Airlines with flights from Houston to Chicago

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

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.
  • 31 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 (winglets) Passenger/BBJ1
HOU
Direct
MDW
 
Flight
Mon
Feb 3
Tue
Feb 4
Wed
Feb 5
Thu
Feb 6
Fri
Feb 7
Sat
Feb 8
Sun
Feb 9
WN2332
06:55
06:55
06:55
05:55
05:55
08:00
06:55
WN2630
11:20
11:20
11:20
12:35
12:35
11:30
11:20
WN481
----
----
----
----
----
13:50
----
WN1260
14:35
14:35
14:35
17:00
17:00
----
14:35
WN1732
20:20
20:20
20:20
20:25
20:25
18:15
20:15
SHOW RETURN SCHEDULE
CHECK PRICES FOR HOU - MDW

The timetable & schedule information was updated at 2025-01-15

Via Dallas with Southwest Airlines

  • Total flight time: 4h 00m - 9h 00m.
  • Low-cost airline
  • Houston and Chicago are both Southwest Airlines focus cities.
  • 61 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 (winglets) Passenger/BBJ1
HOU
 
Via DAL
 
MDW
 
Flight
Mon
Feb 3
Tue
Feb 4
Wed
Feb 5
Thu
Feb 6
Fri
Feb 7
Sat
Feb 8
Sun
Feb 9
WN1636
WN1548
----
----
----
----
----
06:20
----
WN171
WN2364
06:25
06:25
06:25
----
----
----
06:25
WN1998
WN198
----
----
----
07:05
07:05
----
----
WN3542
WN6402
----
----
----
----
----
07:05
----
WN598
WN162
----
----
----
----
----
07:20
----
WN1998
WN736
07:25
07:25
07:25
----
----
----
07:25
WN993
WN1925
07:40
07:40
07:40
----
----
----
07:40
WN1010
WN1791
----
----
----
07:40
07:40
----
----
WN1010
WN1155
----
----
----
----
----
07:40
----
WN8
WN1365
08:00
08:00
08:00
----
----
----
08:00
WN1010
WN4877
08:20
08:20
08:20
----
----
----
08:20
WN1478
WN2364
----
----
----
----
----
08:30
----
WN10
WN2564
----
----
----
08:30
----
----
----
WN2470
WN1119
----
----
----
----
----
08:35
----
WN1181
WN1119
----
----
----
----
----
08:35
----
WN8
WN2514
----
----
----
----
----
08:35
----
WN2470
WN2434
----
----
----
----
----
08:35
----
WN198
WN6426
----
----
----
----
08:45
----
----
WN1181
WN2847
08:45
08:45
08:45
----
----
----
08:45
WN12
WN1365
09:00
09:00
09:00
----
----
----
09:00
WN12
WN2913
09:00
09:00
09:00
----
----
