Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from San Diego to Chicago is Frontier Airlines.
Cheapest Month
May
Travel Period: May 2024 - April 2025
The cheapest month(s) to fly from San Diego to Chicago is May.
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May 2024
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Jun 2024
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Jul 2024
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Aug 2024
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Sep 2024
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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
Cheapest Day of the Week
Monday
The cheapest day(s) of the week to fly from San Diego to Chicago is Monday.
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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
Cheapest Time
8am
The cheapest time of the day to fly from San Diego to Chicago is in the morning.
Early Morning 12:01am - 06:00am
Morning 6:01am - 12:00pm
Afternoon 12:01pm - 6:00pm
Evening 6:01pm to 12:00am
12am
6am
12pm
6pm
Flight Schedules
Last Updated: Tue, 2 Apr, 2024
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Earliest
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Total Duration
- Shortest
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All
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Availability
- M
- T
- W
- T
- F
- S
- S
-
17:45 - 23:35SAN - MDW
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17:45 (SAN)San Diego International Airport
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23:35 (MDW)Chicago Midway Airport
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(WN 1379)Boeing 737 700 - 3h 50m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
18:15 - 00:10+ 1SAN - MDW
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18:15 (SAN)San Diego International Airport
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00:10 (MDW)Chicago Midway Airport + 1
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(WN 1379)Boeing 737 700 - 3h 55m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
-
18:30 - 00:20+ 1SAN - MDW
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18:30 (SAN)San Diego International Airport
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00:20 (MDW)Chicago Midway Airport + 1
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(WN 3223)Boeing 737 700 - 3h 50m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
-
22:30 - 04:39+ 1SAN - ORD
-
22:30 (SAN)San Diego International Airport
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04:39 (ORD)Chicago O'Hare International Airport + 1
-
United Airlines (UA 1506)Boeing 737 800 - 4h 09m
- Direct
-
- M
- T
- W
- T
- F
- -
- S
- Boeing 737 800
-
22:45 - 05:00+ 1SAN - ORD
-
22:45 (SAN)San Diego International Airport
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05:00 (ORD)Chicago O'Hare International Airport + 1
-
American Airlines (AA 2065)Airbus - 4h 15m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus
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06:23 - 12:40SAN - ORD
-
06:23 (SAN)San Diego International Airport
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12:40 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 518)Airbus - 4h 17m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus
