Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Frontier Airlines

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

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

Travel Period: December 2024 - November 2025

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

  • 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 San Diego 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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      • Availability
        • M
        • T
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        • T
        • F
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        • S
      • 16:30 SAN
        01:00 MDW
        6Hrs, 30m Direct
      • SANSan Diego International Airport 16:30 - MDW 01:00 6h 30m Direct
      • SANSan Diego International Airport 16:30
      • MDWChicago Midway Airport 01:00
      • 6h 30m
      • Direct
      • Southwest Airlines (WN 2053)Boeing 737 700
      • Southwest Airlines (WN 2053)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 16:40 SAN
        22:45 ORD
        4Hrs, 05m Direct
      • SANSan Diego International Airport 16:40 - ORD 22:45 4h 05m Direct
      • SANSan Diego International Airport 16:40
      • ORDChicago O'Hare International Airport 22:45
      • 4h 05m
      • Direct
      • United Airlines (UA 2486)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2486)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 16:40 SAN
        22:45 ORD
        4Hrs, 05m Direct
      • SANSan Diego International Airport 16:40 - ORD 22:45 4h 05m Direct
      • SANSan Diego International Airport 16:40
      • ORDChicago O'Hare International Airport 22:45
      • 4h 05m
      • Direct
      • United Airlines (UA 2486)Boeing 737 800
      • United Airlines (UA 2486)
        • -
        • -
        • W
        • -
        • F
        • S
        • S
      • Boeing 737 800
      • 16:40 SAN
        22:45 ORD
        4Hrs, 05m Direct
      • SANSan Diego International Airport 16:40 - ORD 22:45 4h 05m Direct
      • SANSan Diego International Airport 16:40
      • ORDChicago O'Hare International Airport 22:45
      • 4h 05m
      • Direct
      • United Airlines (UA 2486)Boeing 737 900
      • United Airlines (UA 2486)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 900
      • 16:45 SAN
        22:35 MDW
        3Hrs, 50m Direct
      • SANSan Diego International Airport 16:45 - MDW 22:35 3h 50m Direct
      • SANSan Diego International Airport 16:45
      • MDWChicago Midway Airport 22:35
      • 3h 50m
      • Direct
      • Southwest Airlines (WN 1170)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1170)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 16:50 SAN
        22:40 MDW
        3Hrs, 50m Direct
      • SANSan Diego International Airport 16:50 - MDW 22:40 3h 50m Direct
      • SANSan Diego International Airport 16:50
      • MDWChicago Midway Airport 22:40
      • 3h 50m
      • Direct
      • Southwest Airlines (WN 1506)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1506)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 17:30 SAN
        01:05 MDW
        5Hrs, 35m Direct
      • SANSan Diego International Airport 17:30 - MDW 01:05 5h 35m Direct
      • SANSan Diego International Airport 17:30
      • MDWChicago Midway Airport 01:05
      • 5h 35m
      • Direct
      • Southwest Airlines (WN 2308)Boeing 737 700
      • Southwest Airlines (WN 2308)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 18:55 SAN
        00:50 MDW
        3Hrs, 55m Direct
      • SANSan Diego International Airport 18:55 - MDW 00:50 3h 55m Direct
      • SANSan Diego International Airport 18:55
      • MDWChicago Midway Airport 00:50
      • 3h 55m
      • Direct
      • Southwest Airlines (WN 2316)Boeing 737 700
      • Southwest Airlines (WN 2316)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 18:55 SAN
        00:50 MDW
        3Hrs, 55m Direct
      • SANSan Diego International Airport 18:55 - MDW 00:50 3h 55m Direct
      • SANSan Diego International Airport 18:55
      • MDWChicago Midway Airport 00:50
      • 3h 55m
      • Direct
      • Southwest Airlines (WN 1376)Boeing 737 800
      • Southwest Airlines (WN 1376)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 800
      • 18:55 SAN
        00:50 MDW
        3Hrs, 55m Direct
      • SANSan Diego International Airport 18:55 - MDW 00:50 3h 55m Direct
      • SANSan Diego International Airport 18:55
      • MDWChicago Midway Airport 00:50
      • 3h 55m
      • Direct
      • Southwest Airlines (WN 2533)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2533)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 22:30 SAN
        04:35 ORD
        4Hrs, 05m Direct
      • SANSan Diego International Airport 22:30 - ORD 04:35 4h 05m Direct
      • SANSan Diego International Airport 22:30
      • ORDChicago O'Hare International Airport 04:35
      • 4h 05m
      • Direct
      • United Airlines (UA 2352)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2352)
        • M
        • T
        • W
        • -
        • F
        • S
        • S
      • Boeing 737 Max 8 Passenger
      • 22:30 SAN
        04:35 ORD
        4Hrs, 05m Direct
      • SANSan Diego International Airport 22:30 - ORD 04:35 4h 05m Direct
      • SANSan Diego International Airport 22:30
      • ORDChicago O'Hare International Airport 04:35
      • 4h 05m
      • Direct
      • United Airlines (UA 2352)Boeing 737 800
      • United Airlines (UA 2352)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 800
      • 22:39 SAN
        04:43 ORD
        4Hrs, 04m Direct
      • SANSan Diego International Airport 22:39 - ORD 04:43 4h 04m Direct
      • SANSan Diego International Airport 22:39
      • ORDChicago O'Hare International Airport 04:43
      • 4h 04m
      • Direct
      • American Airlines (AA 2985)Airbus
      • American Airlines (AA 2985)
        • M
        • T
        • W
        • -
        • F
        • S
        • S
      • Airbus
      • 06:15 SAN
        12:26 ORD
        4Hrs, 11m Direct
      • SANSan Diego International Airport 06:15 - ORD 12:26 4h 11m Direct
      • SANSan Diego International Airport 06:15
      • ORDChicago O'Hare International Airport 12:26
