Airlines with flights from Houston to Chicago

There are two airlines with scheduled flights between HOU and MDW. Southwest is the only airline with non-stop flights from Hobby Airport to Midway International Airport and the flight time is 2 hours and 25 minutes.

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Choose airline

Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 2 hours and 25 minutes
  • Low-cost airline
  • Houston and Chicago are both Southwest Airlines focus cities.
  • 43 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
HOU
Direct
MDW
 
Flight
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Aug 3
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Aug 5
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WN1156
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05:00
05:00
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WN149
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06:50
06:50
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07:00
05:40
WN2039
06:25
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WN265
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16:45
16:45
07:20
07:20
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18:15
WN1294
08:10
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WN256
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09:40
09:40
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08:25
WN398
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10:30
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WN1019
11:20
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WN1988
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11:55
WN2041
13:30
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WN1964
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14:20
14:20
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WN1966
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14:45
14:45
17:45
17:45
15:15
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WN111
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14:50
WN158
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15:50
15:50
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WN2042
16:40
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WN2043
18:50
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WN2771
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19:55
19:55
19:40
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WN2044
20:35
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WN2278
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20:50
20:50
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21:50
SHOW RETURN SCHEDULE
CHECK PRICES FOR HOU - MDW

The timetable & schedule information was updated at 2026-04-22

Southwest Airlines

Via Saint Louis with Southwest Airlines

  • Total flight time: 3h 45m - 8h 00m.
  • Low-cost airline
  • Houston and Chicago are both Southwest Airlines focus cities.
  • 118 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
HOU
 
Via STL
 
MDW
 
Flight
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Aug 3
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Aug 9
WN2019
WN3861
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07:20
07:20
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WN2019
WN3862
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07:35
07:35
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WN2019
WN2052
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08:10
WN2084
WN556
10:40
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WN2303
WN3862
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11:05
11:05
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WN5064
WN2289
15:00
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WN2022
WN2032
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15:50
WN2022
WN3865
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15:55
15:55
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WN2144
WN3865
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16:05
16:05
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WN4724
WN3957
17:10
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WN2697
WN3865
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17:55
17:55
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SHOW RETURN SCHEDULE
CHECK PRICES FOR HOU - MDW

The timetable & schedule information was updated at 2026-04-22

Southwest Airlines

Via Oklahoma City with Southwest Airlines

  • Total flight time: 3h 50m - 8h 20m.
  • Low-cost airline
  • Houston and Chicago are both Southwest Airlines focus cities.
  • 27 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
HOU
 
Via OKC
 
MDW
 
Flight
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Aug 3
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Aug 8
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Aug 9
WN3589
WN4807
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08:40
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SHOW RETURN SCHEDULE
CHECK PRICES FOR HOU - MDW

The timetable & schedule information was updated at 2026-04-22

Southwest Airlines

Via Dallas with Southwest Airlines

  • Total flight time: 4h 00m - 8h 55m.
  • Low-cost airline
  • Houston and Chicago are both Southwest Airlines focus cities.
  • 206 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
HOU
 
Via DAL
 
MDW
 
Flight
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Aug 3
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WN1636
WN586
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06:00
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WN1636
WN1324
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06:00
06:00
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WN2
WN1328
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06:45
WN4
WN1324
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07:00
07:00
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WN4
WN694
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07:00
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WN4
WN1357
07:00
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WN6
WN1328
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07:40
WN8
WN1324
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08:00
08:00
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WN8
WN1357
08:00
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WN8
WN855
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WN4201
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WN10
WN1328
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WN12
WN855
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WN14
WN22
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WN3613
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WN20
WN3613
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WN22
WN1358
11:30
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WN22
WN1326
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11:30
11:30
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WN22
WN4201
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11:50
WN26
WN1326
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12:30
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WN28
WN1327
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WN30
WN4503
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WN30
WN36
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WN32
WN1327
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14:00
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WN34
WN1327
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14:40
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WN36
WN1225
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WN38
WN370
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WN40
WN107
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WN40
WN1225
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16:00
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WN1377
WN1312
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16:05
WN42
WN370
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16:30
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WN42
WN1312
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WN44
WN668
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WN46
WN107
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WN48
WN668
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18:00
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WN52
WN1359
19:00
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WN54
WN1359
20:30
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SHOW RETURN SCHEDULE
CHECK PRICES FOR HOU - MDW

The timetable & schedule information was updated at 2026-04-22

Southwest Airlines

Via Kansas City with Southwest Airlines

  • Total flight time: 4h 00m - 8h 10m.
  • Low-cost airline
  • Houston and Chicago are both Southwest Airlines focus cities.
  • 66 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
HOU
 
Via MCI
 
MDW
 
Flight
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Aug 3
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WN1037
WN2571
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WN978
WN2523
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08:05
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WN540
WN4829
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08:10
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WN2484
WN4829
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WN1432
WN2572
09:25
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WN2666
WN2522
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09:40
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WN2025
WN2525
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10:25
WN4795
WN2029
12:00
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WN2666
WN3473
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14:40
14:40
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WN3709
WN2604
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15:00
SHOW RETURN SCHEDULE
CHECK PRICES FOR HOU - MDW

The timetable & schedule information was updated at 2026-04-22

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At Airlineinformation.com you can learn all about the airlines operating around the world together with their destinations and where they operate. You will get a transparent overview of airlines with scheduled flights between any two destinations with non-stop or 1-stop flights regardless of price or availability.
Flight data on this page was last updated on 2026-07-21
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