Airlines with flights from San Diego to Chicago

There are three airlines with scheduled flights between SAN and MDW. Southwest is the only airline with non-stop flights from San Diego International Airport to Midway International Airport and the flight time is 3 hours and 55 minutes.

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Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 3 hours and 55 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 24 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
SAN
Direct
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN1184
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06:20
WN3513
06:30
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WN3430
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06:55
06:55
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06:35
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WN770
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06:45
06:45
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15:05
WN4443
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11:10
11:10
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10:10
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WN3137
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11:05
11:05
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WN4163
12:10
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WN3448
17:30
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WN657
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17:50
17:50
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WN257
22:40
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WN3431
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22:40
22:40
22:40
22:40
22:40
22:40
SHOW RETURN SCHEDULE
CHECK PRICES FOR SAN - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Phoenix with Southwest Airlines

  • Total flight time: 5h 15m - 10h 20m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 287 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
SAN
 
Via PHX
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN441
WN3221
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06:20
06:20
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WN3423
WN371
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06:20
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WN3447
WN4066
06:40
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WN1083
WN4663
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07:25
07:25
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WN3441
WN3221
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07:50
07:50
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WN3524
WN4066
08:00
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WN3441
WN4663
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08:15
WN3441
WN4503
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08:35
08:35
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WN4967
WN4978
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09:10
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WN3263
WN3329
09:45
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WN1502
WN4663
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09:55
WN3443
WN2012
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10:15
10:15
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WN428
WN4978
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12:20
12:20
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WN1140
WN4978
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13:45
13:45
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WN765
WN4085
13:50
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WN1140
WN1129
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13:50
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WN1140
WN2638
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13:50
WN4212
WN1129
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15:05
WN749
WN1129
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15:15
WN4453
WN1129
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15:30
15:30
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WN3526
WN3298
19:50
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WN1424
WN3224
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21:00
21:00
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WN3446
WN3224
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21:35
WN3527
WN3298
21:45
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SHOW RETURN SCHEDULE
CHECK PRICES FOR SAN - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Saint Louis with Southwest Airlines

  • Total flight time: 5h 15m - 11h 25m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 52 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
SAN
 
Via STL
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2631
WN3865
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08:30
08:30
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WN3471
WN3865
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12:15
12:15
12:25
12:25
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WN3471
WN2032
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12:35
WN3552
WN3957
13:30
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SHOW RETURN SCHEDULE
CHECK PRICES FOR SAN - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Kansas City with Southwest Airlines

  • Total flight time: 5h 15m - 9h 20m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 32 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
SAN
 
Via MCI
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN3151
WN2523
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11:05
11:05
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SHOW RETURN SCHEDULE
CHECK PRICES FOR SAN - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Denver with Southwest Airlines

  • Total flight time: 5h 25m - 10h 00m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 252 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
SAN
 
Via DEN
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN3274
WN4021
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06:20
WN1912
WN523
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06:35
06:35
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WN3411
WN1428
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06:45
06:45
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WN3411
WN450
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06:55
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WN3412
WN701
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08:15
WN1511
WN1110
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08:30
08:30
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WN1690
WN1110
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08:45
08:45
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WN4476
WN1110
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08:45
08:45
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WN330
WN1561
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09:00
09:00
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WN2406
WN1110
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09:05
09:05
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WN3494
WN1251
09:20
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WN3412
WN2613
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09:35
09:35
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WN3263
WN1603
09:45
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WN1768
WN1562
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09:50
WN1445
WN4717
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10:10
10:10
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WN3415
WN1561
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10:15
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WN3495
WN1251
10:35
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WN3415
WN1152
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10:50
WN2672
WN1563
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11:05
11:05
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WN2344
WN1563
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11:35
11:35
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WN297
WN1563
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11:40
11:40
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WN659
WN1563
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11:40
WN1991
WN1110
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11:45
11:45
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WN1133
WN1615
12:10
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WN3580
WN1563
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12:15
WN4839
WN3439
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12:50
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WN4139
WN1562
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12:55
WN3496
WN1604
13:20
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WN1435
WN1563
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13:40
13:40
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WN2059
WN1563
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13:50
13:50
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WN3414
WN1563
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15:15
15:15
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14:15
WN3497
WN1615
14:55
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SHOW RETURN SCHEDULE
CHECK PRICES FOR SAN - MDW

The timetable & schedule information was updated at 2026-04-21

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At Airlineinformation.com you can learn all about the airlines operating around the world together with their destinations and where they operate. You will get a transparent overview of airlines with scheduled flights between any two destinations with non-stop or 1-stop flights regardless of price or availability.
Flight data on this page was last updated on 2026-07-21
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