSan Diego International Airport 09:40
      • 6h 35m (1h 35m)
      • 1 Stop PHX · Phoenix 1h 35m
      • Southwest Airlines (WN 2811)Boeing 737 700
        Southwest Airlines (WN 1432)Boeing 737 700
      • Southwest Airlines (WN 2811)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 05:05 MDW
        11:20 SAN
        8Hrs, 15m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:05 - SAN 11:20 8h 15m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:05
        PHXPhoenix Sky Harbor Intl Airport 10:05
      • PHXPhoenix Sky Harbor Intl Airport 06:50
        SANSan Diego International Airport 11:20
      • 8h 15m (3h 15m)
      • 1 Stop PHX · Phoenix 3h 15m
      • Southwest Airlines (WN 2811)Boeing 737 700
        Southwest Airlines (WN 1762)Boeing 737 700
      • Southwest Airlines (WN 2811)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 05:10 MDW
        10:30 SAN
        7Hrs, 20m 1 Stop (DAL)
      • MDWChicago Midway Airport 05:10 - SAN 10:30 7h 20m 1 Stop (DAL)
      • MDWChicago Midway Airport 05:10
        DALDallas/Fort Worth Love Field Airport 09:15
      • DALDallas/Fort Worth Love Field Airport 07:30
        SANSan Diego International Airport 10:30
      • 7h 20m (1h 45m)
      • 1 Stop DAL · 1h 45m
      • Southwest Airlines (WN 2332)Boeing 737 800
        Southwest Airlines (WN 2197)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2332)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 05:10 ORD
        10:58 SAN
        7Hrs, 48m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 05:10 - SAN 10:58 7h 48m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 05:10
        CLTCharlotte Airport 08:55
      • CLTCharlotte Airport 08:16
        SANSan Diego International Airport 10:58
      • 7h 48m (39m)
      • 1 Stop CLT · Charlotte 39m
      • American Airlines (AA 2842)Boeing 737 Max 8 Passenger
        American Airlines (AA 2275)Airbus
      • American Airlines (AA 2842)
        • M
        • -
        • W
        • T
        • F
        • S
        • S
      • 05:15 ORD
        11:07 SAN
        7Hrs, 52m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 05:15 - SAN 11:07 7h 52m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 05:15
        IAHHouston George Bush Intercontinental Airport 09:35
      • IAHHouston George Bush Intercontinental Airport 08:15
        SANSan Diego International Airport 11:07
      • 7h 52m (1h 20m)
      • 1 Stop IAH · Houston 1h 20m
      • United Airlines (UA 678)Boeing 757 300 Series
        United Airlines (UA 2491)Boeing 737 900
      • United Airlines (UA 678)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 05:20 MDW
        11:10 SAN
        7Hrs, 50m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:20 - SAN 11:10 7h 50m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:20
        DENDenver Intl Airport 09:45
      • DENDenver Intl Airport 06:55
        SANSan Diego International Airport 11:10
      • 7h 50m (2h 50m)
      • 1 Stop DEN · Denver 2h 50m
      • Southwest Airlines (WN 1376)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 673)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1376)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:25 MDW
        11:30 SAN
        8Hrs, 05m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:25 - SAN 11:30 8h 05m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:25
        DENDenver Intl Airport 10:00
      • DENDenver Intl Airport 07:00
        SANSan Diego International Airport 11:30
      • 8h 05m (3h)
      • 1 Stop DEN · Denver 3h
      • Southwest Airlines (WN 1929)Boeing 737 700
        Southwest Airlines (WN 673)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1929)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 05:30 MDW
        11:35 SAN
        8Hrs, 05m 1 Stop (BNA)
      • MDWChicago Midway Airport 05:30 - SAN 11:35 8h 05m 1 Stop (BNA) Nashville
      • MDWChicago Midway Airport 05:30
        BNANashville Airport 09:10
      • BNANashville Airport 06:55
        SANSan Diego International Airport 11:35
      • 8h 05m (2h 15m)
      • 1 Stop BNA · Nashville 2h 15m
      • Southwest Airlines (WN 367)Boeing 737 800
        Southwest Airlines (WN 1065)Boeing 737 800
      • Southwest Airlines (WN 367)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:30 MDW
        11:50 SAN
        8Hrs, 20m 1 Stop (DAL)
      • MDWChicago Midway Airport 05:30 - SAN 11:50 8h 20m 1 Stop (DAL)