      • 4h 11m
      • Direct
      • American Airlines (AA 518)Airbus
      • American Airlines (AA 518)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Airbus
      • 06:20 SAN
        12:20 MDW
        4Hrs, 00m Direct
      • SANSan Diego International Airport 06:20 - MDW 12:20 4h Direct
      • SANSan Diego International Airport 06:20
      • MDWChicago Midway Airport 12:20
      • 4h
      • Direct
      • Southwest Airlines (WN 770)Boeing 737 700
      • Southwest Airlines (WN 770)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 06:25 SAN
        12:25 MDW
        4Hrs, 00m Direct
      • SANSan Diego International Airport 06:25 - MDW 12:25 4h Direct
      • SANSan Diego International Airport 06:25
      • MDWChicago Midway Airport 12:25
      • 4h
      • Direct
      • Southwest Airlines (WN 770)Boeing 737 700
      • Southwest Airlines (WN 770)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Boeing 737 700
      • 06:30 SAN
        12:30 MDW
        4Hrs, 00m Direct
      • SANSan Diego International Airport 06:30 - MDW 12:30 4h Direct
      • SANSan Diego International Airport 06:30
      • MDWChicago Midway Airport 12:30
      • 4h
      • Direct
      • Southwest Airlines (WN 770)Boeing 737 700
      • Southwest Airlines (WN 770)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 700
      • 07:00 SAN
        13:09 ORD
        4Hrs, 09m Direct
      • SANSan Diego International Airport 07:00 - ORD 13:09 4h 09m Direct
      • SANSan Diego International Airport 07:00
      • ORDChicago O'Hare International Airport 13:09
      • 4h 09m
      • Direct
      • United Airlines (UA 1502)Boeing 737 900
      • United Airlines (UA 1502)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 900
      • 07:00 SAN
        12:55 MDW
        3Hrs, 55m Direct
      • SANSan Diego International Airport 07:00 - MDW 12:55 3h 55m Direct
      • SANSan Diego International Airport 07:00
      • MDWChicago Midway Airport 12:55
      • 3h 55m
      • Direct
      • Southwest Airlines (WN 770)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 770)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 07:00 SAN
        13:09 ORD
        4Hrs, 09m Direct
      • SANSan Diego International Airport 07:00 - ORD 13:09 4h 09m Direct
      • SANSan Diego International Airport 07:00
      • ORDChicago O'Hare International Airport 13:09
      • 4h 09m
      • Direct
      • United Airlines (UA 1502)Airbus A321 Neo
      • United Airlines (UA 1502)
        • -
        • T
        • W
        • -
        • -
        • S
        • S
      • Airbus A321 Neo
      • 07:30 SAN
        13:25 MDW
        3Hrs, 55m Direct
      • SANSan Diego International Airport 07:30 - MDW 13:25 3h 55m Direct
      • SANSan Diego International Airport 07:30
      • MDWChicago Midway Airport 13:25
      • 3h 55m
      • Direct
      • Southwest Airlines (WN 770)Boeing 737 800
      • Southwest Airlines (WN 770)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 08:15 SAN
        16:35 MDW
        6Hrs, 20m Direct
      • SANSan Diego International Airport 08:15 - MDW 16:35 6h 20m Direct
      • SANSan Diego International Airport 08:15
      • MDWChicago Midway Airport 16:35
      • 6h 20m
      • Direct
      • Southwest Airlines (WN 2777)Boeing 737 700
      • Southwest Airlines (WN 2777)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 09:00 SAN
        14:55 MDW
        3Hrs, 55m Direct
      • SANSan Diego International Airport 09:00 - MDW 14:55 3h 55m Direct
      • SANSan Diego International Airport 09:00
      • MDWChicago Midway Airport 14:55
      • 3h 55m
      • Direct
      • Southwest Airlines (WN 1444)Boeing 737 700
      • Southwest Airlines (WN 1444)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 09:05 SAN
        18:15 MDW
        7Hrs, 10m Direct
      • SANSan Diego International Airport 09:05 - MDW 18:15 7h 10m Direct
      • SANSan Diego International Airport 09:05
      • MDWChicago Midway Airport 18:15
      • 7h 10m
      • Direct
      • Southwest Airlines (WN 3427)Boeing 737 700
      • Southwest Airlines (WN 3427)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 10:00 SAN
        00:59 ORD
        12Hrs, 59m Direct
      • SANSan Diego International Airport 10:00 - ORD 00:59 12h 59m Direct
      • SANSan Diego International Airport 10:00
      • ORDChicago O'Hare International Airport 00:59
      • 12h 59m
      • Direct
      • United Airlines (UA 2484)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2484)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 10:00 SAN
        00:59 ORD
        12Hrs, 59m Direct
      • SANSan Diego International Airport 10:00 - ORD 00:59 12h 59m Direct
      • SANSan Diego International Airport 10:00
      • ORDChicago O'Hare International Airport 00:59
      • 12h 59m
      • Direct
      • United Airlines (UA 2484)Boeing 737 800
      • United Airlines (UA 2484)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 800
      • 10:30 SAN
        16:39 ORD
        4Hrs, 09m Direct
      • SANSan Diego International Airport 10:30 - ORD 16:39 4h 09m Direct
      • SANSan Diego International Airport 10:30
      • ORDChicago O'Hare International Airport 16:39
      • 4h 09m
      • Direct
      • United Airlines (UA 714)Airbus A321 Neo
      • United Airlines (UA 714)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Airbus A321 Neo
      • 10:57 SAN
        17:06 ORD
        4Hrs, 09m Direct
      • SANSan Diego International Airport 10:57 - ORD 17:06 4h 09m Direct
      • SANSan Diego International Airport 10:57
      • ORDChicago O'Hare International Airport 17:06
      • 4h 09m
      • Direct
      • United Airlines (UA 714)Airbus A321 Neo
      • United Airlines (UA 714)
        • -
        • -
        • W
        • T
        • -
        • -
        • S
      • Airbus A321 Neo
      • 10:57 SAN
        17:06 ORD
        4Hrs, 09m Direct
      • SANSan Diego International Airport 10:57 - ORD 17:06 4h 09m Direct
      • SANSan Diego International Airport 10:57
      • ORDChicago O'Hare International Airport 17:06
      • 4h 09m
      • Direct
      • United Airlines (UA 714)Boeing 737 900
      • United Airlines (UA 714)
        • M
        • T