-
06:30 - 12:30SAN - MDW
-
06:30 (SAN)San Diego International Airport
-
12:30 (MDW)Chicago Midway Airport
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(WN 2194)Boeing 737 700 - 4h
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
07:00 - 12:55SAN - ORD
-
07:00 (SAN)San Diego International Airport
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12:55 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1502)Boeing 737 800 - 3h 55m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
07:40 - 13:35SAN - MDW
-
07:40 (SAN)San Diego International Airport
-
13:35 (MDW)Chicago Midway Airport
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(WN 1379)Boeing 737 700 - 3h 55m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
-
07:45 - 13:40SAN - MDW
-
07:45 (SAN)San Diego International Airport
-
13:40 (MDW)Chicago Midway Airport
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(WN 2194)Boeing 737 700 - 3h 55m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
-
08:05 - 15:35SAN - ORD
-
08:05 (SAN)San Diego International Airport
-
15:35 (ORD)Chicago O'Hare International Airport
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(WN 4161)Boeing 737 700 - 5h 30m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
-
09:20 - 15:10SAN - MDW
-
09:20 (SAN)San Diego International Airport
-
15:10 (MDW)Chicago Midway Airport
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(WN 2194)Boeing 737 700 - 3h 50m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
09:56 - 20:10SAN - ORD
-
09:56 (SAN)San Diego International Airport
-
20:10 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 2627)Boeing 737 800 - 8h 14m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
11:06 - 17:10SAN - ORD
-
11:06 (SAN)San Diego International Airport
-
17:10 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 2325)Boeing 737 800 - 4h 04m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
11:31 - 17:45SAN - ORD
-
11:31 (SAN)San Diego International Airport
-
17:45 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 2343)Boeing 737 800 - 4h 14m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
12:35 - 18:30SAN - MDW
-
12:35 (SAN)San Diego International Airport
-
18:30 (MDW)Chicago Midway Airport
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(WN 106)Boeing 737 800 - 3h 55m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
-
12:40 - 18:35SAN - MDW
-
12:40 (SAN)San Diego International Airport
-
18:35 (MDW)Chicago Midway Airport
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(WN 106)Boeing 737 Max 8 Passenger - 3h 55m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
-
13:50 - 19:45SAN - MDW
-
13:50 (SAN)San Diego International Airport
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19:45 (MDW)Chicago Midway Airport
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(WN 171)Boeing 737 800 - 3h 55m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
-
14:09 - 20:03SAN - ORD
-
14:09 (SAN)San Diego International Airport
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20:03 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1774)Boeing 737 800 - 3h 54m
- Direct
-
- M
- T
- W
- T
- F
- -
- S
- Boeing 737 800
-
14:40 - 23:00SAN - MDW
-
14:40 (SAN)San Diego International Airport
