Airlines with flights from Chicago to San Antonio
There are two airlines with scheduled flights between MDW and SAT. Southwest is the only airline with non-stop flights from Midway International Airport to San Antonio International and the flight time is 2 hours and 50 minutes.
There are two airlines with scheduled flights between MDW and SAT. Southwest is the only airline with non-stop flights from Midway International Airport to San Antonio International and the flight time is 2 hours and 50 minutes. Choose airline
Direct
Non-stop
2h 50min
Via Dallas
4h 10min
Via Kansas City
4h 10min
Via Houston
4h 15min
Via Saint Louis
4h 25min
Via Nashville
4h 35min
Via Atlanta
5h 4min
Via Atlanta
5h 5min
Via Detroit
5h 13min
Via Minneapolis
5h 14min
Via New Orleans
5h 25min
NEW
Starts 04/10
Via Columbus
8h 0min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 2 hours and 50 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
14 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
MDW
Direct
SAT
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
WN559
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10:10
10:10
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13:50
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WN436
----
----
----
----
----
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10:20
WN2570
10:35
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----
----
----
----
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WN1009
----
----
----
11:05
11:05
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WN2819
----
20:30
20:30
----
----
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20:40
WN267
----
----
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20:35
20:35
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WN3229
21:25
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----
----
----
----
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The timetable & schedule information was updated at 2026-04-21
Via Dallas with Southwest Airlines
-
Total flight time: 4h 10m - 8h 50m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
178 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
MDW
Via DAL
SAT
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
WN1377
WN2617
WN2617
05:00
----
----
----
----
----
----
WN1005
WN482
WN482
----
----
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05:15
05:15
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----
WN2706
WN1513
WN1513
----
06:00
06:00
----
----
----
----
WN4025
WN1362
WN1362
----
----
----
----
----
----
06:05
WN3796
WN2617
WN2617
06:40
----
----
----
----
----
----
WN199
WN845
WN845
----
----
----
----
----
06:45
----
WN199
WN1362
WN1362
----
----
----
----
----
----
07:15
WN2707
WN4884
WN4884
----
----
----
07:25
07:25
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----
WN406
WN2397
WN2397
----
----
----
----
----
----
08:00
WN199
WN2539
WN2539
----
08:20
08:20
----
----
----
----
WN2412
WN2397
WN2397
----
----
----
----
----
----
09:20
WN1321
WN1400
WN1400
10:00
----
----
----
----
----
----
WN856
WN1944
WN1944
----
----
----
----
----
10:05
----
WN2707
WN1944
WN1944
----
----
----
----
----
10:15
----
WN409
WN1513
WN1513
----
----
----
----
----
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10:25
WN2844
WN754
WN754
----
10:30
10:30
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----
----
----
WN1152
WN1719
WN1719
----
----
----
11:00
11:00
----
----
WN1148
WN754
WN754
----
11:10
11:10
----
----
----
----
WN2757
WN1401
WN1401
12:20
----
----
----
----
----
----
WN2709
WN1719
WN1719
----
----
----
12:30
12:30
----
----
WN2708
WN1513
WN1513
----
----
----
----
----
----
12:30
WN1108
WN4511
WN4511
----
----
----
13:40
13:40
----
----
WN496
WN4415
WN4415
14:05
----
----
----
----
----
----
WN1271
WN382
WN382
----
----
----
----
----
14:15
----
WN1356
WN174
WN174
----
15:10
15:10
----
----
----
----
WN2709
WN4303
WN4303
----
----
----
----
----
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15:50
WN2758
WN4415
WN4415
16:20
----
----
----
----
----
----
WN2711
WN4511
WN4511
----
----
----
16:30
16:30
----
----
WN2711
WN1361
WN1361
----
17:15
17:15
----
----
----
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WN2961
WN1404
WN1404
18:15
----
----
----
----
----
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The timetable & schedule information was updated at 2026-04-21
Via Kansas City with Southwest Airlines
-
Total flight time: 4h 10m - 7h 40m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
37 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
MDW
Via MCI
SAT
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
WN2754
WN2801
WN2801
----
----
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07:30
07:30
----
----
WN1702
WN2583
WN2583
10:20
----
----
----
----
----
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WN2754
WN2732
WN2732
----
----
----
----
----
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11:30
WN2810
WN2583
WN2583
12:05
----
----
----
----
----
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WN875
WN2314
WN2314
----
14:45
14:45
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
Via Houston with Southwest Airlines
-
Total flight time: 4h 15m - 8h 50m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
131 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
MDW
Via HOU
SAT
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
WN2781
WN1432
WN1432
05:00
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----
----
----
----
----
WN2731
WN165
WN165
----
----
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05:55
05:55
----
----
WN3295
WN4589
WN4589
----
----
----
----
----
07:20
----
WN3950
WN813
WN813
----
07:50
07:50
----
----
----
----
WN356
WN2074
WN2074
08:05
----
----
----
----
----
----
WN680
WN2074
WN2074
10:00
----
----
----
----
----
----
WN2824
WN2074
WN2074
10:05
----
----
----
----
----
----
WN2733
WN2455
WN2455
----
----
----
10:05
10:05
----
----
WN2783
WN2074
WN2074
10:10
----
----
----
----
----
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WN4258
WN4589
WN4589
----
10:10
10:10
----
----
----
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WN4709
WN4589
WN4589
----
10:30
10:30
----
----
----
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WN1637
WN1377
WN1377
----
----
----
----
----
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11:10
WN2820
WN1581
WN1581
----
----
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13:05
13:05
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WN2733
WN3599
WN3599
----
17:15
17:15
----
----
----
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WN4709
WN1581
WN1581
----
----
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17:30
17:30
----
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WN2785
WN4451
WN4451
17:40
----
----
----
----
----
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WN2733
WN287
WN287
----
----
----
----
----
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17:45
WN1431
WN4451
WN4451
19:15
----
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----
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----
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The timetable & schedule information was updated at 2026-04-21
Via Saint Louis with Southwest Airlines
-
Total flight time: 4h 25m - 7h 55m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
28 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
MDW
Via STL
SAT
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
WN126
WN4166
WN4166
----
16:40
16:40
----
----
----
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WN4254
WN4390
WN4390
----
----
----
----
----
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17:50
WN4254
WN4166
WN4166
----
----
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17:50
17:50
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The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Delta