Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Sun Country Airlines

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

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

Travel Period: October 2024 - September 2025

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

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

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

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

Flight Schedules

Last Updated: Mon, 2 Sep, 2024

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    • Airline Filter by Airline
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      • Availability
        • M
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      • 17:05 SAN
        23:00 MDW
        3Hrs, 55m Direct
      • SANSan Diego International Airport 17:05 - MDW 23:00 3h 55m Direct
      • SANSan Diego International Airport 17:05
      • MDWChicago Midway Airport 23:00
      • 3h 55m
      • Direct
      • Southwest Airlines (WN 3201)Boeing 737 700
      • Southwest Airlines (WN 3201)
        • -
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        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 17:40 SAN
        23:35 MDW
        3Hrs, 55m Direct
      • SANSan Diego International Airport 17:40 - MDW 23:35 3h 55m Direct
      • SANSan Diego International Airport 17:40
      • MDWChicago Midway Airport 23:35
      • 3h 55m
      • Direct
      • Southwest Airlines (WN 1498)Boeing 737 700
      • Southwest Airlines (WN 1498)
        • M
        • -
        • -
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        • F
        • -
        • -
      • Boeing 737 700
      • 18:20 SAN
        00:15 MDW
        3Hrs, 55m Direct
      • SANSan Diego International Airport 18:20 - MDW 00:15 3h 55m Direct
      • SANSan Diego International Airport 18:20
      • MDWChicago Midway Airport 00:15
      • 3h 55m
      • Direct
      • Southwest Airlines (WN 4938)Boeing 737 700
      • Southwest Airlines (WN 4938)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 22:29 SAN
        04:34 ORD
        4Hrs, 05m Direct
      • SANSan Diego International Airport 22:29 - ORD 04:34 4h 05m Direct
      • SANSan Diego International Airport 22:29
      • ORDChicago O'Hare International Airport 04:34
      • 4h 05m
      • Direct
      • United Airlines (UA 2352)Boeing 737 Max 9 Passenger
      • United Airlines (UA 2352)
        • -
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        • -
      • Boeing 737 Max 9 Passenger
      • 22:29 SAN
        04:34 ORD
        4Hrs, 05m Direct
      • SANSan Diego International Airport 22:29 - ORD 04:34 4h 05m Direct
      • SANSan Diego International Airport 22:29
      • ORDChicago O'Hare International Airport 04:34
      • 4h 05m
      • Direct
      • United Airlines (UA 2352)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2352)
        • M
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        • -
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        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 22:52 SAN
        05:00 ORD
        4Hrs, 08m Direct
      • SANSan Diego International Airport 22:52 - ORD 05:00 4h 08m Direct
      • SANSan Diego International Airport 22:52
      • ORDChicago O'Hare International Airport 05:00
      • 4h 08m
      • Direct
      • American Airlines (AA 2390)Airbus
      • American Airlines (AA 2390)
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        • 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 255)Boeing 737 800
      • Southwest Airlines (WN 255)
        • M
        • -
        • -
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        • F
        • -
        • -
      • Boeing 737 800
      • 06:20 SAN
        12:34 ORD
        4Hrs, 14m Direct
      • SANSan Diego International Airport 06:20 - ORD 12:34 4h 14m Direct
      • SANSan Diego International Airport 06:20
      • ORDChicago O'Hare International Airport 12:34
      • 4h 14m
      • Direct
      • American Airlines (AA 518)Airbus
      • American Airlines (AA 518)
        • M
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        • S
      • Airbus
      • 07:00 SAN
        13:15 ORD
        4Hrs, 15m Direct
      • SANSan Diego International Airport 07:00 - ORD 13:15 4h 15m Direct
      • SANSan Diego International Airport 07:00
      • ORDChicago O'Hare International Airport 13:15
      • 4h 15m