-
23:00 (MDW)Chicago Midway Airport
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(WN 4143)Boeing 737 700 - 6h 20m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
-
15:45 - 22:40SAN - MDW
-
15:45 (SAN)San Diego International Airport
-
22:40 (MDW)Chicago Midway Airport
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(WN 282)Boeing 737 700 - 4h 55m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
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16:30 - 22:20SAN - MDW
-
16:30 (SAN)San Diego International Airport
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22:20 (MDW)Chicago Midway Airport
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(WN 106)Boeing 737 700 - 3h 50m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
16:45 - 22:49SAN - ORD
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16:45 (SAN)San Diego International Airport
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22:49 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 2486)Boeing 737 800 - 4h 04m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
Connecting Flights
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17:35 - 18:55+ 1SAN - PHX19:50 - 01:05+ 1PHX - MDW
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17:35 (SAN)San Diego International Airport19:50 (PHX)Phoenix Sky Harbor Intl Airport
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18:55 (PHX)Phoenix Sky Harbor Intl Airport + 101:05 (MDW)Chicago Midway Airport
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(WN 5122)Boeing 737 700 (WN 3204)Boeing 737 800 - 5h 30m (55m)
- PHX Phoenix 55m
-
- M
- -
- -
- T
- F
- -
- -
-
06:20 - 09:45SAN - DEN11:35 - 15:00DEN - ORD
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06:20 (SAN)San Diego International Airport11:35 (DEN)Denver Intl Airport
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09:45 (DEN)Denver Intl Airport15:00 (ORD)Chicago O'Hare International Airport
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(WN 1790)Boeing 737 700 (WN 2315)Boeing 737 700 - 6h 40m (1h 50m)
- DEN Denver 1h 50m
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- -
- T
- W
- -
- -
- -
- -
-
06:20 - 07:45SAN - LAS09:25 - 15:20LAS - ORD
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06:20 (SAN)San Diego International Airport09:25 (LAS)Las Vegas McCarran International Airport
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07:45 (LAS)Las Vegas McCarran International Airport15:20 (ORD)Chicago O'Hare International Airport
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(WN 440)Boeing 737 700 (WN 914)Boeing 737 Max 8 Passenger - 7h (1h 40m)
- LAS Las Vegas 1h 40m
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- M
- -
- -
- T
- F
- -
- -
-
06:20 - 09:45SAN - DEN12:10 - 15:25DEN - MDW
-
06:20 (SAN)San Diego International Airport12:10 (DEN)Denver Intl Airport
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09:45 (DEN)Denver Intl Airport15:25 (MDW)Chicago Midway Airport
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(WN 1790)Boeing 737 700 (WN 2107)Boeing 737 700 - 7h 05m (2h 25m)
- DEN Denver 2h 25m
-
- -
- T
- W
- -
- -
- -
- -
-
06:30 - 14:35SAN - BWI15:35 - 16:35BWI - MDW
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06:30 (SAN)San Diego International Airport15:35 (BWI)Baltimore Washington International Airport