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 900
      • 11:15 SAN
        17:10 MDW
        3Hrs, 55m Direct
      • SANSan Diego International Airport 11:15 - MDW 17:10 3h 55m Direct
      • SANSan Diego International Airport 11:15
      • MDWChicago Midway Airport 17:10
      • 3h 55m
      • Direct
      • Southwest Airlines (WN 3002)Boeing 737 700
      • Southwest Airlines (WN 3002)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 700
      • 11:35 SAN
        19:25 MDW
        5Hrs, 50m Direct
      • SANSan Diego International Airport 11:35 - MDW 19:25 5h 50m Direct
      • SANSan Diego International Airport 11:35
      • MDWChicago Midway Airport 19:25
      • 5h 50m
      • Direct
      • Southwest Airlines (WN 1471)Boeing 737 800
      • Southwest Airlines (WN 1471)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 800
      • 12:46 SAN
        18:55 ORD
        4Hrs, 09m Direct
      • SANSan Diego International Airport 12:46 - ORD 18:55 4h 09m Direct
      • SANSan Diego International Airport 12:46
      • ORDChicago O'Hare International Airport 18:55
      • 4h 09m
      • Direct
      • United Airlines (UA 349)Boeing 737 900
      • United Airlines (UA 349)
        • M
        • -
        • W
        • -
        • -
        • -
        • S
      • Boeing 737 900
      • 12:46 SAN
        18:55 ORD
        4Hrs, 09m Direct
      • SANSan Diego International Airport 12:46 - ORD 18:55 4h 09m Direct
      • SANSan Diego International Airport 12:46
      • ORDChicago O'Hare International Airport 18:55
      • 4h 09m
      • Direct
      • United Airlines (UA 349)Airbus A321 Neo
      • United Airlines (UA 349)
        • -
        • T
        • -
        • -
        • F
        • S
        • -
      • Airbus A321 Neo
      • 12:50 SAN
        23:20 ORD
        8Hrs, 30m Direct
      • SANSan Diego International Airport 12:50 - ORD 23:20 8h 30m Direct
      • SANSan Diego International Airport 12:50
      • ORDChicago O'Hare International Airport 23:20
      • 8h 30m
      • Direct
      • United Airlines (UA 1738)Boeing 737 Max 8 Passenger
      • United Airlines (UA 1738)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • Boeing 737 Max 8 Passenger
      • 12:50 SAN
        23:20 ORD
        8Hrs, 30m Direct
      • SANSan Diego International Airport 12:50 - ORD 23:20 8h 30m Direct
      • SANSan Diego International Airport 12:50
      • ORDChicago O'Hare International Airport 23:20
      • 8h 30m
      • Direct
      • United Airlines (UA 1738)Boeing 737 900
      • United Airlines (UA 1738)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 900
      • 12:50 SAN
        23:20 ORD
        8Hrs, 30m Direct
      • SANSan Diego International Airport 12:50 - ORD 23:20 8h 30m Direct
      • SANSan Diego International Airport 12:50
      • ORDChicago O'Hare International Airport 23:20
      • 8h 30m
      • Direct
      • United Airlines (UA 1738)Boeing 737 800
      • United Airlines (UA 1738)
        • M
        • -
        • W
        • -
        • F
        • -
        • -
      • Boeing 737 800
      • 13:10 SAN
        19:10 MDW
        4Hrs, 00m Direct
      • SANSan Diego International Airport 13:10 - MDW 19:10 4h Direct
      • SANSan Diego International Airport 13:10
      • MDWChicago Midway Airport 19:10
      • 4h
      • Direct
      • Southwest Airlines (WN 2138)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2138)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 13:28 SAN
        19:35 ORD
        4Hrs, 07m Direct
      • SANSan Diego International Airport 13:28 - ORD 19:35 4h 07m Direct
      • SANSan Diego International Airport 13:28
      • ORDChicago O'Hare International Airport 19:35
      • 4h 07m
      • Direct
      • American Airlines (AA 2131)Boeing 737 800
      • American Airlines (AA 2131)
        • M
        • T
        • W
        • -
        • -
        • S
        • S
      • Boeing 737 800
      • 13:45 SAN
        19:40 MDW
        3Hrs, 55m Direct
      • SANSan Diego International Airport 13:45 - MDW 19:40 3h 55m Direct
      • SANSan Diego International Airport 13:45
      • MDWChicago Midway Airport 19:40
      • 3h 55m
      • Direct
      • Southwest Airlines (WN 391)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 391)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 15:25 SAN
        23:59 ORD
        6Hrs, 34m Direct
      • SANSan Diego International Airport 15:25 - ORD 23:59 6h 34m Direct
      • SANSan Diego International Airport 15:25
      • ORDChicago O'Hare International Airport 23:59
      • 6h 34m
      • Direct
      • United Airlines (UA 556)Boeing 737 900
      • United Airlines (UA 556)
        • M
        • T
        • W
        • -
        • F
        • S
        • S
      • Boeing 737 900
      • 15:40 SAN
        23:05 ORD
        5Hrs, 25m Direct
      • SANSan Diego International Airport 15:40 - ORD 23:05 5h 25m Direct
      • SANSan Diego International Airport 15:40
      • ORDChicago O'Hare International Airport 23:05
      • 5h 25m
      • Direct
      • Southwest Airlines (WN 3970)Boeing 737 700
      • Southwest Airlines (WN 3970)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Boeing 737 700
      • 15:45 SAN
        21:35 MDW
        3Hrs, 50m Direct
      • SANSan Diego International Airport 15:45 - MDW 21:35 3h 50m Direct
      • SANSan Diego International Airport 15:45
      • MDWChicago Midway Airport 21:35
      • 3h 50m
      • Direct
      • Southwest Airlines (WN 4042)Boeing 737 800
      • Southwest Airlines (WN 4042)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 16:05 SAN
        23:30 MDW
        5Hrs, 25m 1 Stop (DEN)
      • SANSan Diego International Airport 16:05 - MDW 23:30 5h 25m 1 Stop (DEN) Denver
      • SANSan Diego International Airport 16:05
        DENDenver Intl Airport 20:15
      • DENDenver Intl Airport 19:25
        MDWChicago Midway Airport 23:30
      • 5h 25m (50m)
      • 1 Stop DEN · Denver 50m
      • Southwest Airlines (WN 1199)Boeing 737 800
        Southwest Airlines (WN 4514)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1199)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 16:05 SAN
        23:40 ORD
        5Hrs, 35m 1 Stop (PHX)