      • MDWChicago Midway Airport 05:30
        DALDallas/Fort Worth Love Field Airport 10:35
      • DALDallas/Fort Worth Love Field Airport 07:50
        SANSan Diego International Airport 11:50
      • 8h 20m (2h 45m)
      • 1 Stop DAL · 2h 45m
      • Southwest Airlines (WN 472)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2197)Boeing 737 700
      • Southwest Airlines (WN 472)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:35 MDW
        09:15 SAN
        5Hrs, 40m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:35 - SAN 09:15 5h 40m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:35
        PHXPhoenix Sky Harbor Intl Airport 08:00
      • PHXPhoenix Sky Harbor Intl Airport 07:20
        SANSan Diego International Airport 09:15
      • 5h 40m (40m)
      • 1 Stop PHX · Phoenix 40m
      • Southwest Airlines (WN 2811)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1432)Boeing 737 700
      • Southwest Airlines (WN 2811)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:35 MDW
        10:25 SAN
        6Hrs, 50m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:35 - SAN 10:25 6h 50m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:35
        PHXPhoenix Sky Harbor Intl Airport 09:05
      • PHXPhoenix Sky Harbor Intl Airport 07:20
        SANSan Diego International Airport 10:25
      • 6h 50m (1h 45m)
      • 1 Stop PHX · Phoenix 1h 45m
      • Southwest Airlines (WN 2811)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1387)Boeing 737 700
      • Southwest Airlines (WN 2811)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:45 MDW
        09:45 SAN
        6Hrs, 00m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:45 - SAN 09:45 6h 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:45
        DENDenver Intl Airport 08:20
      • DENDenver Intl Airport 07:20
        SANSan Diego International Airport 09:45
      • 6h (1h)
      • 1 Stop DEN · Denver 1h
      • Southwest Airlines (WN 1376)Boeing 737 800
        Southwest Airlines (WN 1360)Boeing 737 800
      • Southwest Airlines (WN 1376)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:50 MDW
        11:55 SAN
        8Hrs, 05m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:50 - SAN 11:55 8h 05m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:50
        DENDenver Intl Airport 10:30
      • DENDenver Intl Airport 07:25
        SANSan Diego International Airport 11:55
      • 8h 05m (3h 05m)
      • 1 Stop DEN · Denver 3h 05m
      • Southwest Airlines (WN 1376)Boeing 737 800
        Southwest Airlines (WN 2120)Boeing 737 700
      • Southwest Airlines (WN 1376)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:55 MDW
        12:25 SAN
        8Hrs, 30m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:55 - SAN 12:25 8h 30m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:55
        PHXPhoenix Sky Harbor Intl Airport 11:15
      • PHXPhoenix Sky Harbor Intl Airport 07:40
        SANSan Diego International Airport 12:25
      • 8h 30m (3h 35m)
      • 1 Stop PHX · Phoenix 3h 35m
      • Southwest Airlines (WN 2811)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2799)Boeing 737 800
      • Southwest Airlines (WN 2811)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:55 MDW
        11:35 SAN
        7Hrs, 40m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:55 - SAN 11:35 7h 40m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:55
        PHXPhoenix Sky Harbor Intl Airport 10:15
      • PHXPhoenix Sky Harbor Intl Airport 07:40
        SANSan Diego International Airport 11:35
      • 7h 40m (2h 35m)
      • 1 Stop PHX · Phoenix 2h 35m
      • Southwest Airlines (WN 2811)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 3175)Boeing 737 700
      • Southwest Airlines (WN 2811)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:00 ORD
        12:01 SAN
        8Hrs, 01m 1 Stop (PHX)
      • ORDChicago O'Hare International Airport 06:00 - SAN 12:01 8h 01m 1 Stop (PHX) Phoenix
      • ORDChicago O'Hare International Airport 06:00
        PHXPhoenix Sky Harbor Intl Airport 10:40
      • PHXPhoenix Sky Harbor Intl Airport 07:55
        SANSan Diego International Airport 12:01
      • 8h 01m (2h 45m)
      • 1 Stop PHX · Phoenix 2h 45m
      • American Airlines (AA 319)Boeing 737 800
        American Airlines (AA 2122)Airbus