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14:35 (BWI)Baltimore Washington International Airport16:35 (MDW)Chicago Midway Airport
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(WN 1101)Boeing 737 Max 8 Passenger (WN 2136)Boeing 737 Max 8 Passenger - 8h 05m (1h)
- BWI Baltimore 1h
-
- -
- -
- -
- -
- -
- -
- S
-
06:40 - 11:40SAN - DAL12:40 - 15:00DAL - ORD
-
06:40 (SAN)San Diego International Airport12:40 (DAL)Dallas/Fort Worth Love Field Airport
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11:40 (DAL)Dallas/Fort Worth Love Field Airport15:00 (ORD)Chicago O'Hare International Airport
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(WN 4783)Boeing 737 700 (WN 4903)Boeing 737 Max 8 Passenger - 6h 20m (1h)
- DAL Dallas 1h
-
- -
- -
- -
- -
- -
- -
- S
-
06:40 - 08:05SAN - LAS09:25 - 15:20LAS - ORD
-
06:40 (SAN)San Diego International Airport09:25 (LAS)Las Vegas McCarran International Airport
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08:05 (LAS)Las Vegas McCarran International Airport15:20 (ORD)Chicago O'Hare International Airport
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(WN 426)Boeing 737 700 (WN 914)Boeing 737 Max 8 Passenger - 6h 40m (1h 20m)
- LAS Las Vegas 1h 20m
-
- -
- T
- W
- -
- -
- -
- -
-
06:40 - 08:05SAN - LAS10:00 - 15:30LAS - MDW
-
06:40 (SAN)San Diego International Airport10:00 (LAS)Las Vegas McCarran International Airport
-
08:05 (LAS)Las Vegas McCarran International Airport15:30 (MDW)Chicago Midway Airport
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(WN 426)Boeing 737 700 (WN 636)Boeing 737 Max 8 Passenger - 6h 50m (1h 55m)
- LAS Las Vegas 1h 55m
-
- -
- T
- W
- -
- -
- -
- -
-
06:40 - 11:30SAN - AUS13:05 - 15:35AUS - MDW
-
06:40 (SAN)San Diego International Airport13:05 (AUS)Austin-Bergstrom International Airport
-
11:30 (AUS)Austin-Bergstrom International Airport15:35 (MDW)Chicago Midway Airport
-
(WN 5904)Boeing 737 800 (WN 2496)Boeing 737 Max 8 Passenger - 6h 55m (1h 35m)
- AUS Austin 1h 35m
-
- -
- -
- -
- -
- -
- -
- S
-
06:40 - 11:35SAN - AUS13:15 - 15:45AUS - MDW
-
06:40 (SAN)San Diego International Airport13:15 (AUS)Austin-Bergstrom International Airport
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11:35 (AUS)Austin-Bergstrom International Airport15:45 (MDW)Chicago Midway Airport
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(WN 5904)Boeing 737 800 (WN 2496)Boeing 737 Max 8 Passenger - 7h 05m (1h 40m)
- AUS Austin 1h 40m
-
- M
- -
- -
- T
- F
- -
- -
-
06:40 - 11:40SAN - DAL14:00 - 16:10DAL - MDW
-
06:40 (SAN)San Diego International Airport14:00 (DAL)Dallas/Fort Worth Love Field Airport
-
11:40 (DAL)Dallas/Fort Worth Love Field Airport16:10 (MDW)Chicago Midway Airport
-
(WN 4783)Boeing 737 700 (WN 473)Boeing 737 Max 8 Passenger - 7h 30m (2h 20m)
- DAL Dallas 2h 20m
-
- -
- -
- -
- -
- -
- -
- S
-
06:40 - 11:30SAN - AUS13:45 - 16:25AUS - ORD
-
06:40 (SAN)San Diego International Airport13:45 (AUS)Austin-Bergstrom International Airport
-
11:30 (AUS)Austin-Bergstrom International Airport16:25 (ORD)Chicago O'Hare International Airport
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(WN 5904)Boeing 737 800 (WN 3621)Boeing 737 800 - 7h 45m (2h 15m)
- AUS Austin 2h 15m
-
- -
