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
Starts 04/06
Via Columbus
6h 35min
Starts 04/06
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).
-
18 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)
SAT
Direct
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN3583
06:25
09:20
09:20
06:25
06:25
09:25
06:50
WN3584
15:20
14:00
14:00
15:20
15:20
14:15
----
WN3361
----
----
----
----
----
----
15:25
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 737MAX 8 PassengerBoeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)
SAT
Via MCI
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN1432
WN2572
WN2572
11:00
----
----
11:00
11:00
----
----
WN3446
WN2953
WN2953
----
11:25
11:25
----
----
----
----
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 737MAX 8 PassengerBoeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)
SAT
Via DAL
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN4512
WN2744
WN2744
----
----
----
----
----
----
05:20
WN1349
WN1198
WN1198
----
05:30
05:30
----
----
----
----
WN4512
WN4386
WN4386
05:40
----
----
05:40
05:40
----
----
WN1356
WN1357
WN1357
06:45
----
----
06:45
06:45
----
----
WN1356
WN1517
WN1517
----
07:15
07:15
----
----
----
----
WN1502
WN8
WN8
----
----
----
----
----
07:50
----
WN4512
WN1357
WN1357
----
08:20
08:20
----
----
----
----
WN4195
WN1358
WN1358
11:45
12:00
12:00
11:45
11:45
----
11:00
WN2664
WN1006
WN1006
----
----
----
----
----
11:40
----
WN3433
WN41
WN41
----
13:20
13:20
----
----
----
----
WN1356
WN41
WN41
----
----
----
----
----
14:00
----
WN3434
WN987
WN987
----
14:40
14:40
----
----
----
----
WN3014
WN107
WN107
----
----
----
----
----
----
15:05
WN2154
WN1329
WN1329
----
----
----
----
----
----
17:45
WN1338
WN1359
WN1359
20:05
18:25
18:25
20:05
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 737MAX 8 PassengerBoeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)
SAT
Via HOU
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN4543
WN1294
WN1294
05:30
----
----
05:30
05:30
----
----
WN4545
WN993
WN993
----
----
----
----
----
----
05:40
WN4392
WN8
WN8
----
----
----
----
----
05:50
----
WN4392
WN2902
WN2902
----
06:10
06:10
----
----
----
----
WN1849
WN823
WN823
----
----
----
----
----
08:20
----
WN3566
WN425
WN425
----
----
----
----
----
----
09:45
WN3566
WN2029
WN2029
12:50
----
----
12:50
12:50
----
----
WN3566
WN2042
WN2042
----
12:55
12:55
----
----
----
----
WN1850
WN2044
WN2044
----
----
----
----
----
17:10
----
WN3573
WN2044
WN2044
18:30
17:30
17:30
18:30
18:30
----
----
WN2789
WN2044
WN2044
----
----
----
----
----
----
18:15
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 737MAX 8 PassengerBoeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)
SAT
Via STL
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN4809
WN1373
WN1373
----
07:25
07:25
----
----
----
----
WN3590
WN3957
WN3957
16:50
----
----
16:50
16:50
----
----
The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Delta