      • American Airlines (AA 319)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 06:00 ORD
        12:04 CLD
        8Hrs, 04m 1 Stop (PHX)
      • ORDChicago O'Hare International Airport 06:00 - CLD 12:04 8h 04m 1 Stop (PHX) Phoenix
      • ORDChicago O'Hare International Airport 06:00
        PHXPhoenix Sky Harbor Intl Airport 10:35
      • PHXPhoenix Sky Harbor Intl Airport 07:55
        CLDMcClellan-Palomar Airport 12:04
      • 8h 04m (2h 40m)
      • 1 Stop PHX · Phoenix 2h 40m
      • American Airlines (AA 319)Boeing 737 800
        American Airlines (AA 4204)Embraer Emb 175
      • American Airlines (AA 319)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 06:00 ORD
        13:00 SAN
        9Hrs, 00m 1 Stop (SEA)
      • ORDChicago O'Hare International Airport 06:00 - SAN 13:00 9h 1 Stop (SEA) Seattle
      • ORDChicago O'Hare International Airport 06:00
        SEASeattle/Tacoma International Airport 10:13
      • SEASeattle/Tacoma International Airport 08:30
        SANSan Diego International Airport 13:00
      • 9h (1h 43m)
      • 1 Stop SEA · Seattle 1h 43m
      • Alaska Airlines (AS 587)Boeing 737
        Alaska Airlines (AS 1108)Boeing 737 800
      • Alaska Airlines (AS 587)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • 06:00 ORD
        13:00 SAN
        9Hrs, 00m 1 Stop (SEA)
      • ORDChicago O'Hare International Airport 06:00 - SAN 13:00 9h 1 Stop (SEA) Seattle
      • ORDChicago O'Hare International Airport 06:00
        SEASeattle/Tacoma International Airport 10:13
      • SEASeattle/Tacoma International Airport 08:30
        SANSan Diego International Airport 13:00
      • 9h (1h 43m)
      • 1 Stop SEA · Seattle 1h 43m
      • Alaska Airlines (AS 587)Boeing 737
        Alaska Airlines (AS 1108)Boeing 737
      • Alaska Airlines (AS 587)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 06:00 ORD
        13:00 SAN
        9Hrs, 00m 1 Stop (SEA)
      • ORDChicago O'Hare International Airport 06:00 - SAN 13:00 9h 1 Stop (SEA) Seattle
      • ORDChicago O'Hare International Airport 06:00
        SEASeattle/Tacoma International Airport 10:13
      • SEASeattle/Tacoma International Airport 08:30
        SANSan Diego International Airport 13:00
      • 9h (1h 43m)
      • 1 Stop SEA · Seattle 1h 43m
      • Alaska Airlines (AS 587)Boeing 737
        Alaska Airlines (AS 1108)Boeing 737 Max 9 Passenger
      • Alaska Airlines (AS 587)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • 06:04 ORD
        12:34 SAN
        8Hrs, 30m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 06:04 - SAN 12:34 8h 30m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 06:04
        DCAWashington Ronald Reagan National Airport 09:59
      • DCAWashington Ronald Reagan National Airport 08:58
        SANSan Diego International Airport 12:34
      • 8h 30m (1h 01m)
      • 1 Stop DCA · Washington 1h 01m
      • American Airlines (AA 523)Boeing 737 800
        Alaska Airlines (AS 15)Boeing 737 800
      • American Airlines (AA 523)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 06:04 ORD
        12:39 SAN
        8Hrs, 35m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 06:04 - SAN 12:39 8h 35m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 06:04
        DCAWashington Ronald Reagan National Airport 09:59
      • DCAWashington Ronald Reagan National Airport 08:58
        SANSan Diego International Airport 12:39
      • 8h 35m (1h 01m)
      • 1 Stop DCA · Washington 1h 01m
      • American Airlines (AA 523)Boeing 737 800
        Alaska Airlines (AS 15)Boeing 737 800
      • American Airlines (AA 523)
        • -
        • T
        • W
        • T
        • F
        • S
        • S
      • 06:05 MDW
        12:10 SAN
        8Hrs, 05m 1 Stop (LAS)
      • MDWChicago Midway Airport 06:05 - SAN 12:10 8h 05m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 06:05
        LASLas Vegas McCarran International Airport 10:55
      • LASLas Vegas McCarran International Airport 08:00
        SANSan Diego International Airport 12:10
      • 8h 05m (2h 55m)
      • 1 Stop LAS · Las Vegas 2h 55m
      • Southwest Airlines (WN 1978)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2118)Boeing 737 700
      • Southwest Airlines (WN 1978)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:05 MDW
        12:25 SAN
        8Hrs, 20m 1 Stop (LAS)
      • MDWChicago Midway Airport 06:05 - SAN 12:25 8h 20m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 06:05