- -
- -
- -
- -
- -
- S
-
06:40 - 08:05SAN - LAS11:30 - 17:05LAS - MDW
-
06:40 (SAN)San Diego International Airport11:30 (LAS)Las Vegas McCarran International Airport
-
08:05 (LAS)Las Vegas McCarran International Airport17:05 (MDW)Chicago Midway Airport
-
(WN 426)Boeing 737 700 (WN 2075)Boeing 737 Max 8 Passenger - 8h 25m (3h 25m)
- LAS Las Vegas 3h 25m
-
- -
- T
- W
- -
- -
- -
- -
-
06:40 - 11:30SAN - AUS14:30 - 17:05AUS - MDW
-
06:40 (SAN)San Diego International Airport14:30 (AUS)Austin-Bergstrom International Airport
-
11:30 (AUS)Austin-Bergstrom International Airport17:05 (MDW)Chicago Midway Airport
-
(WN 5904)Boeing 737 800 (WN 2496)Boeing 737 800 - 8h 25m (3h)
- AUS Austin 3h
-
- -
- T
- W
- -
- -
- -
- -
-
06:45 - 08:10SAN - LAS11:05 - 16:35LAS - MDW
-
06:45 (SAN)San Diego International Airport11:05 (LAS)Las Vegas McCarran International Airport
-
08:10 (LAS)Las Vegas McCarran International Airport16:35 (MDW)Chicago Midway Airport
-
(WN 426)Boeing 737 800 (WN 2075)Boeing 737 800 - 7h 50m (2h 55m)
- LAS Las Vegas 2h 55m
-
- -
- -
- -
- -
- -
- S
- -
-
06:50 - 10:10SAN - DEN12:10 - 15:35DEN - ORD
-
06:50 (SAN)San Diego International Airport12:10 (DEN)Denver Intl Airport
-
10:10 (DEN)Denver Intl Airport15:35 (ORD)Chicago O'Hare International Airport
-
(WN 1790)Boeing 737 700 (WN 4161)Boeing 737 700 - 6h 45m (2h)
- DEN Denver 2h
-
- M
- -
- -
- T
- F
- -
- -
-
06:50 - 11:35SAN - AUS13:25 - 16:00AUS - MDW
-
06:50 (SAN)San Diego International Airport13:25 (AUS)Austin-Bergstrom International Airport
-
11:35 (AUS)Austin-Bergstrom International Airport16:00 (MDW)Chicago Midway Airport
-
(WN 2597)Boeing 737 700 (WN 2496)Boeing 737 800 - 7h 10m (1h 50m)
- AUS Austin 1h 50m
-
- -
- -
- -
- -
- -
- S
- -
-
07:00 - 15:00SAN - BWI16:00 - 17:00BWI - MDW
-
07:00 (SAN)San Diego International Airport16:00 (BWI)Baltimore Washington International Airport
-
15:00 (BWI)Baltimore Washington International Airport17:00 (MDW)Chicago Midway Airport
-
(WN 1101)Boeing 737 Max 8 Passenger (WN 2136)Boeing 737 800 - 8h (1h)
- BWI Baltimore 1h
-
- -
- -
- -
- -
- -
- S
- -
-
07:00 - 14:55SAN - BWI16:40 - 17:45BWI - MDW
-
07:00 (SAN)San Diego International Airport16:40 (BWI)Baltimore Washington International Airport
-
14:55 (BWI)Baltimore Washington International Airport17:45 (MDW)Chicago Midway Airport
-
(WN 1101)Boeing 737 700 (WN 2136)Boeing 737 800 - 8h 45m (1h 45m)
- BWI Baltimore 1h 45m
-
- -
- T
- W
- -
- -
- -
- -
-
07:05 - 12:10SAN - HOU14:15 - 16:40HOU - MDW
-
07:05 (SAN)San Diego International Airport14:15 (HOU)Houston Hobby Airport
-
12:10 (HOU)Houston Hobby Airport16:40 (MDW)Chicago Midway Airport
-
(WN 5659)Boeing 737 800 (WN 3970)Boeing 737 700 - 7h 35m (2h 05m)
- HOU Houston 2h 05m
-
- -
- -
- -
- -
- -
- S
- -
-
07:10 - 12:05SAN - DAL12:50 - 15:00DAL - MDW
-
07:10 (SAN)San Diego International Airport12:50 (DAL)Dallas/Fort Worth Love Field Airport
-
12:05 (DAL)Dallas/Fort Worth Love Field Airport15:00 (MDW)Chicago Midway Airport
-
(WN 4783)Boeing 737 700 (WN 473)Boeing 737 Max 8 Passenger - 5h 50m (45m)
- DAL Dallas 45m
-
- -
- -
- -
- -
- -
- S
- -
-
07:15 - 08:30SAN - PHX09:35 - 14:50PHX - MDW
-
07:15 (SAN)San Diego International Airport09:35 (PHX)Phoenix Sky Harbor Intl Airport
-
08:30 (PHX)Phoenix Sky Harbor Intl Airport14:50 (MDW)Chicago Midway Airport
