Southwest® flights from Chicago (Midway) to Houston (Hobby) from $79

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Low fares from Chicago (Midway) to Houston (Hobby)

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Chicago (Midway) (MDW)to

Houston (Hobby) (HOU)
Depart: 03/07/2026

One-way

Basic

From
$79
Seen: 17 hrs ago

Chicago (Midway) (MDW)to

Houston (Hobby) (HOU)
Depart: 03/10/2026

One-way

Basic

From
$79
Seen: 20 hrs ago

Chicago (Midway) (MDW)to

Houston (Hobby) (HOU)
Depart: 03/03/2026

One-way

Basic

From
$79
Seen: 9 hrs ago

Chicago (Midway) (MDW)to

Houston (Hobby) (HOU)
Depart: 04/04/2026

One-way

Basic

From
$80
Seen: 22 hrs ago

Chicago (Midway) (MDW)to

Houston (Hobby) (HOU)
Depart: 04/11/2026

One-way

Basic

From
$80
Seen: 22 hrs ago

Chicago (Midway) (MDW)to

Houston (Hobby) (HOU)
Depart: 03/04/2026

One-way

Basic

From
$90
Seen: 15 hrs ago
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Explore flights from Chicago (Midway) to Houston (Hobby)

Flight Details

Departing from:
Chicago Midway International Airport
Arriving at:
William P. Hobby Airport
Average flight time:
2 hours 35 minutes
Distance:
937 miles

Route Information

156 Weekly flights
  • 5 Nonstop flights per day Monday through Friday
  • 5 Nonstop flights on Saturday
  • 5 Nonstop flights on Sunday

† Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

Explore Houston (Hobby)

Take a flight from Chicago (Midway) to Houston (Hobby) with Southwest. Whether it’s your first time visiting or you’ve gone a hundred times, Houston always has something new to offer. Foodies enjoy the location for its diverse range of cuisine. The city has thousands of different restaurants that serve food from all over the world, although Tex-Mex is Houston’s claim to fame. For sports lovers, Houston is a dream come true. Catch a professional baseball, football, or basketball game while you’re in town and root for the home team. Is your head always in the clouds? Visit Space Center Houston to learn more about some of NASA’s most impressive rockets.

In addition to Space Center Houston, you will find plenty of other interesting museums to visit as well. The Museum of Natural Science is home to other space station models and also some pretty cool dinos—including four T-Rexes! For those individuals who like art, the Museum of Fine Arts covers more than 6,000 years of history with approximately 64,000 works from all over the world. Talk about impressive! Do you have little ones with you? Check out the Houston Children’s Museum, which offers fun exhibits the whole family can enjoy. After all that learning, you might like to get out and soak up some Houston sunshine (and we don’t blame you!) Take a stroll through one of Houston’s beautiful parks. Or rent a bike and hit a trail—it’s a win-win, either way!

Questions we hear the most

The average flight time from Chicago (Midway) to Houston (Hobby) is 2 hours 35 minutes.
There are 156 weekly flights from Chicago (Midway) to Houston (Hobby) on Southwest Airlines.
Yes, Southwest flies nonstop from Chicago (Midway) to Houston (Hobby) 5 times per day from Monday through Friday.
Yes, Southwest flies nonstop from Chicago (Midway) to Houston (Hobby) 5 times per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Chicago (Midway) to Houston (Hobby) with Southwest, check out our Low Fare Calendar.
You can rent a car at William P. Hobby Airport book yours with your flight.
Yes! Flights from Chicago (Midway) to Houston (Hobby)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Check the status of your upcoming Southwest flight.
Check out the Southwest Airlines® Help Center for answers about everything Southwest.

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