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.

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Schedules

Southwest Airlines

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).
  • 16 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
MDW
Direct
SAT
 
Flight
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Jun 15
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Jun 21
WN1279
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10:10
WN1437
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10:25
10:25
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WN2570
10:35
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10:35
10:35
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WN224
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10:55
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WN3229
21:25
21:00
21:00
21:25
21:25
20:30
21:40
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SAT

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

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 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
MDW
 
Via DAL
 
SAT
 
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Jun 15
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WN690
WN1725
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05:00
WN1377
WN2617
05:00
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05:00
05:00
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WN2661
WN738
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05:05
05:05
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WN1370
WN738
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06:30
06:30
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WN3796
WN2617
06:40
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06:40
06:40
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WN2253
WN864
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07:25
WN1267
WN1401
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07:45
07:45
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WN163
WN3940
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08:50
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WN1321
WN1400
10:00
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10:00
10:00
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WN1702
WN1402
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10:10
10:10
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WN1331
WN1402
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11:30
11:30
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WN1401
WN2086
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11:35
WN2757
WN1401
12:20
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12:20
12:20
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WN488
WN2086
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13:40
WN2757
WN2758
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13:55
13:55
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WN496
WN4415
14:05
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14:05
14:05
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WN938
WN2808
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14:55
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WN1184
WN113
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15:40
WN1363
WN113
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16:05
WN2758
WN4415
16:20
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16:20
16:20
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WN496
WN113
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16:45
WN59
WN2617
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18:05
18:05
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WN2961
WN1404
18:15
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18:15
18:15
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SAT

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

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 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
MDW
 
Via MCI
 
SAT
 
Flight
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Jun 15
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Jun 19
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Jun 20
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Jun 21
WN4407
WN2552
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10:05
10:05
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WN1702
WN2583
10:20
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10:20
10:20
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WN2810
WN2583
12:05
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12:05
12:05
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----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SAT

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

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 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
MDW
 
Via HOU
 
SAT
 
Flight
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Jun 15
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Jun 20
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Jun 21
WN2781
WN1432
05:00
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05:00
05:00
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WN991
WN1714
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06:55
WN1772
WN2421
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07:05
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WN4497
WN1432
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07:10
07:10
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WN1180
WN4030
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07:40
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WN356
WN2074
08:05
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08:05
08:05
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WN680
WN2074
10:00
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10:00
10:00
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WN2824
WN2074
10:05
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10:05
10:05
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WN2783
WN2074
10:10
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10:10
10:10
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WN1301
WN4030
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10:35
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WN1514
WN4451
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15:25
WN2785
WN4451
17:40
16:15
16:15
17:40
17:40
17:05
18:10
WN3743
WN4451
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17:40
WN1431
WN4451
19:15
17:50
17:50
19:15
19:15
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SAT

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

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 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
MDW
 
Via STL
 
SAT
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
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Jun 18
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Jun 19
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Jun 20
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Jun 21
WN2902
WN2363
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13:10
WN103
WN3979
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14:35
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WN2904
WN3979
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17:10
17:10
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----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SAT

The timetable & schedule information was updated at 2026-04-21

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Flight data on this page was last updated on 2026-06-02
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