-
(WN 2358)Boeing 737 700 (WN 3198)Boeing 737 Max 8 Passenger - 5h 35m (1h 05m)
- PHX Phoenix 1h 05m
-
- M
- -
- -
- T
- F
- -
- -
-
07:15 - 08:35SAN - PHX09:50 - 15:05PHX - MDW
-
07:15 (SAN)San Diego International Airport09:50 (PHX)Phoenix Sky Harbor Intl Airport
-
08:35 (PHX)Phoenix Sky Harbor Intl Airport15:05 (MDW)Chicago Midway Airport
-
(WN 2358)Boeing 737 700 (WN 3198)Boeing 737 800 - 5h 50m (1h 15m)
- PHX Phoenix 1h 15m
-
- -
- T
- W
- -
- -
- -
- -
-
07:15 - 08:30SAN - PHX11:35 - 17:00PHX - ORD
-
07:15 (SAN)San Diego International Airport11:35 (PHX)Phoenix Sky Harbor Intl Airport
-
08:30 (PHX)Phoenix Sky Harbor Intl Airport17:00 (ORD)Chicago O'Hare International Airport
-
(WN 2358)Boeing 737 700 (WN 5265)Boeing 737 Max 8 Passenger - 7h 45m (3h 05m)
- PHX Phoenix 3h 05m
-
- M
- -
- -
- T
- F
- -
- -
-
07:15 - 08:35SAN - PHX11:35 - 17:00PHX - ORD
-
07:15 (SAN)San Diego International Airport11:35 (PHX)Phoenix Sky Harbor Intl Airport
-
08:35 (PHX)Phoenix Sky Harbor Intl Airport17:00 (ORD)Chicago O'Hare International Airport
-
(WN 2358)Boeing 737 700 (WN 5265)Boeing 737 Max 8 Passenger - 7h 45m (3h)
- PHX Phoenix 3h
-
- -
- T
- W
- -
- -
- -
- -
-
07:15 - 08:35SAN - PHX12:00 - 17:15PHX - MDW
-
07:15 (SAN)San Diego International Airport12:00 (PHX)Phoenix Sky Harbor Intl Airport
-
08:35 (PHX)Phoenix Sky Harbor Intl Airport17:15 (MDW)Chicago Midway Airport
-
(WN 2358)Boeing 737 700 (WN 3199)Boeing 737 Max 8 Passenger - 8h (3h 25m)
- PHX Phoenix 3h 25m
-
- -
- T
- W
- -
- -
- -
- -
-
07:20 - 08:40SAN - PHX09:40 - 15:00PHX - MDW
-
07:20 (SAN)San Diego International Airport09:40 (PHX)Phoenix Sky Harbor Intl Airport
-
08:40 (PHX)Phoenix Sky Harbor Intl Airport15:00 (MDW)Chicago Midway Airport
-
(WN 2358)Boeing 737 800 (WN 3198)Boeing 737 800 - 5h 40m (1h)
- PHX Phoenix 1h
-
- -
- -
- -
- -
- -
- -
- S
-
07:20 - 08:40SAN - PHX09:40 - 16:05PHX - MDW
-
07:20 (SAN)San Diego International Airport09:40 (PHX)Phoenix Sky Harbor Intl Airport
-
08:40 (PHX)Phoenix Sky Harbor Intl Airport16:05 (MDW)Chicago Midway Airport
-
(WN 2358)Boeing 737 800 (WN 4813)Boeing 737 700 - 6h 45m (1h)
- PHX Phoenix 1h
-
- -
- -
- -
- -
- -
- -
- S
-
12:40 - 16:15ABQ - MDW07:20 - 08:40SAN - PHX
-
12:40 (ABQ)Albuquerque Airport07:20 (SAN)San Diego International Airport
-
16:15 (MDW)Chicago Midway Airport08:40 (PHX)Phoenix Sky Harbor Intl Airport
-
(WN 3144)Boeing 737 800 (WN 2358)Boeing 737 800 - 6h 55m (1h 55m)
- MDW Chicago 1h 55m
-
- -
- -
- -
- -
- -
- -
- S
-
07:20 - 08:40SAN - PHX11:50 - 17:05PHX - MDW
-
07:20 (SAN)San Diego International Airport11:50 (PHX)Phoenix Sky Harbor Intl Airport
-
08:40 (PHX)Phoenix Sky Harbor Intl Airport17:05 (MDW)Chicago Midway Airport
-
(WN 2358)Boeing 737 800 (WN 3199)Boeing 737 800 - 7h 45m (3h 10m)
- PHX Phoenix 3h 10m
-
- -
- -
- -
- -
- -
- -
- S
-
07:30 - 09:05SAN - SMF11:05 - 17:00SMF - MDW
-
07:30 (SAN)San Diego International Airport11:05 (SMF)Sacramento International Airport
-
09:05 (SMF)Sacramento International Airport17:00 (MDW)Chicago Midway Airport
-
(WN 6045)Boeing 737 Max 8 Passenger (WN 5605)Boeing 737 Max 8 Passenger - 7h 30m (2h)
- SMF Sacramento 2h
-
- -
- T
- W
- -
- -
- -
- -
-
07:35 - 10:55SAN - DEN12:35 - 15:50DEN - MDW
-
07:35 (SAN)San Diego International Airport12:35 (DEN)Denver Intl Airport
-
