All airlines flying from Houston Hobby (HOU) to Chicago Midway (MDW).

FLIGHT SCHEDULE
Non-Direct Flights:
Sun 12:45 Houston Hobby (HOU) 16:50 Chicago Midway (MDW) Southwest Airlines WN 1546 1-stop Boeing 737-700 (Scimitar Winglets) 4:05 Operates only on 2026-05-24
Sat 12:25 Houston Hobby (HOU) 16:25 Chicago Midway (MDW) Southwest Airlines WN 1838 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Operates only on 2026-01-03
Sat 14:10 Houston Hobby (HOU) 19:30 Chicago Midway (MDW) Southwest Airlines WN 1962 1-stop Boeing 737 MAX 8 (7M8) 5:20 Effective 2026-06-06 through 2026-08-01
Mon,Thu,Fri 13:55 Houston Hobby (HOU) 17:45 Chicago Midway (MDW) Southwest Airlines WN 2015 1-stop Boeing 737-700 (Scimitar Winglets) 3:50 Effective 2026-03-05 through 2026-04-06
Mon,Thu,Fri 14:55 Houston Hobby (HOU) 18:50 Chicago Midway (MDW) Southwest Airlines WN 2029 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2026-06-04 through 2026-08-03
Mon,Thu,Fri 14:35 Houston Hobby (HOU) 19:25 Chicago Midway (MDW) Southwest Airlines WN 2151 1-stop Boeing 737 MAX 8 (7M8) 4:50 Effective 2026-04-09 through 2026-06-01
Sat 08:10 Houston Hobby (HOU) 12:10 Chicago Midway (MDW) Southwest Airlines WN 2359 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2026-04-11 through 2026-05-30
Sat 15:20 Houston Hobby (HOU) 19:20 Chicago Midway (MDW) Southwest Airlines WN 2607 1-stop Boeing 737-800 (73H) 4:00 Valid until 2026-01-03
Fri,Sun 17:25 Houston Hobby (HOU) 21:20 Chicago Midway (MDW) Southwest Airlines WN 2607 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2026-01-02 through 2026-01-04
Sun 08:05 Houston Hobby (HOU) 12:05 Chicago Midway (MDW) Southwest Airlines WN 2791 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2026-03-08 through 2026-04-05
Sat 07:50 Houston Hobby (HOU) 11:45 Chicago Midway (MDW) Southwest Airlines WN 2923 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Operates only on 2026-01-03
Sat 10:15 Houston Hobby (HOU) 14:20 Chicago Midway (MDW) Southwest Airlines WN 3056 1-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2026-03-07 through 2026-04-04
Sat 13:55 Houston Hobby (HOU) 17:45 Chicago Midway (MDW) Southwest Airlines WN 3180 1-stop Boeing 737-700 (Scimitar Winglets) 3:50 Effective 2026-03-07 through 2026-04-04
Mon,Thu,Fri 16:15 Houston Hobby (HOU) 20:20 Chicago Midway (MDW) Southwest Airlines WN 3305 1-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-03-05 through 2026-04-06
Sun 20:10 Houston Hobby (HOU) 00:15 Chicago Midway (MDW) Southwest Airlines WN 3342 1-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2026-04-12 through 2026-05-17 The flight arrives 1 day after departure.
Sun 20:10 Houston Hobby (HOU) 00:15 Chicago Midway (MDW) Southwest Airlines WN 3342 1-stop Boeing 737-700 (Scimitar Winglets) 4:05 Operates only on 2026-05-31 The flight arrives 1 day after departure.
Thu,Fri,Sun 12:45 Houston Hobby (HOU) 17:05 Chicago Midway (MDW) Southwest Airlines WN 4990 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2026-01-11 through 2026-01-16
Mon,Sun 12:45 Houston Hobby (HOU) 17:05 Chicago Midway (MDW) Southwest Airlines WN 4990 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 12:45 Houston Hobby (HOU) 17:05 Chicago Midway (MDW) Southwest Airlines WN 4990 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2026-02-01 through 2026-02-06
Mon,Sun 12:45 Houston Hobby (HOU) 17:05 Chicago Midway (MDW) Southwest Airlines WN 4990 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 12:45 Houston Hobby (HOU) 17:05 Chicago Midway (MDW) Southwest Airlines WN 4990 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2026-02-17 through 2026-02-23
Mon 12:45 Houston Hobby (HOU) 17:05 Chicago Midway (MDW) Southwest Airlines WN 4990 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Operates only on 2026-03-02
Sat 10:50 Houston Hobby (HOU) 16:50 Chicago Midway (MDW) Southwest Airlines WN 18 2-stop Boeing 737-800 (73H) 6:00 Effective 2026-04-11 through 2026-05-30
Wed,Thu 11:30 Houston Hobby (HOU) 17:00 Chicago Midway (MDW) Southwest Airlines WN 22 2-stop Boeing 737-700 (73W) 5:30 Valid until 2026-01-01
Sat 08:05 Houston Hobby (HOU) 13:55 Chicago Midway (MDW) Southwest Airlines WN 103 2-stop Boeing 737-700 (Scimitar Winglets) 5:50 Effective 2026-06-06 through 2026-08-01
Tue,Wed 08:10 Houston Hobby (HOU) 15:25 Chicago Midway (MDW) Southwest Airlines WN 284 2-stop Boeing 737-700 (Scimitar Winglets) 7:15 Effective 2026-06-09 through 2026-07-29
Sat 07:55 Houston Hobby (HOU) 14:25 Chicago Midway (MDW) Southwest Airlines WN 1907 2-stop Boeing 737-700 (Scimitar Winglets) 6:30 Operates only on 2026-01-03
Sat 08:10 Houston Hobby (HOU) 17:15 Chicago Midway (MDW) Southwest Airlines WN 1853 3-stop Boeing 737-700 (Scimitar Winglets) 9:05 Effective 2026-04-11 through 2026-05-30
Mon,Thu,Fri 10:10 Houston Hobby (HOU) 20:30 Chicago Midway (MDW) Southwest Airlines WN 4355 3-stop Boeing 737-700 (Scimitar Winglets) 10:20 Effective 2026-06-04 through 2026-08-03

1 2 3 4 5

A domestic route departing from the Houston Hobby airport (HOU) and arriving at Chicago Midway airport (MDW).
The flight distance is 937 miles, or 1509 km.
The timezone of both the departure and the arrival airports is UTC-6 . Current time at both airports is (loading...).
For direct flights, the flight time varies between 2:20 and 2:35.