----
09:00
WN1158
WN262
09:20
09:20
09:20
----
----
----
09:20
WN1627
WN4877
----
----
----
----
----
09:20
----
WN6439
WN6426
----
----
----
----
09:30
----
----
WN4499
WN1354
----
----
----
----
----
09:40
----
WN1627
WN1471
----
----
----
09:45
09:45
----
----
WN16
WN2913
10:00
10:00
10:00
----
----
----
10:00
WN2239
WN2906
----
----
----
10:30
10:30
----
----
WN931
WN3079
10:30
10:30
10:30
----
----
----
10:30
WN18
WN2564
----
----
----
----
----
10:45
----
WN820
WN3293
----
----
----
11:05
11:05
----
----
WN1378
WN3293
11:25
11:25
11:25
12:30
12:30
----
11:25
WN22
WN948
----
----
----
11:30
11:30
----
----
WN22
WN2564
11:30
11:30
11:30
----
----
----
11:30
WN22
WN2973
----
----
----
11:30
11:30
----
----
WN2534
WN1496
----
----
----
12:05
12:05
----
----
WN26
WN2564
----
----
----
----
----
12:10
----
WN1560
WN4071
----
----
----
12:35
12:35
----
----
WN28
WN948
----
----
----
13:00
13:00
----
----
WN2376
WN3434
13:30
13:30
13:30
----
----
----
13:30
WN439
WN4928
----
----
----
13:35
13:35
----
----
WN3913
WN2804
----
----
----
13:35
13:35
----
----
WN4930
WN2039
----
----
----
13:45
13:45
----
----
WN2722
WN3360
----
----
----
----
----
13:45
----
WN2722
WN4703
14:20
14:20
14:20
15:35
15:35
----
----
WN2341
WN1647
----
----
----
14:25
14:25
----
----
WN34
WN40
----
----
----
14:30
14:30
----
----
WN34
WN2329
14:30
14:30
14:30
14:30
14:30
----
14:30
WN3726
WN3122
----
----
----
14:40
14:40
----
----
WN2633
WN1253
15:05
15:05
15:05
----
----
----
15:05
WN12
WN3474
----
----
----
----
----
15:25
----
WN3965
WN4703
----
----
----
15:45
15:45
----
----
WN40
WN381
16:00
16:00
16:00
----
----
----
----
WN40
WN298
----
----
----
16:00
16:00
----
----
WN3086
WN1647
----
----
----
16:35
16:35
----
----
WN44
WN381
17:00
17:00
17:00
----
----
----
----
WN46
WN381
----
----
----
17:30
17:30
----
----
WN2633
WN3012
----
----
----
17:50
17:50
----
----
WN1647
WN2965
18:25
18:25
18:25
----
----
----
----
WN1525
WN1647
----
----
----
18:25
18:25
----
----
WN52
WN381
----
----
----
19:00
19:00
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR HOU - MDW