      • SANSan Diego International Airport 16:05 - ORD 23:40 5h 35m 1 Stop (PHX) Phoenix
      • SANSan Diego International Airport 16:05
        PHXPhoenix Sky Harbor Intl Airport 19:10
      • PHXPhoenix Sky Harbor Intl Airport 18:25
        ORDChicago O'Hare International Airport 23:40
      • 5h 35m (45m)
      • 1 Stop PHX · Phoenix 45m
      • Southwest Airlines (WN 3650)Boeing 737 700
        Southwest Airlines (WN 3970)Boeing 737 800
      • Southwest Airlines (WN 3650)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 16:05 SAN
        00:10 MDW
        6Hrs, 05m 1 Stop (PHX)
      • SANSan Diego International Airport 16:05 - MDW 00:10 6h 05m 1 Stop (PHX) Phoenix
      • SANSan Diego International Airport 16:05
        PHXPhoenix Sky Harbor Intl Airport 19:55
      • PHXPhoenix Sky Harbor Intl Airport 18:25
        MDWChicago Midway Airport 00:10
      • 6h 05m (1h 30m)
      • 1 Stop PHX · Phoenix 1h 30m
      • Southwest Airlines (WN 3650)Boeing 737 700
        Southwest Airlines (WN 1651)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3650)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 16:09 SAN
        23:57 ORD
        5Hrs, 48m 1 Stop (DEN)
      • SANSan Diego International Airport 16:09 - ORD 23:57 5h 48m 1 Stop (DEN) Denver
      • SANSan Diego International Airport 16:09
        DENDenver Intl Airport 20:25
      • DENDenver Intl Airport 19:37
        ORDChicago O'Hare International Airport 23:57
      • 5h 48m (48m)
      • 1 Stop DEN · Denver 48m
      • United Airlines (UA 682)Boeing 737 800
        United Airlines (UA 377)Boeing 737 900
      • United Airlines (UA 682)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 16:10 SAN
        00:52 ORD
        6Hrs, 42m 1 Stop (SFO)
      • SANSan Diego International Airport 16:10 - ORD 00:52 6h 42m 1 Stop (SFO) San Francisco
      • SANSan Diego International Airport 16:10
        SFOSan Francisco International Airport 18:35
      • SFOSan Francisco International Airport 17:49
        ORDChicago O'Hare International Airport 00:52
      • 6h 42m (46m)
      • 1 Stop SFO · San Francisco 46m
      • United Airlines (UA 2117)Boeing 737 Max 8 Passenger
        United Airlines (UA 737)Airbus A321 Neo
      • United Airlines (UA 2117)
        • -
        • T
        • W
        • -
        • -
        • S
        • S
      • 16:30 SAN
        00:15 MDW
        5Hrs, 45m 1 Stop (DEN)
      • SANSan Diego International Airport 16:30 - MDW 00:15 5h 45m 1 Stop (DEN) Denver
      • SANSan Diego International Airport 16:30
        DENDenver Intl Airport 20:55
      • DENDenver Intl Airport 19:50
        MDWChicago Midway Airport 00:15
      • 5h 45m (1h 05m)
      • 1 Stop DEN · Denver 1h 05m
      • Southwest Airlines (WN 2817)Boeing 737 800
        Southwest Airlines (WN 3078)Boeing 737 800
      • Southwest Airlines (WN 2817)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 16:30 SAN
        00:20 MDW
        5Hrs, 50m 1 Stop (DAL)
      • SANSan Diego International Airport 16:30 - MDW 00:20 5h 50m 1 Stop (DAL) Dallas
      • SANSan Diego International Airport 16:30
        DALDallas/Fort Worth Love Field Airport 22:15
      • DALDallas/Fort Worth Love Field Airport 21:20
        MDWChicago Midway Airport 00:20
      • 5h 50m (55m)
      • 1 Stop DAL · Dallas 55m
      • Southwest Airlines (WN 4588)Boeing 737 700
        Southwest Airlines (WN 54)Boeing 737 700
      • Southwest Airlines (WN 4588)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 16:30 SAN
        01:15 MDW
        6Hrs, 45m 1 Stop (LAS)
      • SANSan Diego International Airport 16:30 - MDW 01:15 6h 45m 1 Stop (LAS) Las Vegas
      • SANSan Diego International Airport 16:30
        LASLas Vegas McCarran International Airport 19:50
      • LASLas Vegas McCarran International Airport 17:50
        MDWChicago Midway Airport 01:15
      • 6h 45m (2h)
      • 1 Stop LAS · Las Vegas 2h
      • Southwest Airlines (WN 1425)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 3242)Boeing 737 700
      • Southwest Airlines (WN 1425)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 16:35 SAN
        00:20 ORD
        5Hrs, 45m 1 Stop (PHX)
      • SANSan Diego International Airport 16:35 - ORD 00:20 5h 45m 1 Stop (PHX) Phoenix
      • SANSan Diego International Airport 16:35
        PHXPhoenix Sky Harbor Intl Airport 19:50
      • PHXPhoenix Sky Harbor Intl Airport 18:58
        ORDChicago O'Hare International Airport 00:20
      • 5h 45m (52m)
      • 1 Stop PHX · Phoenix 52m
      • American Airlines (AA 1951)Boeing 737 Max 8 Passenger
        American Airlines (AA 630)Boeing 737 800
      • American Airlines (AA 1951)
        • M
        • T
        • W
        • -
        • F
        • S
        • S
      • 17:00 SAN
        00:40 MDW
        5Hrs, 40m 1 Stop (PHX)
      • SANSan Diego International Airport 17:00 - MDW 00:40 5h 40m 1 Stop (PHX) Phoenix
      • SANSan Diego International Airport 17:00
        PHXPhoenix Sky Harbor Intl Airport 20:25
      • PHXPhoenix Sky Harbor Intl Airport 19:20
        MDWChicago Midway Airport 00:40
      • 5h 40m (1h 05m)
      • 1 Stop PHX · Phoenix 1h 05m
      • Southwest Airlines (WN 673)Boeing 737 700
        Southwest Airlines (WN 4574)Boeing 737 700
      • Southwest Airlines (WN 673)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 17:05 SAN
        01:15 MDW
        6Hrs, 10m 1 Stop (LAS)
      • SANSan Diego International Airport 17:05 - MDW 01:15 6h 10m 1 Stop (LAS) Las Vegas
      • SANSan Diego International Airport 17:05
        LASLas Vegas McCarran International Airport 19:50
      • LASLas Vegas McCarran International Airport 18:25
        MDWChicago Midway Airport 01:15
      • 6h 10m (1h 25m)
      • 1 Stop LAS · Las Vegas 1h 25m
      • Southwest Airlines (WN 1286)Boeing 737 700
        Southwest Airlines (WN 4188)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1286)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 17:10 SAN
        00:50 MDW
        5Hrs, 40m 1 Stop (DAL)
      • SANSan Diego International Airport 17:10 - MDW 00:50 5h 40m 1 Stop (DAL) Dallas
      • SANSan Diego International Airport 17:10
        DALDallas/Fort Worth Love Field Airport 22:45
      • DALDallas/Fort Worth Love Field Airport 22:00