Return (MDW-HOU) flights

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All airlines flying from Houston Hobby (HOU) to Chicago Midway (MDW).

FLIGHT SCHEDULE

Non-Direct Flights:

Southwest Airlines WN1546

12:45

Houston Hobby (HOU)

16:50

Chicago Midway (MDW)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:05, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1838

12:25

Houston Hobby (HOU)

16:25

Chicago Midway (MDW)

Operates only on 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1962

14:10

Houston Hobby (HOU)

19:30

Chicago Midway (MDW)

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:20, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN2015

13:55

Houston Hobby (HOU)

17:45

Chicago Midway (MDW)

Effective 2026-03-05 through 2026-04-06

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 3:50, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2029

14:55

Houston Hobby (HOU)

18:50

Chicago Midway (MDW)

Effective 2026-06-04 through 2026-08-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2151

14:35

Houston Hobby (HOU)

19:25

Chicago Midway (MDW)

Effective 2026-04-09 through 2026-06-01

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:50, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN2359

08:10

Houston Hobby (HOU)

12:10

Chicago Midway (MDW)

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2607

15:20

Houston Hobby (HOU)

19:20

Chicago Midway (MDW)

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:00, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN2607

17:25

Houston Hobby (HOU)

21:20

Chicago Midway (MDW)

Effective 2026-01-02 through 2026-01-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2791

08:05

Houston Hobby (HOU)

12:05

Chicago Midway (MDW)

Effective 2026-03-08 through 2026-04-05

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2923

07:50

Houston Hobby (HOU)

11:45

Chicago Midway (MDW)

Operates only on 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3056

10:15

Houston Hobby (HOU)

14:20

Chicago Midway (MDW)

Effective 2026-03-07 through 2026-04-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:05, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3180

13:55

Houston Hobby (HOU)

17:45

Chicago Midway (MDW)

Effective 2026-03-07 through 2026-04-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:50, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3305

16:15

Houston Hobby (HOU)

20:20

Chicago Midway (MDW)

Effective 2026-03-05 through 2026-04-06

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:05, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN3342

20:10

Houston Hobby (HOU)

00:15(+1)

Chicago Midway (MDW)

Effective 2026-04-12 through 2026-05-17

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:05, 1-stop
Boeing 737-700 (Scimitar Winglets)
The flight arrives 1 day after departure.

Non-Direct Flights:

Southwest Airlines WN3342

20:10

Houston Hobby (HOU)

00:15(+1)

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:05, 1-stop
Boeing 737-700 (Scimitar Winglets)
The flight arrives 1 day after departure.

Non-Direct Flights:

Southwest Airlines WN4990

12:45

Houston Hobby (HOU)

17:05

Chicago Midway (MDW)

Effective 2026-01-11 through 2026-01-16

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4990

12:45

Houston Hobby (HOU)

17:05

Chicago Midway (MDW)

Effective 2026-01-19 through 2026-01-25

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4990

12:45

Houston Hobby (HOU)

17:05

Chicago Midway (MDW)

Effective 2026-02-01 through 2026-02-06

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4990

12:45

Houston Hobby (HOU)

17:05

Chicago Midway (MDW)

Effective 2026-02-09 through 2026-02-15

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4990

12:45

Houston Hobby (HOU)

17:05

Chicago Midway (MDW)

Effective 2026-02-17 through 2026-02-23

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4990

12:45

Houston Hobby (HOU)

17:05

Chicago Midway (MDW)

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN18

10:50

Houston Hobby (HOU)

16:50

Chicago Midway (MDW)

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 6:00, 2-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN22

11:30

Houston Hobby (HOU)

17:00

Chicago Midway (MDW)

Valid until 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 5:30, 2-stop
Boeing 737-700 (73W)

Non-Direct Flights:

Southwest Airlines WN103

08:05

Houston Hobby (HOU)

13:55

Chicago Midway (MDW)

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:50, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN284

08:10

Houston Hobby (HOU)

15:25

Chicago Midway (MDW)

Effective 2026-06-09 through 2026-07-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 7:15, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1907

07:55

Houston Hobby (HOU)

14:25

Chicago Midway (MDW)

Operates only on 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 6:30, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1853

08:10

Houston Hobby (HOU)

17:15

Chicago Midway (MDW)

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 9:05, 3-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4355

10:10

Houston Hobby (HOU)

20:30

Chicago Midway (MDW)

Effective 2026-06-04 through 2026-08-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 10:20, 3-stop
Boeing 737-700 (Scimitar Winglets)

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A domestic route departing from the Houston Hobby airport (HOU) and arriving at Chicago Midway airport (MDW).
The flight distance is 937 miles, or 1509 km.
The timezone of both the departure and the arrival airports is UTC-6 . Current time at both airports is (loading...).
For direct flights, the flight time varies between 2:20 and 2:35.

Return (MDW-HOU) flights

Feedback - Disclaimer - Privacy