Flights from Chicago (MDW) to Houston (HOU)

Trade in your gym shoes for a pair of cowboy boots! Fly from Chicago Midway International Airport to William P. Hobby Airport/Houston (Hobby) with Southwest Airlines®. Southwest® has great deals on flights from Chicago (Midway) to Houston (Hobby) all year round. Enjoy low fares with Southwest and book with confidence. Does your trip have flexible dates? Search for flights with our Low Fare Calendar and discover the lowest fares we’ve got. Looking for more deals? Be sure to explore Southwest Vacations® for package deals on flights, hotels, rental cars, and more.

Find Chicago (Midway) to Houston (Hobby) flights and book your trip today!

TripAdvisor has rated us #1.

Best Airline in the U.S. and North America & Best Economy and Low Cost Airline in North America.

Low fare alert

Chicago (Midway), IL to Houston (Hobby), TX

departing on 10/24

one-way starting at*

Book now

*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 19 travel days available.

Check out Chicago (Midway) to Houston (Hobby) flights and book yours now!

Middle seats open through November 30

Full exchange of fresh, outdoor air every 2-3 minutes while inflight

Face coverings required

Flight details

Average flight time: 2 hours 46 minutes

Departing from: Chicago Midway International Airport (MDW)

Arriving at: William P. Hobby Airport / Houston Hobby (HOU)


Route information


Nonstop flightsper day


Daily flights


Weekly flights


Flightsbefore noon




Flightsafter 6pm

View our interactive map

Based on DOT published scheduled average flights Monday-Friday between 8/20/2020 and 4/11/2021, as of 8/20/2020.

Explore Houston

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!

If you’re an animal lover, you can meet marine animals at the Downtown Aquarium or say hello to tigers at the Houston Zoo. Or even more astonishing, go to Waugh Bridge to see a colony of 250,000 Mexican free-tailed bats emerge at dusk and feast on insects! After you see the animals, go out for a delicious dinner. While Houston is famous for Tex-Mex and craft beer, you still might want to check out Houston’s Chinatown for classic and contemporary Chinese dishes that are packed with flavor. With so many great dining options, it will be hard to choose!

Travel tips


Infancy policy

One child over 14 days and under two (2) years of age, not occupying a seat, may be carried free of charge when traveling with an adult (12 years of age or older). Learn more.


Pet policy

Customers flying with a pet are subject to a pet fare. To learn more about traveling with your furry friend, explore the Southwest® pet policy.


Unaccompanied minor

Minors under the age of 18 are not permitted to fly unaccompanied on international flights or any itinerary that includes an international flight. Learn more.


Bags fly free®1

Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.


The Southwest travel experience

At Southwest, we know that a memorable trip from Chicago (Midway) to Houston (Hobby) is built on more than low fares. That’s why we offer services and perks, from booking to boarding, to make your flight from Chicago Midway International Airport to William P. Hobby Airport/Houston (Hobby) smoother than ever. Learn more about the Southwest® Experience before you book your flight to Houston.

Pick your destination and book your flight. Feel confident knowing that flying with Southwest is simple and fun. When you book with Southwest, you can count on low fares and no hidden fees. And, as always, bags fly free. That’s our Transfarency® promise. Enroll in our Click 'N Save® emails to learn more about our latest flight deals. If you’re looking for tours, activities, and more hidden gems, explore Southwest Airlines® Experiences and earn Rapid Rewards® points when you fly.

1First and second checked bags. Weight and size limits apply.

2Fare difference may apply.