Fare Guide

Estimated lowest fares found within 7 days

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

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

  • Spirit Airlines Spirit Airlines
  • Frontier Airlines Frontier Airlines
  • Alaska Airlines Alaska Airlines
  • Southwest Airlines Southwest Airlines
  • American Airlines American Airlines
  • JetBlue Airways JetBlue Airways
  • Hawaiian Airlines Hawaiian Airlines
  • United Airlines United Airlines
  • Sun Country Airlines Sun Country Airlines
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
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        • S
      • 19:20 MDW
        23:10 SAN
        5Hrs, 50m Direct
      • MDWChicago Midway Airport 19:20 - SAN 23:10 5h 50m Direct
      • MDWChicago Midway Airport 19:20
      • SANSan Diego International Airport 23:10
      • 5h 50m
      • Direct
      • Southwest Airlines (WN 3669)Boeing 737 700
      • Southwest Airlines (WN 3669)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 700
      • 19:25 MDW
        21:55 SAN
        4Hrs, 30m Direct
      • MDWChicago Midway Airport 19:25 - SAN 21:55 4h 30m Direct
      • MDWChicago Midway Airport 19:25
      • SANSan Diego International Airport 21:55
      • 4h 30m
      • Direct
      • Southwest Airlines (WN 3595)Boeing 737 700
      • Southwest Airlines (WN 3595)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 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)
        • -
        • T
        • W
        • T
        • F
        • -
        • S
      • Boeing 737 800
      • 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 1828)Boeing 737 800
      • United Airlines (UA 1828)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 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
      • 20:05 MDW
        22:35 SAN
        4Hrs, 30m Direct
      • MDWChicago Midway Airport 20:05 - SAN 22:35 4h 30m Direct
      • MDWChicago Midway Airport 20:05
      • SANSan Diego International Airport 22:35
      • 4h 30m
      • Direct
      • Southwest Airlines (WN 2690)Boeing 737 700
      • Southwest Airlines (WN 2690)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 20:10 MDW
        22:40 SAN
        4Hrs, 30m Direct
      • MDWChicago Midway Airport 20:10 - SAN 22:40 4h 30m Direct
      • MDWChicago Midway Airport 20:10
      • SANSan Diego International Airport 22:40
      • 4h 30m
      • Direct
      • Southwest Airlines (WN 3595)Boeing 737 700
      • Southwest Airlines (WN 3595)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 20:55 MDW
        23:25 SAN
        4Hrs, 30m Direct
      • MDWChicago Midway Airport 20:55 - SAN 23:25 4h 30m Direct
      • MDWChicago Midway Airport 20:55
      • SANSan Diego International Airport 23:25
      • 4h 30m
      • Direct
      • Southwest Airlines (WN 3595)Boeing 737 700
      • Southwest Airlines (WN 3595)
        • M
        • -
        • -
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        • 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)
        • -
        • -
        • -
        • -
        • F
        • S
        • S
      • Airbus
      • 21:07 ORD
        23:34 SAN
        4Hrs, 27m Direct
      • ORDChicago O'Hare International Airport 21:07 - SAN 23:34 4h 27m Direct
      • ORDChicago O'Hare International Airport 21:07
      • SANSan Diego International Airport 23:34
      • 4h 27m
      • Direct
      • American Airlines (AA 1861)Airbus
      • American Airlines (AA 1861)
        • M
        • T
        • W
        • T
        • -
        • -
        • -
      • Airbus
      • 06:48 ORD
        09:09 SAN
        4Hrs, 21m Direct
      • ORDChicago O'Hare International Airport 06:48 - SAN 09:09 4h 21m Direct
      • ORDChicago O'Hare International Airport 06:48
      • SANSan Diego International Airport 09:09
      • 4h 21m
      • Direct
      • American Airlines (AA 2131)Airbus
      • American Airlines (AA 2131)
        • -
        • -
        • -
        • -
        • -
        • 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)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • Boeing 737 800
      • 07:55 MDW
        10:25 SAN
        4Hrs, 30m Direct
      • MDWChicago Midway Airport 07:55 - SAN 10:25 4h 30m Direct
      • MDWChicago Midway Airport 07:55
      • SANSan Diego International Airport 10:25
      • 4h 30m
      • Direct
      • Southwest Airlines (WN 581)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 581)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 08:15 MDW
        10:40 SAN
        4Hrs, 25m Direct
      • MDWChicago Midway Airport 08:15 - SAN 10:40 4h 25m Direct
      • MDWChicago Midway Airport 08:15
      • SANSan Diego International Airport 10:40
      • 4h 25m
      • Direct
      • Southwest Airlines (WN 816)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 816)
        • M
        • -
        • -
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        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 08:30 MDW
        11:00 SAN
        4Hrs, 30m Direct
      • MDWChicago Midway Airport 08:30 - SAN 11:00 4h 30m Direct
      • MDWChicago Midway Airport 08:30
      • SANSan Diego International Airport 11:00
      • 4h 30m
      • Direct
      • Southwest Airlines (WN 1404)Boeing 737 700
      • Southwest Airlines (WN 1404)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 08:40 MDW
        11:10 SAN
        4Hrs, 30m Direct
      • MDWChicago Midway Airport 08:40 - SAN 11:10 4h 30m Direct
      • MDWChicago Midway Airport 08:40
      • SANSan Diego International Airport 11:10
      • 4h 30m
      • Direct
      • Southwest Airlines (WN 3595)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3595)
        • -
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        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 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)Boeing 737 900
      • United Airlines (UA 660)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 900
      • 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)
        • -
        • T
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        • T