The timetable & schedule information was updated at 2025-01-15

Via Nashville with Southwest Airlines

  • Total flight time: 4h 05m - 8h 30m.
  • 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 (winglets) Passenger/BBJ1
HOU
 
Via BNA
 
MDW
 
Flight
Mon
Feb 3
Tue
Feb 4
Wed
Feb 5
Thu
Feb 6
Fri
Feb 7
Sat
Feb 8
Sun
Feb 9
WN1636
WN1548
----
----
----
----
----
06:20
----
WN171
WN2364
06:25
06:25
06:25
----
----
----
06:25
WN1998
WN198
----
----
----
07:05
07:05
----
----
WN3542
WN6402
----
----
----
----
----
07:05
----
WN598
WN162
----
----
----
----
----
07:20
----
WN1998
WN736
07:25
07:25
07:25
----
----
----
07:25
WN993
WN1925
07:40
07:40
07:40
----
----
----
07:40
WN1010
WN1791
----
----
----
07:40
07:40
----
----
WN1010
WN1155
----
----
----
----
----
07:40
----
WN8
WN1365
08:00
08:00
08:00
----
----
----
08:00
WN1010
WN4877
08:20
08:20
08:20
----
----
----
08:20
WN1478
WN2364
----
----
----
----
----
08:30
----
WN10
WN2564
----
----
----
08:30
----
----
----
WN2470
WN1119
----
----
----
----
----
08:35
----
WN1181
WN1119
----
----
----
----
----
08:35
----
WN8
WN2514
----
----
----
----
----
08:35
----
WN2470
WN2434
----
----
----
----
----
08:35
----
WN198
WN6426
----
----
----
----
08:45
----
----
WN1181
WN2847
08:45
08:45
08:45
----
----
----
08:45
WN12
WN1365
09:00
09:00
09:00
----
----
----
09:00
WN12
WN2913
09:00
09:00
09:00
----
----
----
09:00
WN1158
WN262
09:20
09:20
09:20
----
----
----
09:20
WN1627
WN4877
----
----
----
----
----
09:20
----
WN6439
WN6426
----
----
----
----
09:30
----
----
WN4499
WN1354
----
----
----
----
----
09:40
----
WN1627
WN1471
----
----
----
09:45
09:45
----
----
WN16
WN2913
10:00
10:00
10:00
----
----
----
10:00
WN2239
WN2906
----
----
----
10:30
10:30
----
----
WN931
WN3079
10:30
10:30
10:30
----
----
----
10:30
WN18
WN2564
----
----
----
----
----
10:45
----
WN820
WN3293
----
----
----
11:05
11:05
----
----
WN1378
WN3293
11:25
11:25
11:25
12:30
12:30
----
11:25
WN22
WN948
----
----
----
11:30
11:30
----
----
WN22
WN2564
11:30
11:30
11:30
----
----
----
11:30
WN22
WN2973
----
----
----
11:30
11:30
----
----
WN2534
WN1496
----
----
----
12:05
12:05
----
----
WN26
WN2564
----
----
----
----
----
12:10
----
WN1560
WN4071
----
----
----
12:35
12:35
----
----
WN28
WN948
----
----
----
13:00
13:00
----
----
WN2376
WN3434
13:30
13:30
13:30
----
----
----
13:30
WN439
WN4928
----
----
----
13:35
13:35
----
----
WN3913
WN2804
----
----
----
13:35
13:35
----
----
WN4930
WN2039
----
----
----
13:45
13:45
----
----
WN2722
WN3360
----
----
----
----
----
13:45
----
WN2722
WN4703
14:20
14:20
14:20
15:35
15:35
----
----
WN2341
WN1647
----
----
----
14:25
14:25
----
----
WN34
WN40
----
----
----
14:30
14:30
----
----
WN34
WN2329
14:30
14:30
14:30
14:30
14:30
----
14:30
WN3726
WN3122
----
----
----
14:40
14:40
----
----
WN2633
WN1253
15:05
15:05
15:05
----
----
----
15:05
WN12
WN3474
----
----
----
----
----
15:25
----
WN3965
WN4703
----
----
----
15:45
15:45
----
----
WN40
WN381
16:00
16:00
16:00
----
----
----
----
WN40
WN298
----
----
----
16:00
16:00
----
----
WN3086
WN1647
----
----
----
16:35
16:35
----
----
WN44
WN381
17:00
17:00
17:00
----
----
----
----
WN46
WN381
----
----
----
17:30
17:30
----
----
WN2633
WN3012
----
----
----
17:50
17:50
----
----
WN1647
WN2965
18:25
18:25
18:25
----
----
----
----
WN1525
WN1647
----
----
----
18:25
18:25
----
----
WN52
WN381
----
----
----
19:00
19:00
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR HOU - MDW

The timetable & schedule information was updated at 2025-01-15

Via Saint Louis with Southwest Airlines

  • Total flight time: 3h 45m - 8h 15m.
  • Low-cost airline
  • Houston and Chicago are both Southwest Airlines focus cities.
  • 20 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 (winglets) Passenger/BBJ1
HOU
 
