Airlines with flights from San Diego to Chicago

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.

Change direction

Choose airline

Schedules

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).
  • 14 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
SAN
Direct
MDW
 
Flight
Mon
Feb 3
Tue
Feb 4
Wed
Feb 5
Thu
Feb 6
Fri
Feb 7
Sat
Feb 8
Sun
Feb 9
WN3254
----
----
----
06:55
06:55
----
----
WN106
----
----
----
----
----
09:20
----
WN770
11:10
11:10
11:10
----
----
----
11:10
WN1167
----
----
----
----
----
14:35
----
WN1506
16:50
16:50
16:50
17:15
17:15
----
16:50
SHOW RETURN SCHEDULE
CHECK PRICES FOR SAN - MDW

The timetable & schedule information was updated at 2025-01-15

Via Las Vegas with Southwest Airlines

  • Total flight time: 5h 35m - 10h 25m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 36 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
SAN
 
Via LAS
 
MDW
 
Flight
Mon
Feb 3
Tue
Feb 4
Wed
Feb 5
Thu
Feb 6
Fri
Feb 7
Sat
Feb 8
Sun
Feb 9
WN1102
WN2756
06:45
06:45
06:45
06:30
06:30
----
06:45
WN3457
WN648
----
----
----
06:40
06:40
----
----
WN1102
WN4876
06:45
06:45
06:45
----
----
----
06:45
WN1102
WN2337
06:45
06:45
06:45
----
----
----
06:45
WN3095
WN2906
----
----
----
06:50
06:50
----
----
WN648
WN277
----
----
----
----
----
06:50
----
WN2834
WN1354
----
----
----
----
----
06:50
----
WN2834
WN715
----
----
----
----
----
06:50
----
WN1410
WN1036
07:10
07:10
07:10
----
----
----
07:10
WN1410
WN4165
07:10
07:10
07:10
----
----
----
----
WN932
WN1036
----
----
----
07:10
07:10
----
----
WN1243
WN2434
----
----
----
07:35
07:35
----
----
WN1243
WN3434
07:40
07:40
07:40
----
----
----
07:40
WN1243
WN4071
07:40
07:40
07:40
----
----
----
07:40
WN1108
WN2564
----
----
----
----
----
08:00
----
WN932
WN4165
08:05
08:05
08:05
----
----
----
----
WN1689
WN1533
----
----
----
08:15
08:15
----
----
WN1261
WN2497
08:25
08:25
08:25
08:15
08:15
----
08:25
WN1315
WN2564
08:15
08:15
08:15
----
----
----
08:15
WN1689
WN1036
----
----
----
08:15
08:15
----
----
WN1689
WN1277
----
----
----
08:15
08:15
----
----
WN2023
WN130
----
----
----
----
----
08:20
----
WN2737
WN948
----
----
----
08:45
08:45
----
----
WN1159
WN1253
----
----
----
----
----
08:45
----
WN3294
WN4514
----
----
----
08:50
08:50
----
----
WN1256
WN1036
----
----
----
08:55
08:55
----
----
WN1256
WN1277
----
----
----
08:55
08:55