      • Direct
      • United Airlines (UA 1502)Airbus A321 Neo
      • United Airlines (UA 1502)
        • -
        • -
        • -
        • -
        • F
        • S
        • S
      • Airbus A321 Neo
      • 07:00 SAN
        13:12 ORD
        4Hrs, 12m Direct
      • SANSan Diego International Airport 07:00 - ORD 13:12 4h 12m Direct
      • SANSan Diego International Airport 07:00
      • ORDChicago O'Hare International Airport 13:12
      • 4h 12m
      • Direct
      • United Airlines (UA 1502)Boeing 737 800
      • United Airlines (UA 1502)
        • -
        • -
        • -
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        • -
        • -
        • -
      • Boeing 737 800
      • 07:00 SAN
        13:15 ORD
        4Hrs, 15m Direct
      • SANSan Diego International Airport 07:00 - ORD 13:15 4h 15m Direct
      • SANSan Diego International Airport 07:00
      • ORDChicago O'Hare International Airport 13:15
      • 4h 15m
      • Direct
      • United Airlines (UA 2042)Boeing 737 800
      • United Airlines (UA 2042)
        • M
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        • -
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 07:00 SAN
        13:15 ORD
        4Hrs, 15m Direct
      • SANSan Diego International Airport 07:00 - ORD 13:15 4h 15m Direct
      • SANSan Diego International Airport 07:00
      • ORDChicago O'Hare International Airport 13:15
      • 4h 15m
      • Direct
      • United Airlines (UA 2042)Boeing 737 900
      • United Airlines (UA 2042)
        • -
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        • -
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        • -
        • -
      • Boeing 737 900
      • 07:10 SAN
        16:10 MDW
        7Hrs, 00m Direct
      • SANSan Diego International Airport 07:10 - MDW 16:10 7h Direct
      • SANSan Diego International Airport 07:10
      • MDWChicago Midway Airport 16:10
      • 7h
      • Direct
      • Southwest Airlines (WN 1722)Boeing 737 700
      • Southwest Airlines (WN 1722)
        • -
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        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 08:05 SAN
        14:05 MDW
        4Hrs, 00m Direct
      • SANSan Diego International Airport 08:05 - MDW 14:05 4h Direct
      • SANSan Diego International Airport 08:05
      • MDWChicago Midway Airport 14:05
      • 4h
      • Direct
      • Southwest Airlines (WN 255)Boeing 737 800
      • Southwest Airlines (WN 255)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 800
      • 08:10 SAN
        14:10 MDW
        4Hrs, 00m Direct
      • SANSan Diego International Airport 08:10 - MDW 14:10 4h Direct
      • SANSan Diego International Airport 08:10
      • MDWChicago Midway Airport 14:10
      • 4h
      • Direct
      • Southwest Airlines (WN 255)Boeing 737 700
      • Southwest Airlines (WN 255)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 08:30 SAN
        14:45 ORD
        4Hrs, 15m Direct
      • SANSan Diego International Airport 08:30 - ORD 14:45 4h 15m Direct
      • SANSan Diego International Airport 08:30
      • ORDChicago O'Hare International Airport 14:45
      • 4h 15m
      • Direct
      • United Airlines (UA 1533)Boeing 737 800
      • United Airlines (UA 1533)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 08:30 SAN
        14:45 ORD
        4Hrs, 15m Direct
      • SANSan Diego International Airport 08:30 - ORD 14:45 4h 15m Direct
      • SANSan Diego International Airport 08:30
      • ORDChicago O'Hare International Airport 14:45
      • 4h 15m
      • Direct
      • United Airlines (UA 1533)Boeing 737 900
      • United Airlines (UA 1533)
        • -
        • -
        • -
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        • F
        • -
        • -
      • Boeing 737 900
      • 08:30 SAN
        14:45 ORD
        4Hrs, 15m Direct
      • SANSan Diego International Airport 08:30 - ORD 14:45 4h 15m Direct
      • SANSan Diego International Airport 08:30
      • ORDChicago O'Hare International Airport 14:45
      • 4h 15m
      • Direct
      • United Airlines (UA 1533)Boeing 737 Max 8 Passenger
      • United Airlines (UA 1533)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 08:45 SAN
        14:45 MDW
        4Hrs, 00m Direct
      • SANSan Diego International Airport 08:45 - MDW 14:45 4h Direct
      • SANSan Diego International Airport 08:45
      • MDWChicago Midway Airport 14:45