        LASLas Vegas McCarran International Airport 11:10
      • LASLas Vegas McCarran International Airport 08:00
        SANSan Diego International Airport 12:25
      • 8h 20m (3h 10m)
      • 1 Stop LAS · Las Vegas 3h 10m
      • Southwest Airlines (WN 1978)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1729)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1978)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:05 MDW
        10:25 SAN
        6Hrs, 20m 1 Stop (LAS)
      • MDWChicago Midway Airport 06:05 - SAN 10:25 6h 20m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 06:05
        LASLas Vegas McCarran International Airport 09:10
      • LASLas Vegas McCarran International Airport 08:00
        SANSan Diego International Airport 10:25
      • 6h 20m (1h 10m)
      • 1 Stop LAS · Las Vegas 1h 10m
      • Southwest Airlines (WN 1978)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1428)Boeing 737 800
      • Southwest Airlines (WN 1978)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:05 MDW
        11:15 SAN
        7Hrs, 10m 1 Stop (LAS)
      • MDWChicago Midway Airport 06:05 - SAN 11:15 7h 10m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 06:05
        LASLas Vegas McCarran International Airport 10:00
      • LASLas Vegas McCarran International Airport 08:00
        SANSan Diego International Airport 11:15
      • 7h 10m (2h)
      • 1 Stop LAS · Las Vegas 2h
      • Southwest Airlines (WN 1978)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2118)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1978)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:15 ORD
        10:25 SAN
        6Hrs, 10m 1 Stop (LAS)
      • ORDChicago O'Hare International Airport 06:15 - SAN 10:25 6h 10m 1 Stop (LAS) Las Vegas
      • ORDChicago O'Hare International Airport 06:15
        LASLas Vegas McCarran International Airport 09:10
      • LASLas Vegas McCarran International Airport 08:10
        SANSan Diego International Airport 10:25
      • 6h 10m (1h)
      • 1 Stop LAS · Las Vegas 1h
      • Southwest Airlines (WN 1749)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1428)Boeing 737 800
      • Southwest Airlines (WN 1749)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:15 ORD
        10:50 SAN
        6Hrs, 35m 1 Stop (LAS)
      • ORDChicago O'Hare International Airport 06:15 - SAN 10:50 6h 35m 1 Stop (LAS) Las Vegas
      • ORDChicago O'Hare International Airport 06:15
        LASLas Vegas McCarran International Airport 09:35
      • LASLas Vegas McCarran International Airport 08:10
        SANSan Diego International Airport 10:50
      • 6h 35m (1h 25m)
      • 1 Stop LAS · Las Vegas 1h 25m
      • Southwest Airlines (WN 1749)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 5830)Boeing 737 700
      • Southwest Airlines (WN 1749)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 06:15 ORD
        11:15 SAN
        7Hrs, 00m 1 Stop (LAS)
      • ORDChicago O'Hare International Airport 06:15 - SAN 11:15 7h 1 Stop (LAS) Las Vegas
      • ORDChicago O'Hare International Airport 06:15
        LASLas Vegas McCarran International Airport 10:00
      • LASLas Vegas McCarran International Airport 08:10
        SANSan Diego International Airport 11:15
      • 7h (1h 50m)
      • 1 Stop LAS · Las Vegas 1h 50m
      • Southwest Airlines (WN 1749)Boeing 737 800
        Southwest Airlines (WN 2118)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1749)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:15 ORD
        11:40 SAN
        7Hrs, 25m 1 Stop (LAS)
      • ORDChicago O'Hare International Airport 06:15 - SAN 11:40 7h 25m 1 Stop (LAS) Las Vegas
      • ORDChicago O'Hare International Airport 06:15
        LASLas Vegas McCarran International Airport 10:25
      • LASLas Vegas McCarran International Airport 08:10
        SANSan Diego International Airport 11:40
      • 7h 25m (2h 15m)
      • 1 Stop LAS · Las Vegas 2h 15m
      • Southwest Airlines (WN 1749)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1056)Boeing 737 700
      • Southwest Airlines (WN 1749)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:15 ORD
        12:10 SAN
        7Hrs, 55m 1 Stop (LAS)
      • ORDChicago O'Hare International Airport 06:15 - SAN 12:10 7h 55m 1 Stop (LAS) Las Vegas
      • ORDChicago O'Hare International Airport 06:15