        MDWChicago Midway Airport 00:50
      • 5h 40m (45m)
      • 1 Stop DAL · Dallas 45m
      • Southwest Airlines (WN 4782)Boeing 737 700
        Southwest Airlines (WN 5269)Boeing 737 700
      • Southwest Airlines (WN 4782)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 18:33 SAN
        03:22 ORD
        6Hrs, 49m 1 Stop (DEN)
      • SANSan Diego International Airport 18:33 - ORD 03:22 6h 49m 1 Stop (DEN) Denver
      • SANSan Diego International Airport 18:33
        DENDenver Intl Airport 23:55
      • DENDenver Intl Airport 22:00
        ORDChicago O'Hare International Airport 03:22
      • 6h 49m (1h 55m)
      • 1 Stop DEN · Denver 1h 55m
      • United Airlines (UA 1924)Boeing 737 800
        United Airlines (UA 1841)Boeing 737 Max 9 Passenger
      • United Airlines (UA 1924)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • 18:56 SAN
        04:00 ORD
        7Hrs, 04m 1 Stop (SFO)
      • SANSan Diego International Airport 18:56 - ORD 04:00 7h 04m 1 Stop (SFO) San Francisco
      • SANSan Diego International Airport 18:56
        SFOSan Francisco International Airport 21:40
      • SFOSan Francisco International Airport 20:35
        ORDChicago O'Hare International Airport 04:00
      • 7h 04m (1h 05m)
      • 1 Stop SFO · San Francisco 1h 05m
      • United Airlines (UA 2495)Boeing 737 800
        United Airlines (UA 1914)Boeing 737 800
      • United Airlines (UA 2495)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 18:56 SAN
        04:00 ORD
        7Hrs, 04m 1 Stop (SFO)
      • SANSan Diego International Airport 18:56 - ORD 04:00 7h 04m 1 Stop (SFO) San Francisco
      • SANSan Diego International Airport 18:56
        SFOSan Francisco International Airport 21:40
      • SFOSan Francisco International Airport 20:35
        ORDChicago O'Hare International Airport 04:00
      • 7h 04m (1h 05m)
      • 1 Stop SFO · San Francisco 1h 05m
      • United Airlines (UA 2495)Boeing 737 Max 8 Passenger
        United Airlines (UA 1914)Boeing 737 900
      • United Airlines (UA 2495)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 18:56 SAN
        05:00 ORD
        8Hrs, 04m 1 Stop (SFO)
      • SANSan Diego International Airport 18:56 - ORD 05:00 8h 04m 1 Stop (SFO) San Francisco
      • SANSan Diego International Airport 18:56
        SFOSan Francisco International Airport 22:44
      • SFOSan Francisco International Airport 20:35
        ORDChicago O'Hare International Airport 05:00
      • 8h 04m (2h 09m)
      • 1 Stop SFO · San Francisco 2h 09m
      • United Airlines (UA 2495)Boeing 737 800
        United Airlines (UA 1494)Boeing 757 300 Series
      • United Airlines (UA 2495)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 18:56 SAN
        05:04 ORD
        8Hrs, 08m 1 Stop (SFO)
      • SANSan Diego International Airport 18:56 - ORD 05:04 8h 08m 1 Stop (SFO) San Francisco
      • SANSan Diego International Airport 18:56
        SFOSan Francisco International Airport 22:44
      • SFOSan Francisco International Airport 20:35
        ORDChicago O'Hare International Airport 05:04
      • 8h 08m (2h 09m)
      • 1 Stop SFO · San Francisco 2h 09m
      • United Airlines (UA 2495)Boeing 737 Max 8 Passenger
        United Airlines (UA 1494)Airbus A321 Neo
      • United Airlines (UA 2495)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 18:56 SAN
        05:35 ORD
        8Hrs, 39m 1 Stop (SFO)
      • SANSan Diego International Airport 18:56 - ORD 05:35 8h 39m 1 Stop (SFO) San Francisco
      • SANSan Diego International Airport 18:56
        SFOSan Francisco International Airport 23:15
      • SFOSan Francisco International Airport 20:35
        ORDChicago O'Hare International Airport 05:35
      • 8h 39m (2h 40m)
      • 1 Stop SFO · San Francisco 2h 40m
      • United Airlines (UA 2495)Boeing 737 800
        United Airlines (UA 635)Boeing 737 900
      • United Airlines (UA 2495)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 18:57 SAN
        04:35 ORD
        7Hrs, 38m 1 Stop (LAS)
      • SANSan Diego International Airport 18:57 - ORD 04:35 7h 38m 1 Stop (LAS) Las Vegas
      • SANSan Diego International Airport 18:57
        LASLas Vegas McCarran International Airport 23:00
      • LASLas Vegas McCarran International Airport 20:16
        ORDChicago O'Hare International Airport 04:35
      • 7h 38m (2h 44m)
      • 1 Stop LAS · Las Vegas 2h 44m
      • Spirit Airlines (NK 2908)Airbus A320 Neo
        Spirit Airlines (NK 182)Airbus A320 Neo
      • Spirit Airlines (NK 2908)
        • M
        • T
        • W
        • -
        • F
        • S
        • S
      • 19:27 SAN
        05:15 ORD
        7Hrs, 48m 1 Stop (PHX)
      • SANSan Diego International Airport 19:27 - ORD 05:15 7h 48m 1 Stop (PHX) Phoenix
      • SANSan Diego International Airport 19:27
        PHXPhoenix Sky Harbor Intl Airport 00:45
      • PHXPhoenix Sky Harbor Intl Airport 21:50
        ORDChicago O'Hare International Airport 05:15
      • 7h 48m (2h 55m)
      • 1 Stop PHX · Phoenix 2h 55m
      • American Airlines (AA 480)Airbus A321 Neo
        American Airlines (AA 2723)Boeing 737 800
      • American Airlines (AA 480)
        • M
        • T
        • W
        • -
        • -
        • S
        • -
      • 19:27 SAN
        05:17 ORD
        7Hrs, 50m 1 Stop (PHX)
      • SANSan Diego International Airport 19:27 - ORD 05:17 7h 50m 1 Stop (PHX) Phoenix
      • SANSan Diego International Airport 19:27
        PHXPhoenix Sky Harbor Intl Airport 00:47
      • PHXPhoenix Sky Harbor Intl Airport 21:50
        ORDChicago O'Hare International Airport 05:17
      • 7h 50m (2h 57m)
      • 1 Stop PHX · Phoenix 2h 57m
      • American Airlines (AA 480)Airbus A321 Neo
        American Airlines (AA 1893)Boeing 737 800
      • American Airlines (AA 480)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 19:45 SAN
        05:00 ORD
        7Hrs, 15m 1 Stop (SFO)
      • SANSan Diego International Airport 19:45 - ORD 05:00 7h 15m 1 Stop (SFO) San Francisco
      • SANSan Diego International Airport 19:45
        SFOSan Francisco International Airport 22:44
      • SFOSan Francisco International Airport 21:24
        ORDChicago O'Hare International Airport 05:00