10:55 (DEN)Denver Intl Airport15:50 (MDW)Chicago Midway Airport
-
(WN 1790)Boeing 737 Max 8 Passenger (WN 2107)Boeing 737 800 - 6h 15m (1h 40m)
- DEN Denver 1h 40m
-
- -
- -
- -
- -
- -
- -
- S
-
07:35 - 08:50SAN - PHX09:35 - 16:10PHX - MDW
-
07:35 (SAN)San Diego International Airport09:35 (PHX)Phoenix Sky Harbor Intl Airport
-
08:50 (PHX)Phoenix Sky Harbor Intl Airport16:10 (MDW)Chicago Midway Airport
-
(WN 2358)Boeing 737 Max 8 Passenger (WN 298)Boeing 737 800 - 6h 35m (45m)
- PHX Phoenix 45m
-
- -
- -
- -
- -
- -
- S
- -
-
07:35 - 08:50SAN - PHX11:10 - 16:25PHX - MDW
-
07:35 (SAN)San Diego International Airport11:10 (PHX)Phoenix Sky Harbor Intl Airport
-
08:50 (PHX)Phoenix Sky Harbor Intl Airport16:25 (MDW)Chicago Midway Airport
-
(WN 2358)Boeing 737 Max 8 Passenger (WN 3199)Boeing 737 Max 8 Passenger - 6h 50m (2h 20m)
- PHX Phoenix 2h 20m
-
- -
- -
- -
- -
- -
- S
- -
-
07:35 - 10:55SAN - DEN13:30 - 17:00DEN - ORD
-
07:35 (SAN)San Diego International Airport13:30 (DEN)Denver Intl Airport
-
10:55 (DEN)Denver Intl Airport17:00 (ORD)Chicago O'Hare International Airport
-
(WN 1790)Boeing 737 Max 8 Passenger (WN 1130)Boeing 737 800 - 7h 25m (2h 35m)
- DEN Denver 2h 35m
-
- -
- -
- -
- -
- -
- -
- S
-
07:35 - 10:55SAN - DEN14:05 - 17:25DEN - MDW
-
07:35 (SAN)San Diego International Airport14:05 (DEN)Denver Intl Airport
-
10:55 (DEN)Denver Intl Airport17:25 (MDW)Chicago Midway Airport
-
(WN 1790)Boeing 737 Max 8 Passenger (WN 1483)Boeing 737 Max 8 Passenger - 7h 50m (3h 10m)
- DEN Denver 3h 10m
-
- -
- -
- -
- -
- -
- -
- S
-
07:40 - 09:00SAN - LAS12:30 - 18:10LAS - MDW
-
07:40 (SAN)San Diego International Airport12:30 (LAS)Las Vegas McCarran International Airport
-
09:00 (LAS)Las Vegas McCarran International Airport18:10 (MDW)Chicago Midway Airport
-
(WN 191)Boeing 737 700 (WN 993)Boeing 737 Max 8 Passenger - 8h 30m (3h 30m)
- LAS Las Vegas 3h 30m
-
- M
- -
- -
- T
- F
- -
- -
-
07:50 - 11:15SAN - DEN12:05 - 15:25DEN - MDW
-
07:50 (SAN)San Diego International Airport12:05 (DEN)Denver Intl Airport
-
11:15 (DEN)Denver Intl Airport15:25 (MDW)Chicago Midway Airport
-
(WN 4161)Boeing 737 700 (WN 2107)Boeing 737 Max 8 Passenger - 5h 35m (50m)
- DEN Denver 50m
-
- -
- -
- -
- -
- -
- S
- -
-
07:50 - 12:45SAN - DAL14:45 - 16:55DAL - MDW
-
07:50 (SAN)San Diego International Airport14:45 (DAL)Dallas/Fort Worth Love Field Airport
-
12:45 (DAL)Dallas/Fort Worth Love Field Airport16:55 (MDW)Chicago Midway Airport
-
(WN 4783)Boeing 737 Max 8 Passenger (WN 5380)Boeing 737 Max 8 Passenger - 7h 05m (2h)
- DAL Dallas 2h
-
- -
- T
- W
- -
- -
- -
- -
-
07:55 - 13:35SAN - STL14:20 - 15:25STL - MDW
-
07:55 (SAN)San Diego International Airport14:20 (STL)St Louis Lambert Intl Airport
-
13:35 (STL)St Louis Lambert Intl Airport15:25 (MDW)Chicago Midway Airport
-
(WN 3497)Boeing 737 700 (WN 2732)Boeing 737 700 - 5h 30m (45m)
- STL Saint Louis 45m
-
- -
- -
- -
- -
- -
- -
- S
-
08:00 - 11:20SAN - DEN12:10 - 15:25DEN - MDW
-
08:00 (SAN)San Diego International Airport12:10 (DEN)Denver Intl Airport
-
11:20 (DEN)Denver Intl Airport15:25 (MDW)Chicago Midway Airport
-
(WN 4161)Boeing 737 700 (WN 2107)Boeing 737 700 - 5h 25m (50m)
- DEN Denver 50m
-
- -
- T
- W
- -
- -
- -
- -
-
08:00 - 11:20SAN - DEN14:25 - 17:55DEN - ORD
-
08:00 (SAN)San Diego International Airport14:25 (DEN)Denver Intl Airport