Via STL
 
MDW
 
Flight
Mon
Feb 3
Tue
Feb 4
Wed
Feb 5
Thu
Feb 6
Fri
Feb 7
Sat
Feb 8
Sun
Feb 9
WN1636
WN1548
----
----
----
----
----
06:20
----
WN171
WN2364
06:25
06:25
06:25
----
----
----
06:25
WN1998
WN198
----
----
----
07:05
07:05
----
----
WN3542
WN6402
----
----
----
----
----
07:05
----
WN598
WN162
----
----
----
----
----
07:20
----
WN1998
WN736
07:25
07:25
07:25
----
----
----
07:25
WN993
WN1925
07:40
07:40
07:40
----
----
----
07:40
WN1010
WN1791
----
----
----
07:40
07:40
----
----
WN1010
WN1155
----
----
----
----
----
07:40
----
WN8
WN1365
08:00
08:00
08:00
----
----
----
08:00
WN1010
WN4877
08:20
08:20
08:20
----
----
----
08:20
WN1478
WN2364
----
----
----
----
----
08:30
----
WN10
WN2564
----
----
----
08:30
----
----
----
WN2470
WN1119
----
----
----
----
----
08:35
----
WN1181
WN1119
----
----
----
----
----
08:35
----
WN8
WN2514
----
----
----
----
----
08:35
----
WN2470
WN2434
----
----
----
----
----
08:35
----
WN198
WN6426
----
----
----
----
08:45
----
----
WN1181
WN2847
08:45
08:45
08:45
----
----
----
08:45
WN12
WN1365
09:00
09:00
09:00
----
----
----
09:00
WN12
WN2913
09:00
09:00
09:00
----
----
----
09:00
WN1158
WN262
09:20
09:20
09:20
----
----
----
09:20
WN1627
WN4877
----
----
----
----
----
09:20
----
WN6439
WN6426
----
----
----
----
09:30
----
----
WN4499
WN1354
----
----
----
----
----
09:40
----
WN1627
WN1471
----
----
----
09:45
09:45
----
----
WN16
WN2913
10:00
10:00
10:00
----
----
----
10:00
WN2239
WN2906
----
----
----
10:30
10:30
----
----
WN931
WN3079
10:30
10:30
10:30
----
----
----
10:30
WN18
WN2564
----
----
----
----
----
10:45
----
WN820
WN3293
----
----
----
11:05
11:05
----
----
WN1378
WN3293
11:25
11:25
11:25
12:30
12:30
----
11:25
WN22
WN948
----
----
----
11:30
11:30
----
----
WN22
WN2564
11:30
11:30
11:30
----
----
----
11:30
WN22
WN2973
----
----
----
11:30
11:30
----
----
WN2534
WN1496
----
----
----
12:05
12:05
----
----
WN26
WN2564
----
----
----
----
----
12:10
----
WN1560
WN4071
----
----
----
12:35
12:35
----
----
WN28
WN948
----
----
----
13:00
13:00
----
----
WN2376
WN3434
13:30
13:30
13:30
----
----
----
13:30
WN439
WN4928
----
----
----
13:35
13:35
----
----
WN3913
WN2804
----
----
----
13:35
13:35
----
----
WN4930
WN2039
----
----
----
13:45
13:45
----
----
WN2722
WN3360
----
----
----
----
----
13:45
----
WN2722
WN4703
14:20
14:20
14:20
15:35
15:35
----
----
WN2341
WN1647
----
----
----
14:25
14:25
----
----
WN34
WN40
----
----
----
14:30
14:30
----
----
WN34
WN2329
14:30
14:30
14:30
14:30
14:30
----
14:30
WN3726
WN3122
----
----
----
14:40
14:40
----
----
WN2633
WN1253
15:05
15:05
15:05
----
----
----
15:05
WN12
WN3474
----
----
----
----
----
15:25
----
WN3965
WN4703
----
----
----
15:45
15:45
----
----
WN40
WN381
16:00
16:00
16:00
----
----
----
----
WN40
WN298
----
----
----
16:00
16:00
----
----
WN3086
WN1647
----
----
----
16:35
16:35
----
----
WN44
WN381
17:00
17:00
17:00
----
----
----
----
WN46
WN381
----
----
----
17:30
17:30
----
----
WN2633
WN3012
----
----
----
17:50
17:50
----
----
WN1647
WN2965
18:25
18:25
18:25
----
----
----
----
WN1525
WN1647
----
----
----
18:25
18:25
----
----
WN52
WN381
----
----
----
19:00
19:00
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR HOU - MDW

The timetable & schedule information was updated at 2025-01-15

Via Atlanta with Southwest Airlines

  • Total flight time: 4h 30m - 8h 25m.
  • Low-cost airline
  • Houston and Chicago are both Southwest Airlines focus cities.
  • 15 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 (winglets) Passenger/BBJ1
HOU
 