----
----
WN1256
WN1533
----
----
----
08:55
08:55
----
----
WN1387
WN2912
----
----
----
09:00
09:00
----
----
WN2983
WN2497
----
----
----
09:15
09:15
----
----
WN2983
WN3423
----
----
----
09:15
09:15
----
----
WN2476
WN3784
09:40
09:40
09:40
----
----
----
09:40
WN671
WN4071
----
----
----
09:40
09:40
----
----
WN1277
WN1533
----
----
----
09:50
09:50
----
----
WN4315
WN419
10:00
10:00
10:00
----
----
----
10:00
WN949
WN2329
10:00
10:00
10:00
----
----
----
10:00
WN4315
WN130
10:00
10:00
10:00
----
----
----
----
WN4315
WN4514
10:00
10:00
10:00
----
----
----
10:00
WN909
WN3197
----
----
----
----
----
10:20
----
WN931
WN419
----
----
----
----
----
10:40
----
WN1416
WN3423
----
----
----
10:40
10:40
----
----
WN1486
WN4928
----
----
----
11:00
11:00
----
----
WN1052
WN340
11:20
11:20
11:20
----
----
----
----
WN1052
WN3150
11:20
11:20
11:20
----
----
----
11:20
WN3091
WN419
11:35
11:35
11:35
----
----
----
11:35
WN1355
WN1729
----
----
----
----
----
11:50
----
WN840
WN2054
----
----
----
11:50
11:50
----
----
WN840
WN3150
----
----
----
11:50
11:50
----
----
WN2817
WN419
----
----
----
12:00
12:00
----
----
WN1910
WN3423
12:10
12:10
12:10
----
----
----
12:10
WN3789
WN4372
----
----
----
12:15
12:15
----
----
WN3048
WN1647
----
----
----
12:50
12:50
----
----
WN2068
WN381
12:50
12:50
12:50
----
----
----
----
WN2560
WN1729
----
----
----
----
----
12:55
----
WN866
WN3197
----
----
----
----
----
13:00
----
WN875
WN2054
----
----
----
13:00
13:00
----
----
WN236
WN2054
13:05
13:05
13:05
----
----
----
13:05
WN197
WN298
----
----
----
13:15
13:15
----
----
WN3034
WN4758
----
----
----
----
----
----
13:20
WN3034
WN340
13:20
13:20
13:20
----
----
----
----
WN1416
WN2965
14:10
14:10
14:10
----
----
----
----
WN1416
WN1647
----
----
----
----
----
----
14:10
WN1352
WN1397
14:25
14:25
14:25
----
----
----
14:25
WN2180
WN1678
----
----
----
14:25
14:25
----
----
WN1988
WN869
----
----
----
----
----
14:40
----
WN432
WN4188
----
----
----
14:55
14:55
----
----
WN432
WN3960
----
----
----
14:55
14:55
----
----
WN581
WN1397
15:15
15:15
15:15
----
----
----
15:15
WN2433
WN2668
----
----
----
----
----
15:15
----
WN875
WN4188
15:20
15:20
15:20
----
----
----
15:40
WN2715
WN4104
----
----
----
15:30
15:30
----
----
WN489
WN1678
----
----
----
15:35
15:35
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR SAN - MDW