        • F
        • S
        • S
      • Airbus A321 Neo
      • 10:08 ORD
        12:39 SAN
        4Hrs, 31m Direct
      • ORDChicago O'Hare International Airport 10:08 - SAN 12:39 4h 31m Direct
      • ORDChicago O'Hare International Airport 10:08
      • SANSan Diego International Airport 12:39
      • 4h 31m
      • Direct
      • American Airlines (AA 2131)Boeing 737 800
      • American Airlines (AA 2131)
        • M
        • T
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        • T
        • -
        • -
        • -
      • Boeing 737 800
      • 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)
        • -
        • -
        • -
        • -
        • F
        • -
        • 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 737 900
      • United Airlines (UA 2294)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Boeing 737 900
      • 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
        • -
        • S
        • S
      • Boeing 737 800
      • 12:05 MDW
        16:45 SAN
        6Hrs, 40m Direct
      • MDWChicago Midway Airport 12:05 - SAN 16:45 6h 40m Direct
      • MDWChicago Midway Airport 12:05
      • SANSan Diego International Airport 16:45
      • 6h 40m
      • Direct
      • Southwest Airlines (WN 3339)Boeing 737 700
      • Southwest Airlines (WN 3339)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 12:20 MDW
        14:50 SAN
        4Hrs, 30m Direct
      • MDWChicago Midway Airport 12:20 - SAN 14:50 4h 30m Direct
      • MDWChicago Midway Airport 12:20
      • SANSan Diego International Airport 14:50
      • 4h 30m
      • Direct
      • Southwest Airlines (WN 2272)Boeing 737 700
      • Southwest Airlines (WN 2272)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 700
      • 13:25 MDW
        17:30 SAN
        6Hrs, 05m Direct
      • MDWChicago Midway Airport 13:25 - SAN 17:30 6h 05m Direct
      • MDWChicago Midway Airport 13:25
      • SANSan Diego International Airport 17:30
      • 6h 05m
      • Direct
      • Southwest Airlines (WN 2723)Boeing 737 700
      • Southwest Airlines (WN 2723)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 13:40 MDW
        16:10 SAN
        4Hrs, 30m Direct
      • MDWChicago Midway Airport 13:40 - SAN 16:10 4h 30m Direct
      • MDWChicago Midway Airport 13:40
      • SANSan Diego International Airport 16:10
      • 4h 30m
      • Direct
      • Southwest Airlines (WN 4022)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4022)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 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
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        • T
        • F
        • S
        • S
      • Boeing 737 Max 8 Passenger
      • 13:45 MDW
        18:45 SAN
        7Hrs, 00m Direct
      • MDWChicago Midway Airport 13:45 - SAN 18:45 7h Direct
      • MDWChicago Midway Airport 13:45
      • SANSan Diego International Airport 18:45
      • 7h
      • Direct
      • Southwest Airlines (WN 498)Boeing 737 700
      • Southwest Airlines (WN 498)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 700
      • 13:45 MDW
        16:15 SAN
        4Hrs, 30m Direct
      • MDWChicago Midway Airport 13:45 - SAN 16:15 4h 30m Direct
      • MDWChicago Midway Airport 13:45
      • SANSan Diego International Airport 16:15
      • 4h 30m
      • Direct
      • Southwest Airlines (WN 816)Boeing 737 700
      • Southwest Airlines (WN 816)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 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 737 900
      • United Airlines (UA 1373)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 900
      • 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)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Boeing 757 300 Series
      • 14:40 MDW
        18:15 SAN
        5Hrs, 35m Direct
      • MDWChicago Midway Airport 14:40 - SAN 18:15 5h 35m Direct
      • MDWChicago Midway Airport 14:40
      • SANSan Diego International Airport 18:15
      • 5h 35m
      • Direct
      • Southwest Airlines (WN 2455)Boeing 737 700
      • Southwest Airlines (WN 2455)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 700
      • 15:55 MDW
        18:25 SAN
        4Hrs, 30m Direct
      • MDWChicago Midway Airport 15:55 - SAN 18:25 4h 30m Direct
      • MDWChicago Midway Airport 15:55
      • SANSan Diego International Airport 18:25
      • 4h 30m
      • Direct
      • Southwest Airlines (WN 2891)Boeing 737 800
      • Southwest Airlines (WN 2891)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 800
      • 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
      • 16:40 MDW
        23:15 SAN
        8Hrs, 35m Direct
      • MDWChicago Midway Airport 16:40 - SAN 23:15 8h 35m Direct
      • MDWChicago Midway Airport 16:40
      • SANSan Diego International Airport 23:15
      • 8h 35m
      • Direct
      • Southwest Airlines (WN 3669)Boeing 737 700
      • Southwest Airlines (WN 3669)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 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)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • Airbus
      • 16:55 ORD
        19:17 SAN
        4Hrs, 22m Direct
      • ORDChicago O'Hare International Airport 16:55 - SAN 19:17 4h 22m Direct
      • ORDChicago O'Hare International Airport 16:55
      • SANSan Diego International Airport 19:17
      • 4h 22m
      • Direct
      • American Airlines (AA 1543)Airbus
      • American Airlines (AA 1543)
        • M
        • T
        • W
        • T
        • -
        • -
        • -
      • Airbus
      • 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)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Airbus
      No Schedules Sorry, there are no schedules matching your filters. Try removing one. reset
      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 19 minutes. Check latest flight schedules & prices 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 06:48. The last flight of the day departs at 19:20. 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.

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