Southwest Airlines
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United States
William P. Hobby Airport
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United States
Midway International Airport
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Scan through all non-stop flights from Houston to Chicago. The full flight schedule below gives an overview of all non-stop flights from HOU to MDW, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Known for its continental climate, Chicago features hot, humid summers with temperatures above 30°C (86°F) and cold, snowy winters that often drop below 0°C (32°F). This striking seasonal contrast offers travelers a variety of activities, from summer hiking to winter sports, ensuring year-round appeal.
The best time to visit Chicago is from March to November, covering spring, summer, and fall. While summer can be hot, it also sees slightly more rainfall than other seasons.
Currently, there is only one airline operating non-stop flights from Houston HOU to Chicago MDW, which is Southwest Airlines. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.
Click an airline below to view their HOU MDW flight schedule.
Flights from HOU to MDW are operated 34 times a week, with an average of 5 flights per day. Departure times vary between 05:00 - 22:35. The earliest flight departs at 05:00, the last flight departs at 22:35. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.
On this non-stop route, you can fly in Economy only.
The fastest direct flight from Houston to Chicago takes 2 hours and 25 minutes. The flight distance between Houston and Chicago is 937 miles (or 1,508 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There are 34 flights per week flying from Houston to Chicago (as of April 2026).
2 hours and 25 minutes is the average flight time from Houston to Chicago.
The distance from Houston to Chicago is 937 miles (1,508 kilometers).
Southwest Airlines is the only airline flying nonstop from Houston to Chicago.
There are no alliances flying direct from Houston to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Houston to Chicago:
The earliest flight departs at 05:00 from Houston and arrives at 07:20 at Chicago.
The latest flight departs at 22:35 from Houston and arrives at 00:55 at Chicago.
937 miles (1,508 km) · 2h 25m
05:00
07:20
Southwest Airlines
WN 2968
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
05:00
07:25
Southwest Airlines
WN 3907
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
05:05
07:25
Southwest Airlines
WN 3490
Southwest Airlines
Boeing 757
Y
W
J
F
05:10
07:35
Southwest Airlines
WN 3755
Southwest Airlines
Boeing 757
Y
W
J
F
05:15
07:35
Southwest Airlines
WN 473
Southwest Airlines
Boeing 757
Y
W
J
F
07:00
09:25
Southwest Airlines
WN 2963
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:10
09:35
Southwest Airlines
WN 4520
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
08:00
10:25
Southwest Airlines
WN 2963
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
08:10
10:35
Southwest Airlines
WN 2649
Southwest Airlines
Boeing 757
Y
W
J
F
08:10
10:35
Southwest Airlines
WN 2963
Southwest Airlines
Boeing 757
Y
W
J
F
08:15
10:40
Southwest Airlines
WN 2649
Southwest Airlines
Boeing 757
Y
W
J
F
09:15
11:40
Southwest Airlines
WN 2002
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
09:35
12:00
Southwest Airlines
WN 2649
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
12:20
14:40
Southwest Airlines
WN 4642
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
12:25
14:45
Southwest Airlines
WN 4642
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
12:40
15:05
Southwest Airlines
WN 2002
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
12:55
15:25
Southwest Airlines
WN 2002
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
14:25
16:50
Southwest Airlines
WN 2373
Southwest Airlines
Boeing 757
Y
W
J
F
14:50
17:10
Southwest Airlines
WN 3433
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
15:00
17:20
Southwest Airlines
WN 3433
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
15:10
17:30
Southwest Airlines
WN 3433
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
15:20
17:45
Southwest Airlines
WN 123
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
15:25
17:50
Southwest Airlines
WN 3395
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
15:25
17:50
Southwest Airlines
WN 3395
Southwest Airlines
Boeing 757
Y
W
J
F
18:10
20:35
Southwest Airlines
WN 123
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
18:25
20:45
Southwest Airlines
WN 359
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
18:50
21:15
Southwest Airlines
WN 222
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
19:00
21:20
Southwest Airlines
WN 4621
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
19:10
21:30
Southwest Airlines
WN 1779
Southwest Airlines
Boeing 757
Y
W
J
F
19:30
21:55
Southwest Airlines
WN 2373
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
20:20
22:45
Southwest Airlines
WN 2373
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
20:25
22:50
Southwest Airlines
WN 1575
Southwest Airlines
Boeing 757
Y
W
J
F
20:40
23:05
Southwest Airlines
WN 2963
Southwest Airlines
Boeing 757
Y
W
J
F
21:15
23:40
Southwest Airlines
WN 1575
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
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