The timetable & schedule information was updated at 2025-01-15

Via Phoenix with Southwest Airlines

  • Total flight time: 5h 20m - 10h 10m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 34 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
SAN
 
Via PHX
 
MDW
 
Flight
Mon
Feb 3
Tue
Feb 4
Wed
Feb 5
Thu
Feb 6
Fri
Feb 7
Sat
Feb 8
Sun
Feb 9
WN1102
WN2756
06:45
06:45
06:45
06:30
06:30
----
06:45
WN3457
WN648
----
----
----
06:40
06:40
----
----
WN1102
WN4876
06:45
06:45
06:45
----
----
----
06:45
WN1102
WN2337
06:45
06:45
06:45
----
----
----
06:45
WN3095
WN2906
----
----
----
06:50
06:50
----
----
WN648
WN277
----
----
----
----
----
06:50
----
WN2834
WN1354
----
----
----
----
----
06:50
----
WN2834
WN715
----
----
----
----
----
06:50
----
WN1410
WN1036
07:10
07:10
07:10
----
----
----
07:10
WN1410
WN4165
07:10
07:10
07:10
----
----
----
----
WN932
WN1036
----
----
----
07:10
07:10
----
----
WN1243
WN2434
----
----
----
07:35
07:35
----
----
WN1243
WN3434
07:40
07:40
07:40
----
----
----
07:40
WN1243
WN4071
07:40
07:40
07:40
----
----
----
07:40
WN1108
WN2564
----
----
----
----
----
08:00
----
WN932
WN4165
08:05
08:05
08:05
----
----
----
----
WN1689
WN1533
----
----
----
08:15
08:15
----
----
WN1261
WN2497
08:25
08:25
08:25
08:15
08:15
----
08:25
WN1315
WN2564
08:15
08:15
08:15
----
----
----
08:15
WN1689
WN1036
----
----
----
08:15
08:15
----
----
WN1689
WN1277
----
----
----
08:15
08:15
----
----
WN2023
WN130
----
----
----
----
----
08:20
----
WN2737
WN948
----
----
----
08:45
08:45
----
----
WN1159
WN1253
----
----
----
----
----
08:45
----
WN3294
WN4514
----
----
----
08:50
08:50
----
----
WN1256
WN1036
----
----
----
08:55
08:55
----
----
WN1256
WN1277
----
----
----
08:55
08:55
----
----
WN1256
WN1533
----
----
----
08:55
08:55
----
----
WN1387
WN2912
----
----
----
09:00
09:00
----
----
WN2983
WN2497
----
----
----
09:15
09:15
----
----
WN2983
WN3423
----
----
----
09:15
09:15
----
----
WN2476
WN3784
09:40
09:40
09:40
----
----
----
09:40
WN671
WN4071
----
----
----
09:40
09:40
----
----
WN1277
WN1533
----
----
----
09:50
09:50
----
----
WN4315
WN419
10:00
10:00
10:00
----
----
----
10:00
WN949
WN2329
10:00
10:00
10:00
----
----
----
10:00
WN4315
WN130
10:00
10:00
10:00
----
----
----
----
WN4315
WN4514
10:00
10:00
10:00
----
----
----
10:00
WN909
WN3197
----
----
----
----
----
10:20
----
WN931
WN419
----
----
----
----
----
10:40
----
WN1416
WN3423
----
----
----
10:40
10:40
----
----
WN1486
WN4928
----
----
----
11:00
11:00
----
----
WN1052
WN340
11:20
11:20
11:20
----
----
----
----
WN1052
WN3150
11:20
11:20
11:20
----
----
----
11:20
WN3091
WN419
11:35
11:35
11:35
----
----
----
11:35
WN1355
WN1729
----
----
----
----
----
11:50
----
WN840
WN2054
----
----
----
11:50
11:50
----
----
WN840
WN3150
----
----
----
11:50
11:50
----
----
WN2817
WN419
----
----
----
12:00
12:00
----
----
WN1910
WN3423
12:10
12:10
12:10
----
----
----
12:10
WN3789
WN4372
----
----
----
12:15
12:15
----
----
WN3048
WN1647
----
----
----
12:50
12:50
----
----
WN2068
WN381
12:50
12:50
12:50
----
----
----
----
WN2560
WN1729
----
----
----
----
----
12:55
----
WN866
WN3197
----
----
----
----
----
13:00
----
WN875
WN2054
----
----
----
13:00
13:00
----
----
WN236
WN2054
13:05
13:05
13:05
----
----
----
13:05
WN197
WN298
----
----
----
13:15
13:15
----
----
WN3034
WN4758
----
----
----
----
----
----
13:20
WN3034
WN340
13:20
13:20
13:20
----
----
----
----
WN1416
WN2965
14:10
14:10
14:10
----
----
----
----
WN1416
WN1647
----
----
----
----
----
----
14:10
WN1352
WN1397
14:25
14:25
14:25
----
----
----
14:25
WN2180
WN1678
----
----
----
14:25
14:25
----
----
WN1988
WN869
----
----
----
----
----
14:40
----
WN432
WN4188
----
----
----
14:55
14:55
----
----
WN432
WN3960
----
----
----
14:55
14:55
----
----
WN581
WN1397
15:15
15:15
15:15
----
----
----
15:15
WN2433
WN2668
----
----
----
----
----
15:15
----
WN875
WN4188
15:20
15:20
15:20
----
----
----
15:40
WN2715
WN4104
----
----
----
15:30
15:30
----
----
WN489
WN1678
----
----
----
15:35
15:35
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR SAN - MDW