        LASLas Vegas McCarran International Airport 10:55
      • LASLas Vegas McCarran International Airport 08:10
        SANSan Diego International Airport 12:10
      • 7h 55m (2h 45m)
      • 1 Stop LAS · Las Vegas 2h 45m
      • Southwest Airlines (WN 1749)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2118)Boeing 737 700
      • Southwest Airlines (WN 1749)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:15 ORD
        12:25 SAN
        8Hrs, 10m 1 Stop (LAS)
      • ORDChicago O'Hare International Airport 06:15 - SAN 12:25 8h 10m 1 Stop (LAS) Las Vegas
      • ORDChicago O'Hare International Airport 06:15
        LASLas Vegas McCarran International Airport 11:10
      • LASLas Vegas McCarran International Airport 08:10
        SANSan Diego International Airport 12:25
      • 8h 10m (3h)
      • 1 Stop LAS · Las Vegas 3h
      • Southwest Airlines (WN 1749)Boeing 737 800
        Southwest Airlines (WN 1729)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1749)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:15 ORD
        13:00 SAN
        8Hrs, 45m 1 Stop (LAS)
      • ORDChicago O'Hare International Airport 06:15 - SAN 13:00 8h 45m 1 Stop (LAS) Las Vegas
      • ORDChicago O'Hare International Airport 06:15
        LASLas Vegas McCarran International Airport 11:45
      • LASLas Vegas McCarran International Airport 08:10
        SANSan Diego International Airport 13:00
      • 8h 45m (3h 35m)
      • 1 Stop LAS · Las Vegas 3h 35m
      • Southwest Airlines (WN 1749)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2118)Boeing 737 800
      • Southwest Airlines (WN 1749)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:20 MDW
        12:25 SAN
        8Hrs, 05m 1 Stop (BWI)
      • MDWChicago Midway Airport 06:20 - SAN 12:25 8h 05m 1 Stop (BWI) Baltimore
      • MDWChicago Midway Airport 06:20
        BWIBaltimore Washington International Airport 09:50
      • BWIBaltimore Washington International Airport 09:05
        SANSan Diego International Airport 12:25
      • 8h 05m (45m)
      • 1 Stop BWI · Baltimore 45m
      • Southwest Airlines (WN 3299)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1351)Boeing 737 700
      • Southwest Airlines (WN 3299)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:30 ORD
        12:41 SAN
        8Hrs, 11m 1 Stop (SFO)
      • ORDChicago O'Hare International Airport 06:30 - SAN 12:41 8h 11m 1 Stop (SFO) San Francisco
      • ORDChicago O'Hare International Airport 06:30
        SFOSan Francisco International Airport 10:57
      • SFOSan Francisco International Airport 09:20
        SANSan Diego International Airport 12:41
      • 8h 11m (1h 37m)
      • 1 Stop SFO · San Francisco 1h 37m
      • United Airlines (UA 336)Boeing 757 300 Series
        United Airlines (UA 1095)Boeing 737 Max 8 Passenger
      • United Airlines (UA 336)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 06:35 MDW
        10:30 SAN
        5Hrs, 55m 1 Stop (STL)
      • MDWChicago Midway Airport 06:35 - SAN 10:30 5h 55m 1 Stop (STL) Saint Louis
      • MDWChicago Midway Airport 06:35
        STLSt Louis Lambert Intl Airport 08:35
      • STLSt Louis Lambert Intl Airport 07:45
        SANSan Diego International Airport 10:30
      • 5h 55m (50m)
      • 1 Stop STL · Saint Louis 50m
      • Southwest Airlines (WN 1045)Boeing 737 800
        Southwest Airlines (WN 2996)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1045)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:40 ORD
        11:29 SAN
        6Hrs, 49m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 06:40 - SAN 11:29 6h 49m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 06:40
        DENDenver Intl Airport 10:05
      • DENDenver Intl Airport 08:34
        SANSan Diego International Airport 11:29
      • 6h 49m (1h 31m)
      • 1 Stop DEN · Denver 1h 31m
      • Frontier Airlines (F9 3173)Airbus A321 Neo
        Frontier Airlines (F9 4927)Airbus A320 Neo
      • Frontier Airlines (F9 3173)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 06:45 MDW
        11:25 SAN
        6Hrs, 40m 1 Stop (MCI)
      • MDWChicago Midway Airport 06:45 - SAN 11:25 6h 40m 1 Stop (MCI) Kansas City
      • MDWChicago Midway Airport 06:45
        MCIKansas City International Airport 10:00
      • MCIKansas City International Airport 08:10
        SANSan Diego International Airport 11:25
      • 6h 40m (1h 50m)
