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!
Chicago (Midway), IL to Houston (Hobby), TX
departing on 8/15
one-way starting at*$89
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 17 travel days available.
|Departing from||Chicago Midway International Airport (MDW)|
|Arriving at||William P. Hobby Airport (HOU)|
|Average flight time||2 hours 33 minutes|
|4‡||Nonstop flights per day Monday through Friday|
|4‡||Nonstop flights on Saturday|
|5‡||Nonstop flights on Sunday|
Other popular flights from Chicago (Midway):View our interactive map
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 6/1/2023 and 6/30/2023. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 6/1/2023 and 6/30/2023.
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!
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.
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.
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.
When you arrive at William P. Hobby Airport, you'll be just seven miles from downtown Houston. What're you waiting for? Start exploring!
At Southwest, we know it takes more than great deals on Houston (Hobby) airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from Chicago (Midway) to Houston (Hobby) the best it can be. Learn more about the Southwest® travel experience before you book your flight from Chicago Midway International Airport to William P. Hobby Airport.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. When you search for your next flight to Houston (Hobby), know that you won’t be surprised at checkout. Low fares and no hidden fees. That's Transfarency®. And as always, two bags fly free®1. Want the latest news, information, and promotional offers from Southwest? Sign up to receive email from us. Book your flight today and know that you'll earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
3Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.
4Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our systems are updated. See full details here.
5Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
6Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
7Internet access for $8 per device from takeoff to landing. Price is subject to change. May not be available for the full duration of flight. In order to provide a top-notch Internet experience, we prohibit access to certain high-bandwidth applications and websites. We also prohibit access to certain obscene or offensive content.