Airlines with flights from Chicago to San Diego
There are three airlines with scheduled flights between MDW and SAN. Southwest is the only airline with non-stop flights from Midway International Airport to San Diego International Airport and the flight time is 4 hours and 25 minutes.
There are three airlines with scheduled flights between MDW and SAN. Southwest is the only airline with non-stop flights from Midway International Airport to San Diego International Airport and the flight time is 4 hours and 25 minutes. Choose airline
Direct
Non-stop
4h 25min
Via Phoenix
5h 25min
Via Kansas City
5h 25min
Via Denver
5h 40min
Via Las Vegas
5h 45min
Via Dallas
5h 45min
Via Saint Louis
5h 45min
Via Indianapolis
5h 50min
Via Salt Lake City
6h 0min
Via Omaha
6h 0min
Via Austin
6h 5min
Via Minneapolis
6h 6min
Via Nashville
6h 15min
Via Detroit
6h 38min
Via Reno
6h 40min
Via Albuquerque
6h 45min
Via Dallas
8h 47min
Via Milwaukee
5h 50min
Via Colorado Springs
6h 30min
Via El Paso
6h 0min
NEW
Starts 06/08
Via Boise
7h 20min
NEW
Starts 06/08
Via Bozeman
7h 25min
NEW
Starts 09/08
Via Louisville
8h 5min
Starts 01/10
Via Tucson
6h 15min
NEW
Starts 03/10
Via Tulsa
7h 45min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 4 hours and 25 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
24 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
MDW
Direct
SAN
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN3103
05:45
----
----
----
----
----
----
WN1887
----
----
----
----
----
----
06:10
WN2814
----
10:05
10:05
06:15
06:15
10:00
10:35
WN4648
10:00
----
----
----
----
----
----
WN2815
----
----
----
10:15
10:15
----
----
WN363
----
----
----
----
----
14:05
----
WN2883
14:15
----
----
----
----
----
----
WN518
----
----
----
14:50
14:50
----
----
WN2816
----
15:05
15:05
----
----
----
----
WN4802
----
20:25
20:25
20:45
20:45
18:05
----
WN3355
----
----
----
----
----
----
20:25
WN2884
21:10
----
----
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
Via Phoenix with Southwest Airlines
-
Total flight time: 5h 25m - 10h 30m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
245 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
MDW
Via PHX
SAN
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2858
WN3321
WN3321
05:20
----
----
----
----
----
----
WN2793
WN548
WN548
----
----
----
----
----
----
05:40
WN270
WN548
WN548
----
----
----
05:40
05:40
----
----
WN2793
WN393
WN393
----
----
----
----
----
05:40
----
WN1138
WN456
WN456
----
----
----
----
----
----
07:10
WN564
WN4868
WN4868
----
----
----
07:10
07:10
----
----
WN2520
WN3322
WN3322
07:10
----
----
----
----
----
----
WN447
WN1017
WN1017
----
----
----
08:00
08:00
----
----
WN3016
WN2328
WN2328
08:40
----
----
----
----
----
----
WN2150
WN3248
WN3248
----
----
----
09:05
09:05
----
----
WN2150
WN428
WN428
----
----
----
----
----
----
09:10
WN188
WN366
WN366
----
09:25
09:25
----
----
----
----
WN4935
WN2431
WN2431
----
----
----
----
----
10:00
----
WN4084
WN3251
WN3251
----
10:10
10:10
----
----
----
----
WN2838
WN3251
WN3251
----
10:10
10:10
----
----
----
----
WN2984
WN897
WN897
10:10
----
----
----
----
----
----
WN1683
WN420
WN420
----
----
----
----
----
----
10:40
WN1181
WN4371
WN4371
----
11:10
11:10
----
----
----
----
WN4189
WN897
WN897
11:20
----
----
----
----
----
----
WN1230
WN3017
WN3017
12:15
----
----
----
----
----
----
WN4113
WN420
WN420
----
----
----
----
----
----
12:35
WN4249
WN3250
WN3250
----
----
----
----
----
12:40
----
WN2327
WN4372
WN4372
----
----
----
13:50
13:50
----
----
WN4249
WN3107
WN3107
----
13:55
13:55
----
----
----
----
WN268
WN2571
WN2571
----
----
----
----
----
14:40
----
WN965
WN3107
WN3107
----
15:15
15:15
----
----
----
----
WN2861
WN2580
WN2580
16:35
----
----
----
----
----
----
WN2316
WN4373
WN4373
----
----
----
16:55
16:55
----
----
WN268
WN4373
WN4373
----
----
----
----
----
----
17:15
WN454
WN4373
WN4373
----
17:20
17:20
----
----
----
----
WN324
WN4373
WN4373
----
----
----
18:15
18:15
----
----
WN2862
WN3426
WN3426
18:40
----
----
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
Via Kansas City with Southwest Airlines
-
Total flight time: 5h 25m - 10h 20m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
37 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
MDW
Via MCI
SAN
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2755
WN2313
WN2313
----
08:55
08:55
----
----
----
----
WN615
WN254
WN254
----
----
----
----
----
10:30
----
WN615
WN2313
WN2313
----
10:40
10:40
----
----
----
----
WN4407
WN4457
WN4457
14:10
----
----
----
----
----
----
WN2812
WN4457
WN4457
16:05
----
----