Via ATL
 
MDW
 
Flight
Mon
Feb 3
Tue
Feb 4
Wed
Feb 5
Thu
Feb 6
Fri
Feb 7
Sat
Feb 8
Sun
Feb 9
WN1636
WN1548
----
----
----
----
----
06:20
----
WN171
WN2364
06:25
06:25
06:25
----
----
----
06:25
WN1998
WN198
----
----
----
07:05
07:05
----
----
WN3542
WN6402
----
----
----
----
----
07:05
----
WN598
WN162
----
----
----
----
----
07:20
----
WN1998
WN736
07:25
07:25
07:25
----
----
----
07:25
WN993
WN1925
07:40
07:40
07:40
----
----
----
07:40
WN1010
WN1791
----
----
----
07:40
07:40
----
----
WN1010
WN1155
----
----
----
----
----
07:40
----
WN8
WN1365
08:00
08:00
08:00
----
----
----
08:00
WN1010
WN4877
08:20
08:20
08:20
----
----
----
08:20
WN1478
WN2364
----
----
----
----
----
08:30
----
WN10
WN2564
----
----
----
08:30
----
----
----
WN2470
WN1119
----
----
----
----
----
08:35
----
WN1181
WN1119
----
----
----
----
----
08:35
----
WN8
WN2514
----
----
----
----
----
08:35
----
WN2470
WN2434
----
----
----
----
----
08:35
----
WN198
WN6426
----
----
----
----
08:45
----
----
WN1181
WN2847
08:45
08:45
08:45
----
----
----
08:45
WN12
WN1365
09:00
09:00
09:00
----
----
----
09:00
WN12
WN2913
09:00
09:00
09:00
----
----
----
09:00
WN1158
WN262
09:20
09:20
09:20
----
----
----
09:20
WN1627
WN4877
----
----
----
----
----
09:20
----
WN6439
WN6426
----
----
----
----
09:30
----
----
WN4499
WN1354
----
----
----
----
----
09:40
----
WN1627
WN1471
----
----
----
09:45
09:45
----
----
WN16
WN2913
10:00
10:00
10:00
----
----
----
10:00
WN2239
WN2906
----
----
----
10:30
10:30
----
----
WN931
WN3079
10:30
10:30
10:30
----
----
----
10:30
WN18
WN2564
----
----
----
----
----
10:45
----
WN820
WN3293
----
----
----
11:05
11:05
----
----
WN1378
WN3293
11:25
11:25
11:25
12:30
12:30
----
11:25
WN22
WN948
----
----
----
11:30
11:30
----
----
WN22
WN2564
11:30
11:30
11:30
----
----
----
11:30
WN22
WN2973
----
----
----
11:30
11:30
----
----
WN2534
WN1496
----
----
----
12:05
12:05
----
----
WN26
WN2564
----
----
----
----
----
12:10
----
WN1560
WN4071
----
----
----
12:35
12:35
----
----
WN28
WN948
----
----
----
13:00
13:00
----
----
WN2376
WN3434
13:30
13:30
13:30
----
----
----
13:30
WN439
WN4928
----
----
----
13:35
13:35
----
----
WN3913
WN2804
----
----
----
13:35
13:35
----
----
WN4930
WN2039
----
----
----
13:45
13:45
----
----
WN2722
WN3360
----
----
----
----
----
13:45
----
WN2722
WN4703
14:20
14:20
14:20
15:35
15:35
----
----
WN2341
WN1647
----
----
----
14:25
14:25
----
----
WN34
WN40
----
----
----
14:30
14:30
----
----
WN34
WN2329
14:30
14:30
14:30
14:30
14:30
----
14:30
WN3726
WN3122
----
----
----
14:40
14:40
----
----
WN2633
WN1253
15:05
15:05
15:05
----
----
----
15:05
WN12
WN3474
----
----
----
----
----
15:25
----
WN3965
WN4703
----
----
----
15:45
15:45
----
----
WN40
WN381
16:00
16:00
16:00
----
----
----
----
WN40
WN298
----
----
----
16:00
16:00
----
----
WN3086
WN1647
----
----
----
16:35
16:35
----
----
WN44
WN381
17:00
17:00
17:00
----
----
----
----
WN46
WN381
----
----
----
17:30
17:30
----
----
WN2633
WN3012
----
----
----
17:50
17:50
----
----
WN1647
WN2965
18:25
18:25
18:25
----
----
----
----
WN1525
WN1647
----
----
----
18:25
18:25
----
----
WN52
WN381
----
----
----
19:00
19:00
----
----
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The timetable & schedule information was updated at 2025-01-15

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