Airlines with flights from Chicago to Houston

There are two airlines with scheduled flights between MDW and HOU. Southwest is the only airline with non-stop flights from Midway International Airport to Hobby Airport and the flight time is 2 hours and 35 minutes.

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Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 2 hours and 35 minutes
  • Low-cost airline
  • Chicago and Houston are both Southwest Airlines focus cities.
  • 49 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
Direct
HOU
 
Flight
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Jun 15
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Jun 17
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Jun 19
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Jun 20
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Jun 21
WN2781
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05:05
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WN4497
06:40
07:10
07:10
06:40
06:40
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WN991
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06:55
WN1001
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07:05
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WN2783
10:10
10:15
10:15
10:10
10:10
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WN1301
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10:35
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WN1674
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10:40
WN709
11:35
12:00
12:00
11:35
11:35
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WN2714
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12:35
WN5054
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13:10
13:10
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WN2785
17:40
16:15
16:15
17:40
17:40
17:05
18:10
WN1431
19:15
17:50
17:50
19:15
19:15
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WN2625
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20:25
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WN2787
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21:00
21:00
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WN954
21:40
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21:40
21:40
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21:40
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - HOU

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

Southwest Airlines

Via Saint Louis with Southwest Airlines

  • Total flight time: 3h 50m - 7h 35m.
  • Low-cost airline
  • Chicago and Houston are both Southwest Airlines focus cities.
  • 67 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
 
Via STL
 
HOU
 
Flight
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Jun 15
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Jun 16
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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
WN2900
WN1642
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06:30
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WN2901
WN4752
11:00
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11:00
11:00
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10:05
WN103
WN507
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14:35
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WN2903
WN770
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14:35
14:35
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WN2903
WN3988
14:45
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14:45
14:45
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WN2904
WN4617
18:00
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18:00
18:00
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WN1646
WN4617
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18:30
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - HOU

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

Southwest Airlines

Via Dallas with Southwest Airlines

  • Total flight time: 4h 00m - 8h 45m.
  • Low-cost airline
  • Chicago and Houston are both Southwest Airlines focus cities.
  • 205 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
 
Via DAL
 
HOU
 
Flight
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Jun 15
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Jun 16
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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
WN1377
WN7
05:00
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05:00
05:00
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WN690
WN3
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05:00
WN2661
WN7
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05:05
05:05
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WN1370
WN11
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06:30
06:30
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WN1321
WN15
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06:30
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WN3796
WN23
06:40
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06:40
06:40
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WN2253
WN19
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07:25
WN1267
WN25
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07:45
07:45
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WN163
WN19
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08:50
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WN3790
WN5079
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09:55
WN1321
WN29
10:00
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10:00
10:00
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WN1702
WN37
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10:10
10:10
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WN1331
WN37
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11:30
11:30
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WN1401
WN49
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11:35
WN2757
WN37
12:20
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12:20
12:20
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WN488
WN49
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13:40
WN2757
WN45
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13:55
13:55
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WN496
WN57
14:05
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14:05
14:05
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WN938
WN51
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14:55
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WN2758
WN53
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15:20
15:20
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WN1184
WN57
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15:40
WN1363
WN57
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16:05
WN2758
WN57
16:20
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16:20
16:20
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WN2961
WN63
18:15
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18:15
18:15
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - HOU

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

Southwest Airlines

Via Nashville with Southwest Airlines

  • Total flight time: 4h 05m - 8h 40m.
  • Low-cost airline
  • Chicago and Houston are both Southwest Airlines focus cities.
  • 143 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
 
Via BNA
 
HOU
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
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Jun 21
WN1337
WN550
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07:55
WN1775
WN533
07:55
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07:55
07:55
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08:30
WN2733
WN777
11:20
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11:20
11:20
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WN2733
WN533
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11:50
11:50
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WN3869
WN2040
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15:10
15:10
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WN1257
WN534
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15:30
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WN3614
WN534
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16:40
WN3869
WN534
17:05
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17:05
17:05
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WN1073
WN4474
18:40
17:20
17:20
18:40
18:40
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18:35
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - HOU

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

Southwest Airlines

Via Kansas City with Southwest Airlines

  • Total flight time: 4h 10m - 8h 05m.
  • Low-cost airline
  • Chicago and Houston are both Southwest Airlines focus cities.
  • 58 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
 
Via MCI
 
HOU
 
Flight
Mon
Jun 15
Tue
Jun 16
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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
WN2933
WN25
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07:50
07:50
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WN489
WN2555
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07:50
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WN1695
WN3395
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08:00
WN2808
WN2555
08:00
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08:00
08:00
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WN4407
WN2555
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11:50
WN103
WN2556
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14:35
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WN427
WN3977
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14:45
14:45
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WN4407
WN2556
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15:25
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WN2812
WN2556
16:05
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16:05
16:05
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WN766
WN3977
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16:15
16:15
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - HOU

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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