Fare Guide
Estimated lowest fares found within 7 days
The cheapest airline(s) flying from San Diego to Chicago is Sun Country Airlines.
Travel Period: October 2024 - September 2025
The cheapest month(s) to fly from San Diego to Chicago is December.
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Oct 2024
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Nov 2024
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Dec 2024
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Jan 2025
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Feb 2025
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Mar 2025
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Apr 2025
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May 2025
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Jun 2025
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Jul 2025
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Aug 2025
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Sep 2025
The cheapest day(s) of the week to fly from San Diego to Chicago is Sunday.
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Sun Sunday
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Mon Monday
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Tue Tuesday
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Wed Wednesday
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Thu Thursday
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Fri Friday
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Sat Saturday
Flight Schedules
Last Updated: Mon, 2 Sep, 2024
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Time
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17:05 SAN23:00 MDW3Hrs, 55m Direct
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SANSan Diego International Airport 17:05 - MDW 23:00 3h 55m Direct
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SANSan Diego International Airport 17:05
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MDWChicago Midway Airport 23:00
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Southwest Airlines (WN 3201)Boeing 737 700 -
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17:40 SAN23:35 MDW3Hrs, 55m Direct
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SANSan Diego International Airport 17:40 - MDW 23:35 3h 55m Direct
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SANSan Diego International Airport 17:40
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MDWChicago Midway Airport 23:35
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Southwest Airlines (WN 1498)Boeing 737 700 -
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18:20 SAN00:15 MDW3Hrs, 55m Direct
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SANSan Diego International Airport 18:20 - MDW 00:15 3h 55m Direct
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SANSan Diego International Airport 18:20
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MDWChicago Midway Airport 00:15
- 3h 55m
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Southwest Airlines (WN 4938)Boeing 737 700 -
Southwest Airlines (WN 4938) -
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22:29 SAN04:34 ORD4Hrs, 05m Direct
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SANSan Diego International Airport 22:29 - ORD 04:34 4h 05m Direct
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SANSan Diego International Airport 22:29
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ORDChicago O'Hare International Airport 04:34
- 4h 05m
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United Airlines (UA 2352)Boeing 737 Max 9 Passenger -
United Airlines (UA 2352) -
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22:29 SAN04:34 ORD4Hrs, 05m Direct
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SANSan Diego International Airport 22:29 - ORD 04:34 4h 05m Direct
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SANSan Diego International Airport 22:29
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ORDChicago O'Hare International Airport 04:34
- 4h 05m
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United Airlines (UA 2352)Boeing 737 Max 8 Passenger -
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22:52 SAN05:00 ORD4Hrs, 08m Direct
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SANSan Diego International Airport 22:52 - ORD 05:00 4h 08m Direct
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SANSan Diego International Airport 22:52
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ORDChicago O'Hare International Airport 05:00
- 4h 08m
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American Airlines (AA 2390)Airbus -
American Airlines (AA 2390) -
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06:20 SAN12:20 MDW4Hrs, 00m Direct
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SANSan Diego International Airport 06:20 - MDW 12:20 4h Direct
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SANSan Diego International Airport 06:20
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MDWChicago Midway Airport 12:20
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Southwest Airlines (WN 255)Boeing 737 800 -
Southwest Airlines (WN 255) -
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06:20 SAN12:34 ORD4Hrs, 14m Direct
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SANSan Diego International Airport 06:20 - ORD 12:34 4h 14m Direct
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SANSan Diego International Airport 06:20
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ORDChicago O'Hare International Airport 12:34
- 4h 14m
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American Airlines (AA 518)Airbus -
American Airlines (AA 518) -
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07:00 SAN13:15 ORD4Hrs, 15m Direct
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SANSan Diego International Airport 07:00 - ORD 13:15 4h 15m Direct
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SANSan Diego International Airport 07:00
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ORDChicago O'Hare International Airport 13:15
- 4h 15m
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United Airlines (UA 1502)Airbus A321 Neo -
United Airlines (UA 1502) -
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07:00 SAN13:12 ORD4Hrs, 12m Direct
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SANSan Diego International Airport 07:00 - ORD 13:12 4h 12m Direct
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SANSan Diego International Airport 07:00
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ORDChicago O'Hare International Airport 13:12
- 4h 12m
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07:00 SAN13:15 ORD4Hrs, 15m Direct
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SANSan Diego International Airport 07:00 - ORD 13:15 4h 15m Direct
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SANSan Diego International Airport 07:00
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ORDChicago O'Hare International Airport 13:15
- 4h 15m
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United Airlines (UA 2042)Boeing 737 800 -
United Airlines (UA 2042) -
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07:00 SAN13:15 ORD4Hrs, 15m Direct
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SANSan Diego International Airport 07:00 - ORD 13:15 4h 15m Direct
