Which airport are you flying from?

Direct flights from Houston to Chicago

Airlines Schedules

HOU - MDW route map All flights from HOU to MDW non-stop. There are direct flights from William P. Hobby Airport (HOU), Texas, USA to Chicago Midway International (MDW), Illinois, USA with Southwest Airlines. 37 weekly departures are currently scheduled on this route. Departure times range from 05:00 to 22:40 depending on the schedule period. The flight distance is 943 miles (1517 km). Flight time ranges from 2 hours and 20 minutes to 2 hours and 35 minutes.

HOU
William P. Hobby Airport
USAHouston , USA
MDW
Chicago Midway
USAChicago , USA
HOU
William P. Hobby Airport
USAHouston , USA
Chicago Midway
USAChicago , USA
MDW
Flight time 2h 20min to 2h 35min
Updated Aug 31, 2026
CHANGE DIRECTION

Airlines with non-stop routes:

Southwest Airlines Low-cost carrier

Departure times vary between 05:00 and 22:40
S
M
T
W
T
F
S
Sun
Mon
Tue
Wed
Thu
Fri
Sat
37 flights/week
37 flights/week
Weekday-labels: HAS FLIGHTS UPCOMING NO FLIGHTS
View all flight dates
Flight schedule from Houston to Chicago with Southwest Airlines

This is a weekly direct flight schedule for Southwest Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.

 
Flight
Mon
Sep 28
Tue
Sep 29
Wed
Sep 30
Thu
Oct 1
Fri
Oct 2
Sat
Oct 3
Sun
Oct 4
WN1156
05:00
----
----
----
----
----
----
WN1444
----
----
----
05:00
05:00
----
----
WN149
----
06:50
07:00
----
----
----
----
WN265
07:20
16:45
16:45
----
----
----
----
WN4638
----
----
----
----
----
08:25
07:50
WN2085
----
----
----
08:55
08:55
----
----
WN256
----
09:40
09:40
----
----
----
----
WN2828
----
----
----
----
----
----
11:50
WN234
----
----
----
12:55
12:55
----
----
WN1179
----
----
----
----
----
13:30
----
WN1964
14:20
----
----
----
----
----
----
WN1966
17:45
14:45
14:45
----
----
----
----
WN2087
----
----
----
15:20
15:20
----
----
WN2103
----
----
----
----
----
----
15:55
WN152
16:10
----
----
----
----
----
----
WN1339
----
----
----
----
----
17:30
----
WN43
----
----
----
18:50
18:50
----
----
WN2088
----
----
----
----
----
----
19:05
WN4789
----
----
----
19:50
19:50
19:50
22:30
WN2771
19:55
----
----
----
----
----
----
WN2278
----
20:50
20:50
----
----
----
----

The timetable & schedule information was updated at 2026-08-31

RETURN SCHEDULE
CHECK PRICES
SPONSORED AD

Houston to Chicago scheduled departures

Select a date to see every published non-stop departure between HOU and MDW.

Saturday
Sat
Sep 26
4 flights(4)
Sunday
Sun
Sep 27
6 flights(6)
Monday
Mon
Sep 28
6 flights(6)
Tuesday
Tue
Sep 29
5 flights(5)
Wednesday
Wed
Sep 30
5 flights(5)
Thursday
Thu
Oct 01
6 flights(6)
Friday
Fri
Oct 02
6 flights(6)
Time
Airline
Flight
07:00
Southwest Airlines Southwest Airlines
WN149
10:30
Southwest Airlines Southwest Airlines
WN398
15:15
Southwest Airlines Southwest Airlines
WN1966
19:40
Southwest Airlines Southwest Airlines
WN2771
05:40
Southwest Airlines Southwest Airlines
WN149
08:20
Southwest Airlines Southwest Airlines
WN256
11:55
Southwest Airlines Southwest Airlines
WN1988
14:50
Southwest Airlines Southwest Airlines
WN111
18:15
Southwest Airlines Southwest Airlines
WN265
21:50
Southwest Airlines Southwest Airlines
WN2278
05:00
Southwest Airlines Southwest Airlines
WN1156
07:20
Southwest Airlines Southwest Airlines
WN265
14:20
Southwest Airlines Southwest Airlines
WN1964
16:10
Southwest Airlines Southwest Airlines
WN152
17:45
Southwest Airlines Southwest Airlines
WN1966
19:55
Southwest Airlines Southwest Airlines
WN2771
06:50
Southwest Airlines Southwest Airlines
WN149
09:40
Southwest Airlines Southwest Airlines
WN256
14:45
Southwest Airlines Southwest Airlines
WN1966
16:45
Southwest Airlines Southwest Airlines
WN265
20:50
Southwest Airlines Southwest Airlines
WN2278
07:00
Southwest Airlines Southwest Airlines
WN149
09:40
Southwest Airlines Southwest Airlines
WN256
14:45
Southwest Airlines Southwest Airlines
WN1966
16:45
Southwest Airlines Southwest Airlines
WN265
20:50
Southwest Airlines Southwest Airlines
WN2278
05:00
Southwest Airlines Southwest Airlines
WN1444
08:55
Southwest Airlines Southwest Airlines
WN2085
12:55
Southwest Airlines Southwest Airlines
WN234
15:20
Southwest Airlines Southwest Airlines
WN2087
18:50
Southwest Airlines Southwest Airlines
WN43
19:50
Southwest Airlines Southwest Airlines
WN4789
05:00
Southwest Airlines Southwest Airlines
WN1444
08:55
Southwest Airlines Southwest Airlines
WN2085
12:55
Southwest Airlines Southwest Airlines
WN234
15:20
Southwest Airlines Southwest Airlines
WN2087
18:50
Southwest Airlines Southwest Airlines
WN43
19:50
Southwest Airlines Southwest Airlines
WN4789
SPONSORED AD
HOU-MDW flight route
Route map from Houston, HOU to Chicago, MDW. The distance is 943 miles or 1517 km.
Houston - Chicago direct flight map
SPONSORED AD
SPONSORED AD

HOU - MDW route facts

  • Distance
    943 miles (1517 km)
  • Flight time
    2 hours and 20 minutes to 2 hours and 35 minutes
  • Airline
    Southwest Southwest
  • Airline alliances
    Low-cost carrier
  • Cabins
    Economy
  • Aircraft
    Boeing 737-700 Passenger (Scimitar Winglets) , Boeing 737MAX 8 Passenger and Boeing 737-800 (winglets) Passenger/BBJ2

Route FAQ

Southwest Airlines operates non-stop flights from HOU to MDW with 37 weekly departures.

Scheduled flight time from HOU to MDW ranges from 2 hours and 20 minutes to 2 hours and 35 minutes. The route covers 943 miles (1517 km).

37 weekly departures are currently scheduled on this route, with published departure times ranging from 05:00 to 22:40 depending on the schedule period.

Economy are currently scheduled on non-stop flights for this route.
SPONSORED AD
SPONSORED AD