      • 4h
      • Direct
      • Southwest Airlines (WN 734)Boeing 737 800
      • Southwest Airlines (WN 734)
        • -
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        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 10:40 SAN
        18:00 MDW
        5Hrs, 20m Direct
      • SANSan Diego International Airport 10:40 - MDW 18:00 5h 20m Direct
      • SANSan Diego International Airport 10:40
      • MDWChicago Midway Airport 18:00
      • 5h 20m
      • Direct
      • Southwest Airlines (WN 597)Boeing 737 700
      • Southwest Airlines (WN 597)
        • M
        • -
        • -
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        • F
        • -
        • -
      • Boeing 737 700
      • 10:42 SAN
        16:57 ORD
        4Hrs, 15m Direct
      • SANSan Diego International Airport 10:42 - ORD 16:57 4h 15m Direct
      • SANSan Diego International Airport 10:42
      • ORDChicago O'Hare International Airport 16:57
      • 4h 15m
      • Direct
      • United Airlines (UA 714)Boeing 737 Max 8 Passenger
      • United Airlines (UA 714)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 10:42 SAN
        16:57 ORD
        4Hrs, 15m Direct
      • SANSan Diego International Airport 10:42 - ORD 16:57 4h 15m Direct
      • SANSan Diego International Airport 10:42
      • ORDChicago O'Hare International Airport 16:57
      • 4h 15m
      • Direct
      • United Airlines (UA 714)Airbus A321 Neo
      • United Airlines (UA 714)
        • -
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        • W
        • -
        • -
        • -
        • -
      • Airbus A321 Neo
      • 10:55 SAN
        17:10 ORD
        4Hrs, 15m Direct
      • SANSan Diego International Airport 10:55 - ORD 17:10 4h 15m Direct
      • SANSan Diego International Airport 10:55
      • ORDChicago O'Hare International Airport 17:10
      • 4h 15m
      • Direct
      • United Airlines (UA 714)Airbus A321 Neo
      • United Airlines (UA 714)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Airbus A321 Neo
      • 11:25 SAN
        17:25 MDW
        4Hrs, 00m Direct
      • SANSan Diego International Airport 11:25 - MDW 17:25 4h Direct
      • SANSan Diego International Airport 11:25
      • MDWChicago Midway Airport 17:25
      • 4h
      • Direct
      • Southwest Airlines (WN 1550)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1550)
        • M
        • -
        • -
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        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 11:32 SAN
        17:44 ORD
        4Hrs, 12m Direct
      • SANSan Diego International Airport 11:32 - ORD 17:44 4h 12m Direct
      • SANSan Diego International Airport 11:32
      • ORDChicago O'Hare International Airport 17:44
      • 4h 12m
      • Direct
      • American Airlines (AA 2343)Boeing 737 800
      • American Airlines (AA 2343)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 800
      • 11:40 SAN
        17:40 MDW
        4Hrs, 00m Direct
      • SANSan Diego International Airport 11:40 - MDW 17:40 4h Direct
      • SANSan Diego International Airport 11:40
      • MDWChicago Midway Airport 17:40
      • 4h
      • Direct
      • Southwest Airlines (WN 1550)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1550)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 11:43 SAN
        17:55 ORD
        4Hrs, 12m Direct
      • SANSan Diego International Airport 11:43 - ORD 17:55 4h 12m Direct
      • SANSan Diego International Airport 11:43
      • ORDChicago O'Hare International Airport 17:55
      • 4h 12m
      • Direct
      • American Airlines (AA 2343)Boeing 737 800
      • American Airlines (AA 2343)
        • -
        • T
        • W
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 12:05 SAN
        18:05 MDW
        4Hrs, 00m Direct
      • SANSan Diego International Airport 12:05 - MDW 18:05 4h Direct
      • SANSan Diego International Airport 12:05
      • MDWChicago Midway Airport 18:05
      • 4h
      • Direct
      • Southwest Airlines (WN 4410)Boeing 737 800
      • Southwest Airlines (WN 4410)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 800
      • 13:00 SAN
        19:00 MDW
        4Hrs, 00m Direct
      • SANSan Diego International Airport 13:00 - MDW 19:00 4h Direct
      • SANSan Diego International Airport 13:00
      • MDWChicago Midway Airport 19:00
      • 4h
      • Direct
      • Southwest Airlines (WN 948)Boeing 737 700