-
11:20 (DEN)Denver Intl Airport17:55 (ORD)Chicago O'Hare International Airport
-
(WN 4161)Boeing 737 700 (WN 3640)Boeing 737 Max 8 Passenger - 7h 55m (3h 05m)
- DEN Denver 3h 05m
-
- -
- T
- W
- -
- -
- -
- -
-
08:00 - 11:20SAN - DEN14:50 - 18:10DEN - MDW
-
08:00 (SAN)San Diego International Airport14:50 (DEN)Denver Intl Airport
-
11:20 (DEN)Denver Intl Airport18:10 (MDW)Chicago Midway Airport
-
(WN 4161)Boeing 737 700 (WN 698)Boeing 737 Max 8 Passenger - 8h 10m (3h 30m)
- DEN Denver 3h 30m
-
- -
- T
- W
- -
- -
- -
- -
-
08:05 - 13:15SAN - MCI15:15 - 16:35MCI - MDW
-
08:05 (SAN)San Diego International Airport15:15 (MCI)Kansas City International Airport
-
13:15 (MCI)Kansas City International Airport16:35 (MDW)Chicago Midway Airport
-
(WN 4163)Boeing 737 700 (WN 3408)Boeing 737 700 - 6h 30m (2h)
- MCI Kansas City 2h
-
- -
- -
- -
- -
- -
- -
- S
-
08:05 - 11:30SAN - DEN14:35 - 17:55DEN - MDW
-
08:05 (SAN)San Diego International Airport14:35 (DEN)Denver Intl Airport
-
11:30 (DEN)Denver Intl Airport17:55 (MDW)Chicago Midway Airport
-
(WN 4161)Boeing 737 700 (WN 698)Boeing 737 Max 8 Passenger - 7h 50m (3h 05m)
- DEN Denver 3h 05m
-
- M
- -
- -
- T
- F
- -
- -
-
08:20 - 09:40SAN - LAS11:30 - 17:05LAS - MDW
-
08:20 (SAN)San Diego International Airport11:30 (LAS)Las Vegas McCarran International Airport
-
09:40 (LAS)Las Vegas McCarran International Airport17:05 (MDW)Chicago Midway Airport
-
(WN 1817)Boeing 737 700 (WN 2075)Boeing 737 Max 8 Passenger - 6h 45m (1h 50m)
- LAS Las Vegas 1h 50m
-
- -
- T
- W
- -
- -
- -
- -
-
08:30 - 10:10SAN - SMF11:05 - 17:00SMF - MDW
-
08:30 (SAN)San Diego International Airport11:05 (SMF)Sacramento International Airport
-
10:10 (SMF)Sacramento International Airport17:00 (MDW)Chicago Midway Airport
-
(WN 3147)Boeing 737 700 (WN 5605)Boeing 737 Max 8 Passenger - 6h 30m (55m)
- SMF Sacramento 55m
-
- -
- T
- W
- -
- -
- -
- -
-
08:30 - 10:05SAN - SJC12:20 - 18:25SJC - MDW
-
08:30 (SAN)San Diego International Airport12:20 (SJC)San Jose International Airport
-
10:05 (SJC)San Jose International Airport18:25 (MDW)Chicago Midway Airport
-
(WN 4093)Boeing 737 700 (WN 5229)Boeing 737 Max 8 Passenger - 7h 55m (2h 15m)
- SJC San Jose 2h 15m
-
- M
- -
- -
- T
- F
- -
- -
-
08:30 - 10:10SAN - SMF12:40 - 18:35SMF - MDW
-
08:30 (SAN)San Diego International Airport12:40 (SMF)Sacramento International Airport
-
10:10 (SMF)Sacramento International Airport18:35 (MDW)Chicago Midway Airport
-
(WN 3147)Boeing 737 700 (WN 5605)Boeing 737 Max 8 Passenger - 8h 05m (2h 30m)
- SMF Sacramento 2h 30m
-
- M
- -
- -
- T
- F
- -
- -
-
08:35 - 09:50SAN - PHX11:35 - 17:00PHX - ORD
-
08:35 (SAN)San Diego International Airport11:35 (PHX)Phoenix Sky Harbor Intl Airport
-
09:50 (PHX)Phoenix Sky Harbor Intl Airport17:00 (ORD)Chicago O'Hare International Airport
-
(WN 6051)Boeing 737 700 (WN 5265)Boeing 737 Max 8 Passenger - 6h 25m (1h 45m)
- PHX Phoenix 1h 45m
-
- -
- T
- W
- -
- -
- -
- -
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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 American 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 17:35. 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.
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
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