      • 7h 15m (1h 20m)
      • 1 Stop SFO · San Francisco 1h 20m
      • United Airlines (UA 564)Boeing 737 800
        United Airlines (UA 1494)Boeing 757 300 Series
      • United Airlines (UA 564)
        • M
        • T
        • W
        • -
        • F
        • -
        • S
      • 19:45 SAN
        05:04 ORD
        7Hrs, 19m 1 Stop (SFO)
      • SANSan Diego International Airport 19:45 - ORD 05:04 7h 19m 1 Stop (SFO) San Francisco
      • SANSan Diego International Airport 19:45
        SFOSan Francisco International Airport 22:44
      • SFOSan Francisco International Airport 21:24
        ORDChicago O'Hare International Airport 05:04
      • 7h 19m (1h 20m)
      • 1 Stop SFO · San Francisco 1h 20m
      • United Airlines (UA 564)Boeing 737 800
        United Airlines (UA 1494)Airbus A321 Neo
      • United Airlines (UA 564)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 19:45 SAN
        05:35 ORD
        7Hrs, 50m 1 Stop (SFO)
      • SANSan Diego International Airport 19:45 - ORD 05:35 7h 50m 1 Stop (SFO) San Francisco
      • SANSan Diego International Airport 19:45
        SFOSan Francisco International Airport 23:15
      • SFOSan Francisco International Airport 21:24
        ORDChicago O'Hare International Airport 05:35
      • 7h 50m (1h 51m)
      • 1 Stop SFO · San Francisco 1h 51m
      • United Airlines (UA 564)Boeing 737 800
        United Airlines (UA 635)Boeing 737 900
      • United Airlines (UA 564)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 19:45 SAN
        06:11 ORD
        8Hrs, 26m 1 Stop (SFO)
      • SANSan Diego International Airport 19:45 - ORD 06:11 8h 26m 1 Stop (SFO) San Francisco
      • SANSan Diego International Airport 19:45
        SFOSan Francisco International Airport 23:59
      • SFOSan Francisco International Airport 21:24
        ORDChicago O'Hare International Airport 06:11
      • 8h 26m (2h 35m)
      • 1 Stop SFO · San Francisco 2h 35m
      • United Airlines (UA 564)Boeing 737 800
        United Airlines (UA 476)Boeing 777
      • United Airlines (UA 564)
        • M
        • T
        • W
        • -
        • -
        • S
        • S
      • 19:55 SAN
        06:05 ORD
        8Hrs, 10m 1 Stop (SFO)
      • SANSan Diego International Airport 19:55 - ORD 06:05 8h 10m 1 Stop (SFO) San Francisco
      • SANSan Diego International Airport 19:55
        SFOSan Francisco International Airport 23:48
      • SFOSan Francisco International Airport 21:30
        ORDChicago O'Hare International Airport 06:05
      • 8h 10m (2h 18m)
      • 1 Stop SFO · San Francisco 2h 18m
      • Alaska Airlines (AS 717)Boeing 737 Max 9 Passenger
        American Airlines (AA 3100)Boeing 737 800
      • Alaska Airlines (AS 717)
        • M
        • T
        • W
        • -
        • F
        • -
        • S
      • 19:55 SAN
        06:05 ORD
        8Hrs, 10m 1 Stop (SFO)
      • SANSan Diego International Airport 19:55 - ORD 06:05 8h 10m 1 Stop (SFO) San Francisco
      • SANSan Diego International Airport 19:55
        SFOSan Francisco International Airport 23:48
      • SFOSan Francisco International Airport 21:30
        ORDChicago O'Hare International Airport 06:05
      • 8h 10m (2h 18m)
      • 1 Stop SFO · San Francisco 2h 18m
      • Alaska Airlines (AS 717)Boeing 737 Max 8 Passenger
        American Airlines (AA 3100)Boeing 737 800
      • Alaska Airlines (AS 717)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 19:59 SAN
        05:28 ORD
        7Hrs, 29m 1 Stop (PDX)
      • SANSan Diego International Airport 19:59 - ORD 05:28 7h 29m 1 Stop (PDX) Portland
      • SANSan Diego International Airport 19:59
        PDXPortland Airport 23:29
      • PDXPortland Airport 22:39
        ORDChicago O'Hare International Airport 05:28
      • 7h 29m (50m)
      • 1 Stop PDX · Portland 50m
      • Alaska Airlines (AS 403)Boeing 737 Max 9 Passenger
        Alaska Airlines (AS 340)Boeing 737
      • Alaska Airlines (AS 403)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 20:49 SAN
        05:01 ORD
        6Hrs, 12m 1 Stop (LAX)
      • SANSan Diego International Airport 20:49 - ORD 05:01 6h 12m 1 Stop (LAX) Los Angeles
      • SANSan Diego International Airport 20:49
        LAXLos Angeles International Airport 23:00
      • LAXLos Angeles International Airport 21:55
        ORDChicago O'Hare International Airport 05:01
      • 6h 12m (1h 05m)
      • 1 Stop LAX · Los Angeles 1h 05m
      • United Airlines (UA 5636)Embraer 175
        United Airlines (UA 2009)Boeing 777
      • United Airlines (UA 5636)
        • M
        • T
        • W
        • -
        • F
        • S
        • S
      • 20:49 SAN
        05:42 ORD
        6Hrs, 53m 1 Stop (LAX)
      • SANSan Diego International Airport 20:49 - ORD 05:42 6h 53m 1 Stop (LAX) Los Angeles
      • SANSan Diego International Airport 20:49
        LAXLos Angeles International Airport 23:35
      • LAXLos Angeles International Airport 21:55
        ORDChicago O'Hare International Airport 05:42
      • 6h 53m (1h 40m)
      • 1 Stop LAX · Los Angeles 1h 40m
      • United Airlines (UA 5636)Embraer 175
        United Airlines (UA 2101)Airbus A321 Neo
      • United Airlines (UA 5636)
        • -
        • T
        • W
        • -
        • -
        • S
        • S
      • 20:49 SAN
        05:42 ORD
        6Hrs, 53m 1 Stop (LAX)
      • SANSan Diego International Airport 20:49 - ORD 05:42 6h 53m 1 Stop (LAX) Los Angeles
      • SANSan Diego International Airport 20:49
        LAXLos Angeles International Airport 23:35
      • LAXLos Angeles International Airport 21:55
        ORDChicago O'Hare International Airport 05:42
      • 6h 53m (1h 40m)
      • 1 Stop LAX · Los Angeles 1h 40m
      • United Airlines (UA 5636)Embraer 175
        United Airlines (UA 2101)Boeing 737 900
      • United Airlines (UA 5636)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 21:00 SAN
        07:44 ORD
        8Hrs, 44m 1 Stop (EWR)
      • SANSan Diego International Airport 21:00 - ORD 07:44 8h 44m 1 Stop (EWR) New York City
      • SANSan Diego International Airport 21:00
        EWRNewark Liberty International Airport 06:00
      • EWRNewark Liberty International Airport 05:12
        ORDChicago O'Hare International Airport 07:44
