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).
  • 28 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
SAN
Direct
MDW
 
Flight
Mon
Jun 15
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Jun 16
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Jun 17
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Jun 18
Fri
Jun 19
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Jun 20
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Jun 21
WN3513
06:30
06:20
06:20
06:30
06:30
06:30
06:20
WN1677
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10:45
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WN4163
12:10
10:50
10:50
12:10
12:10
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WN3448
17:30
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17:30
17:30
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15:40
WN257
22:40
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22:40
22:40
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WN354
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22:40
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WN560
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22:40
WN840
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22:40
22:40
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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 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 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
SAN
 
Via PHX
 
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN425
WN554
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06:40
06:40
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WN3447
WN4066
06:40
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06:40
06:40
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WN3447
WN284
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06:40
WN248
WN3296
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07:50
07:50
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WN3524
WN4066
08:00
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08:00
08:00
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08:55
WN1807
WN4066
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08:35
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WN3263
WN4066
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08:40
08:40
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WN3263
WN3329
09:45
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09:45
09:45
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WN3818
WN2340
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10:10
WN5065
WN2162
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11:30
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WN765
WN770
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12:10
WN765
WN3297
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13:15
13:15
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WN765
WN4085
13:50
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13:50
13:50
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WN3525
WN3190
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15:05
15:05
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WN3523
WN2521
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16:25
16:25
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WN3403
WN3298
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19:40
19:40
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WN3526
WN3298
19:50
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19:50
19:50
20:10
19:50
WN3404
WN3298
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20:45
20:45
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WN3527
WN3298
21:45
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21:45
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 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
SAN
 
Via STL
 
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN2231
WN2832
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06:35
WN765
WN3957
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12:10
WN3552
WN3957
13:30
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13:30
13:30
12:20
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WN2328
WN3957
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12:25
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WN3677
WN3957
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13:20
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 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
SAN
 
Via MCI
 
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN1788
WN2572
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----
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06:35
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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 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
SAN
 
Via DEN
 
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN3493
WN284
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06:20
06:20
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WN3493
WN1524
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06:35
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WN3370
WN1601
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06:40
WN2354
WN1603
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07:05
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WN3494
WN1601
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07:45
WN3494
WN284
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07:45
07:45
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WN2763
WN1524
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07:50
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WN3494
WN1251
09:20
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09:20
09:20
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WN3263
WN1603
09:45
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09:45
09:45
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WN915
WN1603
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10:25
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WN3495
WN1251
10:35
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10:35
10:35
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WN3495
WN1604
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10:55
10:55
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11:05
WN1133
WN1615
12:10
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12:10
12:10
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WN3496
WN1604
13:20
13:10
13:10
13:20
13:20
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12:45
WN3496
WN223
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14:00
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WN3497
WN1614
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14:50
WN3497
WN1615
14:55
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14:55
14:55
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WN4151
WN1615
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16:50
SHOW RETURN SCHEDULE
CHECK PRICES FOR SAN - MDW

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

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Flight data on this page was last updated on 2026-06-02
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