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SANSan Diego International Airport 07:00
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ORDChicago O'Hare International Airport 13:15
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United Airlines (UA 2042)Boeing 737 900 -
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07:10 SAN16:10 MDW7Hrs, 00m Direct
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SANSan Diego International Airport 07:10 - MDW 16:10 7h Direct
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SANSan Diego International Airport 07:10
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MDWChicago Midway Airport 16:10
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Southwest Airlines (WN 1722)Boeing 737 700 -
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08:05 SAN14:05 MDW4Hrs, 00m Direct
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SANSan Diego International Airport 08:05 - MDW 14:05 4h Direct
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SANSan Diego International Airport 08:05
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MDWChicago Midway Airport 14:05
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Southwest Airlines (WN 255)Boeing 737 800 -
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08:10 SAN14:10 MDW4Hrs, 00m Direct
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SANSan Diego International Airport 08:10 - MDW 14:10 4h Direct
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SANSan Diego International Airport 08:10
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MDWChicago Midway Airport 14:10
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Southwest Airlines (WN 255)Boeing 737 700 -
Southwest Airlines (WN 255) -
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08:30 SAN14:45 ORD4Hrs, 15m Direct
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SANSan Diego International Airport 08:30 - ORD 14:45 4h 15m Direct
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SANSan Diego International Airport 08:30
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ORDChicago O'Hare International Airport 14:45
- 4h 15m
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United Airlines (UA 1533)Boeing 737 800 -
United Airlines (UA 1533) -
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08:30 SAN14:45 ORD4Hrs, 15m Direct
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SANSan Diego International Airport 08:30 - ORD 14:45 4h 15m Direct
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SANSan Diego International Airport 08:30
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ORDChicago O'Hare International Airport 14:45
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United Airlines (UA 1533)Boeing 737 900 -
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08:30 SAN14:45 ORD4Hrs, 15m Direct
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SANSan Diego International Airport 08:30 - ORD 14:45 4h 15m Direct
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SANSan Diego International Airport 08:30
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ORDChicago O'Hare International Airport 14:45
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United Airlines (UA 1533)Boeing 737 Max 8 Passenger -
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08:45 SAN14:45 MDW4Hrs, 00m Direct
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SANSan Diego International Airport 08:45 - MDW 14:45 4h Direct
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SANSan Diego International Airport 08:45
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MDWChicago Midway Airport 14:45
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Southwest Airlines (WN 734)Boeing 737 800 -
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10:40 SAN18:00 MDW5Hrs, 20m Direct
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SANSan Diego International Airport 10:40 - MDW 18:00 5h 20m Direct
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SANSan Diego International Airport 10:40
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MDWChicago Midway Airport 18:00
- 5h 20m
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Southwest Airlines (WN 597)Boeing 737 700 -
Southwest Airlines (WN 597) -
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10:42 SAN16:57 ORD4Hrs, 15m Direct
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SANSan Diego International Airport 10:42 - ORD 16:57 4h 15m Direct
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SANSan Diego International Airport 10:42
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ORDChicago O'Hare International Airport 16:57
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United Airlines (UA 714)Boeing 737 Max 8 Passenger -
United Airlines (UA 714) -
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10:42 SAN16:57 ORD4Hrs, 15m Direct
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SANSan Diego International Airport 10:42 - ORD 16:57 4h 15m Direct
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SANSan Diego International Airport 10:42
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ORDChicago O'Hare International Airport 16:57
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United Airlines (UA 714)Airbus A321 Neo -
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10:55 SAN17:10 ORD4Hrs, 15m Direct
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SANSan Diego International Airport 10:55 - ORD 17:10 4h 15m Direct
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SANSan Diego International Airport 10:55
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ORDChicago O'Hare International Airport 17:10
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United Airlines (UA 714)Airbus A321 Neo -
United Airlines (UA 714) -
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11:25 SAN17:25 MDW4Hrs, 00m Direct
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SANSan Diego International Airport 11:25 - MDW 17:25 4h Direct
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SANSan Diego International Airport 11:25
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MDWChicago Midway Airport 17:25
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Southwest Airlines (WN 1550)Boeing 737 Max 8 Passenger -
Southwest Airlines (WN 1550) -
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11:32 SAN17:44 ORD4Hrs, 12m Direct
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SANSan Diego International Airport 11:32 - ORD 17:44 4h 12m Direct
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SANSan Diego International Airport 11:32
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ORDChicago O'Hare International Airport 17:44
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American Airlines (AA 2343)Boeing 737 800 -
American Airlines (AA 2343) -
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11:40 SAN17:40 MDW4Hrs, 00m Direct
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SANSan Diego International Airport 11:40 - MDW 17:40 4h Direct
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SANSan Diego International Airport 11:40
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MDWChicago Midway Airport 17:40
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Southwest Airlines (WN 1550)Boeing 737 Max 8 Passenger -