      • 8h 44m (48m)
      • 1 Stop EWR · New York City 48m
      • United Airlines (UA 1827)Boeing 737 Max 8 Passenger
        United Airlines (UA 2164)Boeing 737 900
      • United Airlines (UA 1827)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 21:00 SAN
        07:44 ORD
        8Hrs, 44m 1 Stop (EWR)
      • SANSan Diego International Airport 21:00 - ORD 07:44 8h 44m 1 Stop (EWR) New York City
      • SANSan Diego International Airport 21:00
        EWRNewark Liberty International Airport 06:00
      • EWRNewark Liberty International Airport 05:12
        ORDChicago O'Hare International Airport 07:44
      • 8h 44m (48m)
      • 1 Stop EWR · New York City 48m
      • United Airlines (UA 1827)Boeing 737 Max 8 Passenger
        United Airlines (UA 2164)Boeing 757 200 Series
      • United Airlines (UA 1827)
        • M
        • -
        • W
        • T
        • F
        • S
        • S
      • 21:30 SAN
        05:17 ORD
        5Hrs, 47m 1 Stop (PHX)
      • SANSan Diego International Airport 21:30 - ORD 05:17 5h 47m 1 Stop (PHX) Phoenix
      • SANSan Diego International Airport 21:30
        PHXPhoenix Sky Harbor Intl Airport 00:47
      • PHXPhoenix Sky Harbor Intl Airport 23:51
        ORDChicago O'Hare International Airport 05:17
      • 5h 47m (56m)
      • 1 Stop PHX · Phoenix 56m
      • American Airlines (AA 3042)Airbus
        American Airlines (AA 1893)Boeing 737 800
      • American Airlines (AA 3042)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 21:30 SAN
        07:34 ORD
        8Hrs, 04m 1 Stop (IAD)
      • SANSan Diego International Airport 21:30 - ORD 07:34 8h 04m 1 Stop (IAD) Washington
      • SANSan Diego International Airport 21:30
        IADWashington Dulles International Airport 06:20
      • IADWashington Dulles International Airport 05:13
        ORDChicago O'Hare International Airport 07:34
      • 8h 04m (1h 07m)
      • 1 Stop IAD · Washington 1h 07m
      • United Airlines (UA 2129)Boeing 737 Max 9 Passenger
        United Airlines (UA 1316)Boeing 737 Max 9 Passenger
      • United Airlines (UA 2129)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 21:45 SAN
        07:34 ORD
        7Hrs, 49m 1 Stop (IAD)
      • SANSan Diego International Airport 21:45 - ORD 07:34 7h 49m 1 Stop (IAD) Washington
      • SANSan Diego International Airport 21:45
        IADWashington Dulles International Airport 06:20
      • IADWashington Dulles International Airport 05:28
        ORDChicago O'Hare International Airport 07:34
      • 7h 49m (52m)
      • 1 Stop IAD · Washington 52m
      • United Airlines (UA 2129)Boeing 737 Max 9 Passenger
        United Airlines (UA 1316)Boeing 737 Max 9 Passenger
      • United Airlines (UA 2129)
        • M
        • T
        • -
        • T
        • F
        • S
        • -
      • 21:55 SAN
        08:42 ORD
        8Hrs, 47m 1 Stop (CLT)
      • SANSan Diego International Airport 21:55 - ORD 08:42 8h 47m 1 Stop (CLT) Charlotte
      • SANSan Diego International Airport 21:55
        CLTCharlotte Airport 07:34
      • CLTCharlotte Airport 05:28
        ORDChicago O'Hare International Airport 08:42
      • 8h 47m (2h 06m)
      • 1 Stop CLT · Charlotte 2h 06m
      • American Airlines (AA 1706)Airbus
        American Airlines (AA 2843)Airbus
      • American Airlines (AA 1706)
        • M
        • T
        • W
        • -
        • F
        • S
        • S
      • 06:15 SAN
        16:34 ORD
        8Hrs, 19m 1 Stop (LAX)
      • SANSan Diego International Airport 06:15 - ORD 16:34 8h 19m 1 Stop (LAX) Los Angeles
      • SANSan Diego International Airport 06:15
        LAXLos Angeles International Airport 10:20
      • LAXLos Angeles International Airport 07:20
        ORDChicago O'Hare International Airport 16:34
      • 8h 19m (3h)
      • 1 Stop LAX · Los Angeles 3h
      • United Airlines (UA 4723)Embraer 175
        United Airlines (UA 1430)Boeing 737 Max 8 Passenger
      • United Airlines (UA 4723)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 06:15 SAN
        16:39 ORD
        8Hrs, 24m 1 Stop (LAX)
      • SANSan Diego International Airport 06:15 - ORD 16:39 8h 24m 1 Stop (LAX) Los Angeles
      • SANSan Diego International Airport 06:15
        LAXLos Angeles International Airport 10:25
      • LAXLos Angeles International Airport 07:20
        ORDChicago O'Hare International Airport 16:39
      • 8h 24m (3h 05m)
      • 1 Stop LAX · Los Angeles 3h 05m
      • United Airlines (UA 4723)Embraer 175
        United Airlines (UA 1430)Boeing 737 Max 9 Passenger
      • United Airlines (UA 4723)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 06:15 SAN
        16:53 ORD
        8Hrs, 38m 1 Stop (SEA)
      • SANSan Diego International Airport 06:15 - ORD 16:53 8h 38m 1 Stop (SEA) Seattle
      • SANSan Diego International Airport 06:15
        SEASeattle/Tacoma International Airport 10:35
      • SEASeattle/Tacoma International Airport 09:25
        ORDChicago O'Hare International Airport 16:53
      • 8h 38m (1h 10m)
      • 1 Stop SEA · Seattle 1h 10m
      • Alaska Airlines (AS 1245)Boeing 737 800
        Alaska Airlines (AS 352)Boeing 737
      • Alaska Airlines (AS 1245)
        • M
        • -
        • -
        • T
        • -
        • -
        • -
      • 06:15 SAN
        16:53 ORD
        8Hrs, 38m 1 Stop (SEA)
      • SANSan Diego International Airport 06:15 - ORD 16:53 8h 38m 1 Stop (SEA) Seattle
      • SANSan Diego International Airport 06:15
        SEASeattle/Tacoma International Airport 10:35
      • SEASeattle/Tacoma International Airport 09:24
        ORDChicago O'Hare International Airport 16:53
      • 8h 38m (1h 11m)
      • 1 Stop SEA · Seattle 1h 11m
      • Alaska Airlines (AS 1245)Boeing 737 800
        Alaska Airlines (AS 352)Boeing 737
      • Alaska Airlines (AS 1245)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 06:15 SAN
        16:53 ORD
        8Hrs, 38m 1 Stop (SEA)
      • SANSan Diego International Airport 06:15 - ORD 16:53 8h 38m 1 Stop (SEA) Seattle
      • SANSan Diego International Airport 06:15
        SEASeattle/Tacoma International Airport 10:35
      • SEASeattle/Tacoma International Airport 09:25
        ORDChicago O'Hare International Airport 16:53