The timetable & schedule information was updated at 2025-01-15

Via Denver with Southwest Airlines

  • Total flight time: 5h 20m - 10h 05m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 28 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
SAN
 
Via DEN
 
MDW
 
Flight
Mon
Feb 3
Tue
Feb 4
Wed
Feb 5
Thu
Feb 6
Fri
Feb 7
Sat
Feb 8
Sun
Feb 9
WN1102
WN2756
06:45
06:45
06:45
06:30
06:30
----
06:45
WN3457
WN648
----
----
----
06:40
06:40
----
----
WN1102
WN4876
06:45
06:45
06:45
----
----
----
06:45
WN1102
WN2337
06:45
06:45
06:45
----
----
----
06:45
WN3095
WN2906
----
----
----
06:50
06:50
----
----
WN648
WN277
----
----
----
----
----
06:50
----
WN2834
WN1354
----
----
----
----
----
06:50
----
WN2834
WN715
----
----
----
----
----
06:50
----
WN1410
WN1036
07:10
07:10
07:10
----
----
----
07:10
WN1410
WN4165
07:10
07:10
07:10
----
----
----
----
WN932
WN1036
----
----
----
07:10
07:10
----
----
WN1243
WN2434
----
----
----
07:35
07:35
----
----
WN1243
WN3434
07:40
07:40
07:40
----
----
----
07:40
WN1243
WN4071
07:40
07:40
07:40
----
----
----
07:40
WN1108
WN2564
----
----
----
----
----
08:00
----
WN932
WN4165
08:05
08:05
08:05
----
----
----
----
WN1689
WN1533
----
----
----
08:15
08:15
----
----
WN1261
WN2497
08:25
08:25
08:25
08:15
08:15
----
08:25
WN1315
WN2564
08:15
08:15
08:15
----
----
----
08:15
WN1689
WN1036
----
----
----
08:15
08:15
----
----
WN1689
WN1277
----
----
----
08:15
08:15
----
----
WN2023
WN130
----
----
----
----
----
08:20
----
WN2737
WN948
----
----
----
08:45
08:45
----
----
WN1159
WN1253
----
----
----
----
----
08:45
----
WN3294
WN4514
----
----
----
08:50
08:50
----
----
WN1256
WN1036
----
----
----
08:55
08:55
----
----
WN1256
WN1277
----
----
----
08:55
08:55
----
----
WN1256
WN1533
----
----
----
08:55
08:55
----
----
WN1387
WN2912
----
----
----
09:00
09:00
----
----
WN2983
WN2497
----
----
----
09:15
09:15
----
----
WN2983
WN3423
----
----
----
09:15
09:15
----
----
WN2476
WN3784
09:40
09:40
09:40
----
----
----
09:40
WN671
WN4071
----
----
----
09:40
09:40
----
----
WN1277
WN1533
----
----
----
09:50
09:50
----
----
WN4315
WN419
10:00
10:00
10:00
----
----
----
10:00
WN949
WN2329
10:00
10:00
10:00
----
----
----
10:00
WN4315
WN130
10:00
10:00
10:00
----
----
----
----
WN4315
WN4514
10:00
10:00
10:00
----
----
----
10:00
WN909
WN3197
----
----
----
----
----
10:20
----
WN931
WN419
----
----
----
----
----
10:40
----
WN1416
WN3423
----
----
----
10:40
10:40
----
----
WN1486
WN4928
----
----
----
11:00
11:00
----
----
WN1052
WN340
11:20
11:20
11:20
----
----
----
----
WN1052
WN3150
11:20
11:20
11:20
----
----
----
11:20
WN3091
WN419
11:35
11:35
11:35
----
----
----
11:35
WN1355
WN1729
----
----
----
----
----
11:50
----
WN840
WN2054
----
----
----
11:50
11:50
----
----
WN840
WN3150
----
----
----
11:50
11:50
----
----
WN2817
WN419
----
----
----
12:00
12:00
----
----
WN1910
WN3423
12:10
12:10
12:10
----
----
----
12:10
WN3789
WN4372
----
----
----
12:15
12:15
----
----
WN3048
WN1647
----
----
----
12:50
12:50
----
----
WN2068
WN381
12:50
12:50
12:50
----
----
----
----
WN2560
WN1729
----
----
----
----
----
12:55
----
WN866
WN3197
----
----
----
----
----
13:00
----
WN875
WN2054
----
----
----
13:00
13:00
----
----
WN236
WN2054
13:05
13:05
13:05
----
----
----
13:05
WN197
WN298
----
----
----
13:15
13:15
----
----
WN3034
WN4758
----
----
----
----
----
----
13:20
WN3034
WN340
13:20
13:20
13:20
----
----
----
----
WN1416
WN2965
14:10
14:10
14:10
----
----
----
----
WN1416
WN1647
----
----
----
----
----
----
14:10
WN1352
WN1397
14:25
14:25
14:25
----
----
----
14:25
WN2180
WN1678
----
----
----
14:25
14:25
----
----
WN1988
WN869
----
----
----
----
----
14:40
----
WN432
WN4188
----
----
----
14:55
14:55
----
----
WN432
WN3960
----
----
----
14:55
14:55
----
----
WN581
WN1397
15:15
15:15
15:15
----
----
----
15:15
WN2433
WN2668
----
----
----
----
----
15:15
----
WN875
WN4188
15:20
15:20
15:20
----
----
----
15:40
WN2715
WN4104
----
----
----
15:30
15:30
----
----
WN489
WN1678
----
----
----
15:35
15:35
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR SAN - MDW

The timetable & schedule information was updated at 2025-01-15

Via Dallas with Southwest Airlines

  • Total flight time: 5h 50m - 11h 20m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 18 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
SAN
 
