Airlines with flights from San Antonio to Chicago
There are two airlines with scheduled flights between SAT and MDW. Southwest is the only airline with non-stop flights from San Antonio International to Midway International Airport and the flight time is 2 hours and 35 minutes.
There are two airlines with scheduled flights between SAT and MDW. Southwest is the only airline with non-stop flights from San Antonio International to Midway International Airport and the flight time is 2 hours and 35 minutes. Choose airline
Direct
Non-stop
2h 35min
Via Kansas City
3h 55min
Via Dallas
4h 0min
Via Houston
4h 0min
Via Saint Louis
4h 10min
Via New Orleans
4h 20min
Via Nashville
4h 25min
Via Atlanta
5h 6min
Via Atlanta
5h 10min
Via Minneapolis
5h 21min
Via Detroit
5h 41min
Via Omaha
7h 45min
NEW
Via Columbus
6h 35min
Via Indianapolis
6h 55min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 2 hours and 35 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
14 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 PassengerBoeing 737-800 (winglets) Passenger/BBJ2
SAT
Direct
MDW
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
WN586
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----
----
05:00
05:00
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----
WN3583
06:25
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----
----
----
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----
WN3790
----
----
----
----
----
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07:00
WN3946
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09:25
09:25
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----
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WN3503
----
14:35
14:50
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----
11:10
14:30
WN245
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----
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14:15
14:15
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WN3584
15:20
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----
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
Via Kansas City with Southwest Airlines
-
Total flight time: 3h 55m - 6h 30m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
32 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 PassengerBoeing 737-800 (winglets) Passenger/BBJ2
SAT
Via MCI
MDW
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
WN346
WN4829
WN4829
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----
----
----
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07:35
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WN1432
WN2572
WN2572
11:00
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----
----
----
----
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WN3500
WN2525
WN2525
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11:40
11:40
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WN3285
WN2525
WN2525
----
----
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12:05
12:05
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WN1926
WN2525
WN2525
----
----
----
----
----
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13:20
The timetable & schedule information was updated at 2026-04-21
Via Dallas with Southwest Airlines
-
Total flight time: 4h 00m - 8h 15m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
235 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 PassengerBoeing 737-800 (winglets) Passenger/BBJ2
SAT
Via DAL
MDW
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
WN4512
WN4386
WN4386
05:40
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----
----
----
----
----
WN4477
WN586
WN586
----
----
----
----
----
05:40
----
WN1895
WN694
WN694
----
06:40
06:40
----
----
----
----
WN1356
WN1357
WN1357
06:45
----
----
----
----
----
----
WN1908
WN1324
WN1324
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----
----
07:10
07:10
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WN4809
WN1328
WN1328
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----
----
----
----
----
07:25
WN346
WN586
WN586
----
----
----
----
----
07:35
----
WN2275
WN3613
WN3613
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09:20
09:20
----
----
----
----
WN2275
WN855
WN855
----
----
----
----
----
09:45
----
WN1346
WN4201
WN4201
----
----
----
----
----
----
10:05
WN1809
WN22
WN22
----
----
----
11:10
11:10
----
----
WN4470
WN1326
WN1326
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11:30
11:30
----
----
----
----
WN4195
WN1358
WN1358
11:45
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----
----
----
----
----
WN1624
WN1327
WN1327
----
----
----
12:20
12:20
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----
WN4470
WN1327
WN1327
----
----
----
----
----
12:55
----
WN1353
WN1327
WN1327
----
13:30
13:30
----
----
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----
WN609
WN1327
WN1327
----
----
----
----
----
14:30
----
WN4782
WN1327
WN1327
----
15:15
15:15
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----
----
----
WN609
WN1326
WN1326
----
----
----
----
----
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15:20
WN1377
WN1312
WN1312
----
----
----
----
----
----
17:40
WN172
WN668
WN668
----
----
----
17:40
17:40
----
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WN1338
WN1359
WN1359
20:05
----
----
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
Via Houston with Southwest Airlines
-
Total flight time: 4h 00m - 9h 25m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
119 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 PassengerBoeing 737-800 (winglets) Passenger/BBJ2
SAT
Via HOU
MDW
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
WN4543
WN1294
WN1294
05:30
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----
----
----
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WN3188
WN265
WN265
----
----
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06:00
06:00
----
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WN3188
WN256
WN256
----
07:35
07:35
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----
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06:30
WN342
WN4769
WN4769
----
----
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08:35
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WN3498
WN1966
WN1966
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----
----
----
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12:20
WN3566
WN2029
WN2029
12:50
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WN3197
WN1966
WN1966
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12:55
12:55
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WN804
WN2771
WN2771
----
----
----
----
----
15:40
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WN3573
WN2044
WN2044
18:30
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----
----
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WN1944
WN2278
WN2278
----
----
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19:30
The timetable & schedule information was updated at 2026-04-21
Via Saint Louis with Southwest Airlines
-
Total flight time: 4h 10m - 7h 30m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
63 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 PassengerBoeing 737-800 (winglets) Passenger/BBJ2
SAT
Via STL
MDW
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
WN1430
WN3862
WN3862
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07:10
07:10
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----
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WN2209
WN3861
WN3861
----
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07:25
07:25
----
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WN2340
WN2032
WN2032
----
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----
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----
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15:50
WN3590
WN3957
WN3957
16:50
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----
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The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Delta