Southwest Airlines (WN 1550) -
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11:43 SAN17:55 ORD4Hrs, 12m Direct
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SANSan Diego International Airport 11:43 - ORD 17:55 4h 12m Direct
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SANSan Diego International Airport 11:43
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ORDChicago O'Hare International Airport 17:55
- 4h 12m
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American Airlines (AA 2343)Boeing 737 800 -
American Airlines (AA 2343) -
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12:05 SAN18:05 MDW4Hrs, 00m Direct
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SANSan Diego International Airport 12:05 - MDW 18:05 4h Direct
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SANSan Diego International Airport 12:05
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MDWChicago Midway Airport 18:05
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Southwest Airlines (WN 4410)Boeing 737 800 -
Southwest Airlines (WN 4410) -
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13:00 SAN19:00 MDW4Hrs, 00m Direct
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SANSan Diego International Airport 13:00 - MDW 19:00 4h Direct
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SANSan Diego International Airport 13:00
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MDWChicago Midway Airport 19:00
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Southwest Airlines (WN 948)Boeing 737 700 -
Southwest Airlines (WN 948) -
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13:45 SAN23:20 MDW7Hrs, 35m Direct
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SANSan Diego International Airport 13:45 - MDW 23:20 7h 35m Direct
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SANSan Diego International Airport 13:45
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MDWChicago Midway Airport 23:20
- 7h 35m
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Southwest Airlines (WN 1575)Boeing 737 700 -
Southwest Airlines (WN 1575) -
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14:00 SAN20:15 ORD4Hrs, 15m Direct
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SANSan Diego International Airport 14:00 - ORD 20:15 4h 15m Direct
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SANSan Diego International Airport 14:00
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ORDChicago O'Hare International Airport 20:15
- 4h 15m
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United Airlines (UA 349)Boeing 737 Max 8 Passenger -
United Airlines (UA 349) -
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14:00 SAN20:15 ORD4Hrs, 15m Direct
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SANSan Diego International Airport 14:00 - ORD 20:15 4h 15m Direct
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SANSan Diego International Airport 14:00
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ORDChicago O'Hare International Airport 20:15
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United Airlines (UA 1748)Boeing 737 Max 8 Passenger -
United Airlines (UA 1748) -
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14:00 SAN20:15 ORD4Hrs, 15m Direct
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SANSan Diego International Airport 14:00 - ORD 20:15 4h 15m Direct
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SANSan Diego International Airport 14:00
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ORDChicago O'Hare International Airport 20:15
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United Airlines (UA 349)Boeing 737 Max 9 Passenger -
United Airlines (UA 349) -
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14:00 SAN20:15 ORD4Hrs, 15m Direct
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SANSan Diego International Airport 14:00 - ORD 20:15 4h 15m Direct
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SANSan Diego International Airport 14:00
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ORDChicago O'Hare International Airport 20:15
- 4h 15m
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United Airlines (UA 1748)Boeing 737 800 -
United Airlines (UA 1748) -
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14:20 SAN20:20 MDW4Hrs, 00m Direct
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SANSan Diego International Airport 14:20 - MDW 20:20 4h Direct
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SANSan Diego International Airport 14:20
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MDWChicago Midway Airport 20:20
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Southwest Airlines (WN 4348)Boeing 737 700 -
Southwest Airlines (WN 4348) -
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15:05 SAN21:00 MDW3Hrs, 55m Direct
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SANSan Diego International Airport 15:05 - MDW 21:00 3h 55m Direct
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SANSan Diego International Airport 15:05
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MDWChicago Midway Airport 21:00
- 3h 55m
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Southwest Airlines (WN 3649)Boeing 737 700 -
Southwest Airlines (WN 3649) -
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16:40 SAN22:44 ORD4Hrs, 04m Direct
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SANSan Diego International Airport 16:40 - ORD 22:44 4h 04m Direct
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SANSan Diego International Airport 16:40
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ORDChicago O'Hare International Airport 22:44
- 4h 04m
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United Airlines (UA 2486)Boeing 757 200 Series -
United Airlines (UA 2486) -
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- Boeing 757 200 Series
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16:55 SAN22:59 ORD4Hrs, 04m Direct
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SANSan Diego International Airport 16:55 - ORD 22:59 4h 04m Direct
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SANSan Diego International Airport 16:55
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ORDChicago O'Hare International Airport 22:59
- 4h 04m
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United Airlines (UA 2486)Boeing 757 200 Series -
United Airlines (UA 2486) -
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- Boeing 757 200 Series
The fastest flight time for direct flights from San Diego to Chicago is 3 hours 55 minutes. Check latest flight schedules & prices on Wego.
The most popular airline flying from San Diego to Chicago is United Airlines. Find the latest flight deals on Wego.
The flight distance between San Diego and Chicago is 2787km. Check all available flights on Wego.
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.
There are 3 airlines that offer direct flights from San Diego to Chicago. Find out the list of airlines on Wego.
All Airports in San Diego
All Airports in Chicago
Popular Airlines flying from San Diego to Chicago
Popular Destinations from Chicago
Popular Destinations from San Diego
Popular Hotels in Chicago
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- Swissôtel Chicago
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