      • 8h 38m (1h 10m)
      • 1 Stop SEA · Seattle 1h 10m
      • Alaska Airlines (AS 1245)Boeing 737 Max 9 Passenger
        Alaska Airlines (AS 352)Boeing 737
      • Alaska Airlines (AS 1245)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:15 SAN
        16:53 ORD
        8Hrs, 38m 1 Stop (SEA)
      • SANSan Diego International Airport 06:15 - ORD 16:53 8h 38m 1 Stop (SEA) Seattle
      • SANSan Diego International Airport 06:15
        SEASeattle/Tacoma International Airport 10:35
      • SEASeattle/Tacoma International Airport 09:25
        ORDChicago O'Hare International Airport 16:53
      • 8h 38m (1h 10m)
      • 1 Stop SEA · Seattle 1h 10m
      • Alaska Airlines (AS 1245)Boeing 737 800
        Alaska Airlines (AS 352)Boeing 737 900
      • Alaska Airlines (AS 1245)
        • -
        • -
        • W
        • -
        • -
        • S
        • -
      • 06:15 SAN
        16:53 ORD
        8Hrs, 38m 1 Stop (SEA)
      • SANSan Diego International Airport 06:15 - ORD 16:53 8h 38m 1 Stop (SEA) Seattle
      • SANSan Diego International Airport 06:15
        SEASeattle/Tacoma International Airport 10:35
      • SEASeattle/Tacoma International Airport 09:25
        ORDChicago O'Hare International Airport 16:53
      • 8h 38m (1h 10m)
      • 1 Stop SEA · Seattle 1h 10m
      • Alaska Airlines (AS 1245)Boeing 737 Max 9 Passenger
        Alaska Airlines (AS 352)Boeing 737 Max 9 Passenger
      • Alaska Airlines (AS 1245)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 06:15 SAN
        16:55 ORD
        8Hrs, 40m 1 Stop (SFO)
      • SANSan Diego International Airport 06:15 - ORD 16:55 8h 40m 1 Stop (SFO) San Francisco
      • SANSan Diego International Airport 06:15
        SFOSan Francisco International Airport 10:35
      • SFOSan Francisco International Airport 07:54
        ORDChicago O'Hare International Airport 16:55
      • 8h 40m (2h 41m)
      • 1 Stop SFO · San Francisco 2h 41m
      • United Airlines (UA 1986)Boeing 737 Max 8 Passenger
        United Airlines (UA 1612)Boeing 757 300 Series
      • United Airlines (UA 1986)
        • M
        • T
        • W
        • T
        • -
        • S
        • S
      • 06:15 SAN
        17:01 ORD
        8Hrs, 46m 1 Stop (LAX)
      • SANSan Diego International Airport 06:15 - ORD 17:01 8h 46m 1 Stop (LAX) Los Angeles
      • SANSan Diego International Airport 06:15
        LAXLos Angeles International Airport 10:47
      • LAXLos Angeles International Airport 07:20
        ORDChicago O'Hare International Airport 17:01
      • 8h 46m (3h 27m)
      • 1 Stop LAX · Los Angeles 3h 27m
      • United Airlines (UA 4723)Embraer 175
        United Airlines (UA 1430)Airbus A321 Neo
      • United Airlines (UA 4723)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 06:15 SAN
        16:44 ORD
        8Hrs, 29m 1 Stop (LAX)
      • SANSan Diego International Airport 06:15 - ORD 16:44 8h 29m 1 Stop (LAX) Los Angeles
      • SANSan Diego International Airport 06:15
        LAXLos Angeles International Airport 10:30
      • LAXLos Angeles International Airport 07:20
        ORDChicago O'Hare International Airport 16:44
      • 8h 29m (3h 10m)
      • 1 Stop LAX · Los Angeles 3h 10m
      • United Airlines (UA 4723)Embraer 175
        United Airlines (UA 1430)Boeing 737 800
      • United Airlines (UA 4723)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:15 SAN
        16:44 ORD
        8Hrs, 29m 1 Stop (LAX)
      • SANSan Diego International Airport 06:15 - ORD 16:44 8h 29m 1 Stop (LAX) Los Angeles
      • SANSan Diego International Airport 06:15
        LAXLos Angeles International Airport 10:30
      • LAXLos Angeles International Airport 07:20
        ORDChicago O'Hare International Airport 16:44
      • 8h 29m (3h 10m)
      • 1 Stop LAX · Los Angeles 3h 10m
      • United Airlines (UA 4723)Embraer 175
        United Airlines (UA 1430)Boeing 737 Max 8 Passenger
      • United Airlines (UA 4723)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:15 SAN
        16:44 ORD
        8Hrs, 29m 1 Stop (LAX)
      • SANSan Diego International Airport 06:15 - ORD 16:44 8h 29m 1 Stop (LAX) Los Angeles
      • SANSan Diego International Airport 06:15
        LAXLos Angeles International Airport 10:30
      • LAXLos Angeles International Airport 07:20
        ORDChicago O'Hare International Airport 16:44
      • 8h 29m (3h 10m)
      • 1 Stop LAX · Los Angeles 3h 10m
      • United Airlines (UA 4723)Embraer 175
        United Airlines (UA 1430)Boeing 737 Max 9 Passenger
      • United Airlines (UA 4723)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:15 SAN
        14:30 ORD
        6Hrs, 15m 1 Stop (LAX)
      • SANSan Diego International Airport 06:15 - ORD 14:30 6h 15m 1 Stop (LAX) Los Angeles
      • SANSan Diego International Airport 06:15
        LAXLos Angeles International Airport 08:15
      • LAXLos Angeles International Airport 07:20
        ORDChicago O'Hare International Airport 14:30
      • 6h 15m (55m)
      • 1 Stop LAX · Los Angeles 55m
      • United Airlines (UA 4723)Embraer 175
        United Airlines (UA 2039)Airbus A321 Neo
      • United Airlines (UA 4723)
        • M
        • T
        • W
        • -
        • F
        • S
        • S
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      What’s the fastest flight time from San Diego to Chicago?

      The fastest flight time for direct flights from San Diego to Chicago is 3 hours 50 minutes. Check latest flight schedules & prices on Wego.

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

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

      How far is Chicago from San Diego?

      The flight distance between San Diego and Chicago 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 06:15. The last flight of the day departs at 16:05. See the full list of flight times on Wego.

      How many airlines offer direct flights from San Diego to Chicago?

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

      Popular Airlines flying from San Diego to Chicago

      Frontier Airlines ‏()

      Popular Destinations from Chicago

      Popular Destinations from San Diego

      Popular Hotels in Chicago

      Hotels In Popular Destinations