      • Southwest Airlines (WN 948)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 13:45 SAN
        23:20 MDW
        7Hrs, 35m Direct
      • SANSan Diego International Airport 13:45 - MDW 23:20 7h 35m Direct
      • SANSan Diego International Airport 13:45
      • MDWChicago Midway Airport 23:20
      • 7h 35m
      • Direct
      • Southwest Airlines (WN 1575)Boeing 737 700
      • Southwest Airlines (WN 1575)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 700
      • 14:00 SAN
        20:15 ORD
        4Hrs, 15m Direct
      • SANSan Diego International Airport 14:00 - ORD 20:15 4h 15m Direct
      • SANSan Diego International Airport 14:00
      • ORDChicago O'Hare International Airport 20:15
      • 4h 15m
      • Direct
      • United Airlines (UA 349)Boeing 737 Max 8 Passenger
      • United Airlines (UA 349)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 14:00 SAN
        20:15 ORD
        4Hrs, 15m Direct
      • SANSan Diego International Airport 14:00 - ORD 20:15 4h 15m Direct
      • SANSan Diego International Airport 14:00
      • ORDChicago O'Hare International Airport 20:15
      • 4h 15m
      • Direct
      • United Airlines (UA 1748)Boeing 737 Max 8 Passenger
      • United Airlines (UA 1748)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 14:00 SAN
        20:15 ORD
        4Hrs, 15m Direct
      • SANSan Diego International Airport 14:00 - ORD 20:15 4h 15m Direct
      • SANSan Diego International Airport 14:00
      • ORDChicago O'Hare International Airport 20:15
      • 4h 15m
      • Direct
      • United Airlines (UA 349)Boeing 737 Max 9 Passenger
      • United Airlines (UA 349)
        • -
        • -
        • -
        • -
        • F
        • S
        • S
      • Boeing 737 Max 9 Passenger
      • 14:00 SAN
        20:15 ORD
        4Hrs, 15m Direct
      • SANSan Diego International Airport 14:00 - ORD 20:15 4h 15m Direct
      • SANSan Diego International Airport 14:00
      • ORDChicago O'Hare International Airport 20:15
      • 4h 15m
      • Direct
      • United Airlines (UA 1748)Boeing 737 800
      • United Airlines (UA 1748)
        • M
        • T
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 14:20 SAN
        20:20 MDW
        4Hrs, 00m Direct
      • SANSan Diego International Airport 14:20 - MDW 20:20 4h Direct
      • SANSan Diego International Airport 14:20
      • MDWChicago Midway Airport 20:20
      • 4h
      • Direct
      • Southwest Airlines (WN 4348)Boeing 737 700
      • Southwest Airlines (WN 4348)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 700
      • 15:05 SAN
        21:00 MDW
        3Hrs, 55m Direct
      • SANSan Diego International Airport 15:05 - MDW 21:00 3h 55m Direct
      • SANSan Diego International Airport 15:05
      • MDWChicago Midway Airport 21:00
      • 3h 55m
      • Direct
      • Southwest Airlines (WN 3649)Boeing 737 700
      • Southwest Airlines (WN 3649)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 16:40 SAN
        22:44 ORD
        4Hrs, 04m Direct
      • SANSan Diego International Airport 16:40 - ORD 22:44 4h 04m Direct
      • SANSan Diego International Airport 16:40
      • ORDChicago O'Hare International Airport 22:44
      • 4h 04m
      • Direct
      • United Airlines (UA 2486)Boeing 757 200 Series
      • United Airlines (UA 2486)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 757 200 Series
      • 16:55 SAN
        22:59 ORD
        4Hrs, 04m Direct
      • SANSan Diego International Airport 16:55 - ORD 22:59 4h 04m Direct
      • SANSan Diego International Airport 16:55
      • ORDChicago O'Hare International Airport 22:59
      • 4h 04m
      • Direct
      • United Airlines (UA 2486)Boeing 757 200 Series
      • United Airlines (UA 2486)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Boeing 757 200 Series
      No Schedules Sorry, there are no schedules matching your filters. Try removing one. reset
      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 55 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 United 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 06:20. The last flight of the day departs at 17:05. 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

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

      Popular Destinations from Chicago

      Popular Destinations from San Diego

      Popular Hotels in Chicago

      Hotels In Popular Destinations