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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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.
  • 51 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
HOU
Direct
MDW
 
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
WN2038
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05:00
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WN1573
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05:10
WN2039
06:25
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06:25
06:25
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WN993
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07:25
WN1294
08:10
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08:10
08:10
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WN2902
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08:15
08:15
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WN670
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08:30
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WN2763
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11:30
11:30
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WN2041
13:30
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13:30
13:30
14:20
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WN2042
16:40
14:35
14:35
16:40
16:40
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15:15
WN5052
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16:30
16:30
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WN41
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18:20
18:20
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18:45
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WN2043
18:50
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18:50
18:50
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WN4944
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19:10
WN2044
20:35
21:25
21:25
20:35
20:35
20:45
21:20
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 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
HOU
 
Via STL
 
MDW
 
Flight
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Jun 15
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Jun 16
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Jun 18
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Jun 19
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Jun 20
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Jun 21
WN3662
WN1373
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07:35
07:35
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WN2084
WN556
10:40
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10:40
10:40
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11:55
WN1643
WN556
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11:05
11:05
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WN2524
WN2468
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12:20
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WN1031
WN3957
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14:20
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WN654
WN3957
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15:00
15:00
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WN3711
WN3957
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17:05
WN4724
WN3957
17:10
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17:10
17:10
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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 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
HOU
 
Via OKC
 
MDW
 
Flight
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Jun 15
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Jun 16
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Jun 19
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Jun 20
Sun
Jun 21
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 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
HOU
 
Via DAL
 
MDW
 
Flight
Mon
Jun 15
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Jun 16
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Jun 17
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Jun 18
Fri
Jun 19
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Jun 20
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Jun 21
WN121
WN2744
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05:35
WN1636
WN1198
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06:00
06:00
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WN4
WN1517
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07:00
07:00
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WN4
WN1357
07:00
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07:00
07:00
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WN8
WN1357
08:00
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08:00
08:00
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WN10
WN1357
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08:30
08:30
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WN14
WN1357
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09:30
09:30
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WN16
WN2664
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10:25
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WN20
WN1358
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11:00
11:00
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WN22
WN1358
11:30
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11:30
11:30
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WN22
WN1006
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11:50
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WN26
WN1358
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12:30
12:30
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WN26
WN1359
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12:30
WN30
WN36
13:30
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13:30
13:30
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WN38
WN987
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15:30
15:30
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WN40
WN2725
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16:00
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WN40
WN107
16:00
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16:00
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16:00
WN44
WN2103
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17:00
17:00
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WN44
WN107
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17:05
WN46
WN2725
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17:30
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WN46
WN107
17:30
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17:30
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WN46
WN1189
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17:45
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WN48
WN2103
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18:00
18:00
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WN50
WN1189
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18:45
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WN52
WN1359
19:00
19:00
19:00
19:00
19:00
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WN54
WN1359
20:30
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20:30
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 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
HOU
 
Via MCI
 
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
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Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN1037
WN2571
07:30
08:15
08:15
07:30
07:30
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WN1432
WN2572
09:25
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09:25
09:25
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WN4795
WN2029
12:00
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12:00
12:00
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WN1031
WN2787
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14:20
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SHOW RETURN SCHEDULE
CHECK PRICES FOR HOU - MDW

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

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