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
Via Denver with Southwest Airlines
-
Total flight time: 5h 40m - 10h 10m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
188 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
MDW
Via DEN
SAN
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2989
WN1699
WN1699
05:15
----
----
----
----
----
----
WN2717
WN2094
WN2094
----
----
----
----
----
----
06:30
WN2717
WN1657
WN1657
----
06:40
06:40
----
----
06:50
----
WN2765
WN1700
WN1700
06:45
----
----
----
----
----
----
WN136
WN653
WN653
----
----
----
----
----
----
07:55
WN314
WN1658
WN1658
----
08:55
08:55
----
----
----
----
WN2717
WN1255
WN1255
----
----
----
09:20
09:20
----
----
WN400
WN653
WN653
----
----
----
----
----
----
09:30
WN2654
WN3503
WN3503
09:55
----
----
----
----
----
----
WN271
WN1655
WN1655
----
----
----
----
----
10:00
----
WN3539
WN1658
WN1658
----
10:05
10:05
----
----
----
----
WN4571
WN1658
WN1658
----
----
----
----
----
----
10:10
WN1652
WN1658
WN1658
----
----
----
----
----
10:15
----
WN2719
WN1658
WN1658
----
12:00
12:00
----
----
----
----
WN2719
WN1062
WN1062
----
----
----
12:15
12:15
----
----
WN2719
WN269
WN269
----
----
----
----
----
----
12:25
WN4450
WN1703
WN1703
13:10
----
----
----
----
----
----
WN1893
WN1703
WN1703
13:15
----
----
----
----
----
----
WN2718
WN1658
WN1658
----
----
----
----
----
----
13:40
WN102
WN1659
WN1659
----
----
----
----
----
14:05
----
WN2721
WN385
WN385
----
----
----
14:05
14:05
----
----
WN1271
WN4022
WN4022
----
----
----
----
----
14:15
----
WN2768
WN4160
WN4160
14:30
----
----
----
----
----
----
WN267
WN1405
WN1405
----
----
----
----
----
----
14:40
WN655
WN4022
WN4022
----
----
----
16:25
16:25
----
----
WN2721
WN1405
WN1405
----
----
----
----
----
----
16:45
WN163
WN4022
WN4022
----
----
----
17:00
17:00
----
----
WN2721
WN4022
WN4022
----
18:00
18:00
----
----
17:05
----
WN1497
WN1704
WN1704
18:00
----
----
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
Via Las Vegas with Southwest Airlines
-
Total flight time: 5h 45m - 11h 30m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
225 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
MDW
Via LAS
SAN
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2740
WN554
WN554
----
----
----
----
----
----
05:25
WN1182
WN347
WN347
06:30
----
----
----
----
----
----
WN2723
WN1604
WN1604
----
----
----
06:40
06:40
----
----
WN2740
WN4926
WN4926
----
06:50
06:50
----
----
06:55
----
WN2741
WN2240
WN2240
----
----
----
----
----
----
06:55
WN347
WN2272
WN2272
07:30
----
----
----
----
----
----
WN4079
WN2269
WN2269
----
08:35
08:35
----
----
----
----
WN2741
WN4237
WN4237
----
08:35
08:35
----
----
----
----
WN776
WN2059
WN2059
----
----
----
08:50
08:50
----
----
WN1793
WN471
WN471
----
----
----
----
----
----
09:00
WN2794
WN2272
WN2272
09:10
----
----
----
----
----
----
WN2825
WN2268
WN2268
----
----
----
----
----
10:00
----
WN1321
WN3620
WN3620
10:00
----
----
----
----
----
----
WN2104
WN1771
WN1771
10:00
----
----
----
----
----
----
WN4874
WN2268
WN2268
----
----
----
10:05
10:05
----
----
WN398
WN2268
WN2268
----
----
----
10:05
10:05
----
----
WN3086
WN2268
WN2268
----
----
----
10:05
10:05
----
----
WN1771
WN3620
WN3620
10:10
----
----
----
----
----
----
WN1685
WN2269
WN2269
----
10:10
10:10
----
----
----
----
WN2707
WN2268
WN2268
----
----
----
----
----
10:15
----
WN2783
WN2269
WN2269
----
10:15
10:15
----
----
----
----
WN2668
WN1423
WN1423
----
----
----
----
----
----
10:15
WN1731
WN1423
WN1423
----
----
----
----
----
----
10:15
WN332
WN818
WN818
----
----
----
----
----
----
10:15
WN2099
WN2268
WN2268
----
----
----
10:15
10:15
----
----
WN2723
WN2269
WN2269
----
----
----
----
----
10:20
----
WN578
WN4237
WN4237
----
10:20
10:20
----
----
----
----
WN4874
WN818
WN818
----
----
----
----
----
----
10:25
WN3086
WN2269
WN2269
----
10:30
10:30
----
----
----
----
WN2742
WN2268
WN2268
----
----
----
11:10
11:10
----
----
WN4233
WN818
WN818
----
----
----
----
----
----
12:15
WN351
WN4635
WN4635
----
----
----
----
----
----
12:20
WN2795
WN1288
WN1288
13:40
----
----
----
----
----
----
WN3523
WN4635
WN4635
----
14:10
14:10
----
----
----
----
WN4233
WN4308
WN4308
----
----
----
16:00
16:00
----
----
WN2742
WN4635
WN4635
----
----
----
----
----
16:05
----
WN2742
WN369
WN369
----
16:45
16:45
----
----
----
----
WN2797
WN1227
WN1227
16:55
----
----
----
----
----
----
WN3957
WN138
WN138
----
----
----
----
----
----
17:40
WN2844
WN2871
WN2871
18:25
----
----
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
Via Minneapolis with Delta
Via Dallas with Frontier