Via DAL
 
MDW
 
Flight
Mon
Feb 3
Tue
Feb 4
Wed
Feb 5
Thu
Feb 6
Fri
Feb 7
Sat
Feb 8
Sun
Feb 9
WN1102
WN2756
06:45
06:45
06:45
06:30
06:30
----
06:45
WN3457
WN648
----
----
----
06:40
06:40
----
----
WN1102
WN4876
06:45
06:45
06:45
----
----
----
06:45
WN1102
WN2337
06:45
06:45
06:45
----
----
----
06:45
WN3095
WN2906
----
----
----
06:50
06:50
----
----
WN648
WN277
----
----
----
----
----
06:50
----
WN2834
WN1354
----
----
----
----
----
06:50
----
WN2834
WN715
----
----
----
----
----
06:50
----
WN1410
WN1036
07:10
07:10
07:10
----
----
----
07:10
WN1410
WN4165
07:10
07:10
07:10
----
----
----
----
WN932
WN1036
----
----
----
07:10
07:10
----
----
WN1243
WN2434
----
----
----
07:35
07:35
----
----
WN1243
WN3434
07:40
07:40
07:40
----
----
----
07:40
WN1243
WN4071
07:40
07:40
07:40
----
----
----
07:40
WN1108
WN2564
----
----
----
----
----
08:00
----
WN932
WN4165
08:05
08:05
08:05
----
----
----
----
WN1689
WN1533
----
----
----
08:15
08:15
----
----
WN1261
WN2497
08:25
08:25
08:25
08:15
08:15
----
08:25
WN1315
WN2564
08:15
08:15
08:15
----
----
----
08:15
WN1689
WN1036
----
----
----
08:15
08:15
----
----
WN1689
WN1277
----
----
----
08:15
08:15
----
----
WN2023
WN130
----
----
----
----
----
08:20
----
WN2737
WN948
----
----
----
08:45
08:45
----
----
WN1159
WN1253
----
----
----
----
----
08:45
----
WN3294
WN4514
----
----
----
08:50
08:50
----
----
WN1256
WN1036
----
----
----
08:55
08:55
----
----
WN1256
WN1277
----
----
----
08:55
08:55
----
----
WN1256
WN1533
----
----
----
08:55
08:55
----
----
WN1387
WN2912
----
----
----
09:00
09:00
----
----
WN2983
WN2497
----
----
----
09:15
09:15
----
----
WN2983
WN3423
----
----
----
09:15
09:15
----
----
WN2476
WN3784
09:40
09:40
09:40
----
----
----
09:40
WN671
WN4071
----
----
----
09:40
09:40
----
----
WN1277
WN1533
----
----
----
09:50
09:50
----
----
WN4315
WN419
10:00
10:00
10:00
----
----
----
10:00
WN949
WN2329
10:00
10:00
10:00
----
----
----
10:00
WN4315
WN130
10:00
10:00
10:00
----
----
----
----
WN4315
WN4514
10:00
10:00
10:00
----
----
----
10:00
WN909
WN3197
----
----
----
----
----
10:20
----
WN931
WN419
----
----
----
----
----
10:40
----
WN1416
WN3423
----
----
----
10:40
10:40
----
----
WN1486
WN4928
----
----
----
11:00
11:00
----
----
WN1052
WN340
11:20
11:20
11:20
----
----
----
----
WN1052
WN3150
11:20
11:20
11:20
----
----
----
11:20
WN3091
WN419
11:35
11:35
11:35
----
----
----
11:35
WN1355
WN1729
----
----
----
----
----
11:50
----
WN840
WN2054
----
----
----
11:50
11:50
----
----
WN840
WN3150
----
----
----
11:50
11:50
----
----
WN2817
WN419
----
----
----
12:00
12:00
----
----
WN1910
WN3423
12:10
12:10
12:10
----
----
----
12:10
WN3789
WN4372
----
----
----
12:15
12:15
----
----
WN3048
WN1647
----
----
----
12:50
12:50
----
----
WN2068
WN381
12:50
12:50
12:50
----
----
----
----
WN2560
WN1729
----
----
----
----
----
12:55
----
WN866
WN3197
----
----
----
----
----
13:00
----
WN875
WN2054
----
----
----
13:00
13:00
----
----
WN236
WN2054
13:05
13:05
13:05
----
----
----
13:05
WN197
WN298
----
----
----
13:15
13:15
----
----
WN3034
WN4758
----
----
----
----
----
----
13:20
WN3034
WN340
13:20
13:20
13:20
----
----
----
----
WN1416
WN2965
14:10
14:10
14:10
----
----
----
----
WN1416
WN1647
----
----
----
----
----
----
14:10
WN1352
WN1397
14:25
14:25
14:25
----
----
----
14:25
WN2180
WN1678
----
----
----
14:25
14:25
----
----
WN1988
WN869
----
----
----
----
----
14:40
----
WN432
WN4188
----
----
----
14:55
14:55
----
----
WN432
WN3960
----
----
----
14:55
14:55
----
----
WN581
WN1397
15:15
15:15
15:15
----
----
----
15:15
WN2433
WN2668
----
----
----
----
----
15:15
----
WN875
WN4188
15:20
15:20
15:20
----
----
----
15:40
WN2715
WN4104
----
----
----
15:30
15:30
----
----
WN489
WN1678
----
----
----
15:35
15:35
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR SAN - MDW

The timetable & schedule information was updated at 2025-01-15

Change direction

Staying up-to-date with the airlines

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.
© 2025 Westcoast Digital