      • 1 Stop MCI · Kansas City 1h 50m
      • Southwest Airlines (WN 4013)Boeing 737 700
        Southwest Airlines (WN 1062)Boeing 737 700
      • Southwest Airlines (WN 4013)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:45 MDW
        11:29 SAN
        6Hrs, 44m 1 Stop (DEN)
      • MDWChicago Midway Airport 06:45 - SAN 11:29 6h 44m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 06:45
        DENDenver Intl Airport 10:05
      • DENDenver Intl Airport 08:35
        SANSan Diego International Airport 11:29
      • 6h 44m (1h 30m)
      • 1 Stop DEN · Denver 1h 30m
      • Frontier Airlines (F9 2209)Airbus A320 Neo
        Frontier Airlines (F9 4927)Airbus A320 Neo
      • Frontier Airlines (F9 2209)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 06:45 MDW
        11:30 SAN
        6Hrs, 45m 1 Stop (MCI)
      • MDWChicago Midway Airport 06:45 - SAN 11:30 6h 45m 1 Stop (MCI) Kansas City
      • MDWChicago Midway Airport 06:45
        MCIKansas City International Airport 10:05
      • MCIKansas City International Airport 08:10
        SANSan Diego International Airport 11:30
      • 6h 45m (1h 55m)
      • 1 Stop MCI · Kansas City 1h 55m
      • Southwest Airlines (WN 4013)Boeing 737 700
        Southwest Airlines (WN 2281)Boeing 737 700
      • Southwest Airlines (WN 4013)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 10:30 DEN
        08:10 MCI
        7Hrs, 10m 1 Stop (SAN)
      • DENDenver Intl Airport 10:30 - MCI 08:10 7h 10m 1 Stop (SAN) San Diego
      • DENDenver Intl Airport 10:30
        MDWChicago Midway Airport 06:45
      • SANSan Diego International Airport 11:55
        MCIKansas City International Airport 08:10
      • 7h 10m (1h 30m)
      • 1 Stop SAN · San Diego 1h 30m
      • Southwest Airlines (WN 2120)Boeing 737 700
        Southwest Airlines (WN 4013)Boeing 737 700
      • Southwest Airlines (WN 2120)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:45 MDW
        12:06 SAN
        7Hrs, 21m 1 Stop (DEN)
      • MDWChicago Midway Airport 06:45 - SAN 12:06 7h 21m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 06:45
        DENDenver Intl Airport 10:42
      • DENDenver Intl Airport 08:35
        SANSan Diego International Airport 12:06
      • 7h 21m (2h 07m)
      • 1 Stop DEN · Denver 2h 07m
      • Frontier Airlines (F9 2209)Airbus A320 Neo
        Frontier Airlines (F9 2421)Airbus A320 Neo
      • Frontier Airlines (F9 2209)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 06:55 ORD
        12:51 SAN
        7Hrs, 56m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 06:55 - SAN 12:51 7h 56m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 06:55
        DFWDallas/Fort Worth Intl Airport 11:42
      • DFWDallas/Fort Worth Intl Airport 09:35
        SANSan Diego International Airport 12:51
      • 7h 56m (2h 07m)
      • 1 Stop DFW · Dallas 2h 07m
      • American Airlines (AA 1555)Boeing 737 800
        American Airlines (AA 2784)Airbus
      • American Airlines (AA 1555)
        • M
        • T
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      • 07:00 MDW
        12:55 SAN
        7Hrs, 55m 1 Stop (PHX)
      • MDWChicago Midway Airport 07:00 - SAN 12:55 7h 55m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 07:00
        PHXPhoenix Sky Harbor Intl Airport 11:45
      • PHXPhoenix Sky Harbor Intl Airport 08:45
        SANSan Diego International Airport 12:55
      • 7h 55m (3h)
      • 1 Stop PHX · Phoenix 3h
      • Southwest Airlines (WN 840)Boeing 737 700
        Southwest Airlines (WN 1762)Boeing 737 700
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      What’s the fastest flight time from Chicago to San Diego?

      The fastest flight time for direct flights from Chicago to San Diego is 4 hours 15 minutes. Check latest flight schedules & prices on Wego.

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

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

      How far is San Diego from Chicago?

      The flight distance between Chicago and San Diego is 2787km. 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 Chicago to San Diego?

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

      Popular Airlines Flying From Chicago to San Diego

      American Airlines ‏()

      Popular Destinations From San Diego

      Popular Destinations From Chicago

      Popular Hotels in San Diego

      Hotels In Popular Destinations