Trade the Capital of the Sunbelt for the Windy City—Southwest Airlines® flies from Houston (Hobby) to Chicago (Midway). The Big Heart of Texas will be easier to leave when you see the Midwest-nice fares at Southwest®. Book with confidence, knowing that you'll experience a straightforward process. Does your Houston excursion have flexible dates? Explore options on our Low Fare Calendar and discover the lowest fares on flights in your date range. Stack your savings and check out Southwest Vacations® for deals on hotels, rental cars, and more.
Check out flights from Houston (Hobby) to Chicago (Midway) and book your next trip!
Houston (Hobby), TX to Chicago (Midway), IL
departing on 10/29
one-way starting at*$79
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 19 travel days available.
|Departing from||William P. Hobby Airport (HOU)|
|Arriving at||Chicago Midway International Airport (MDW)|
|Average flight time||2 hours 25 minutes|
|5‡||Nonstop flights per day Monday through Friday|
|5‡||Nonstop flights on Saturday|
|4‡||Nonstop flights on Sunday|
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 10/1/2022 and 10/31/2022. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 10/1/2022 and 10/31/2022.
Everything may be bigger in Texas, but Texans will feel right at home when they trade Houston for Chicago—both are their respective states’ largest cities. Go big when you get to the City of the Big Shoulders and visit the tallest building in the Western hemisphere. The Willis Tower (locals still call it the Sears Tower) features the famous Skydeck Chicago Ledge, a glass outcropping 1,353 feet above the street below that’s sure to thrill (and make for some great selfies). Want to stay closer to terra firma? Grab a stuffed pizza from one of the big names in tourist cuisine, or chow down like a Chi-Town local and order yourself a thin-crust pie.
Depending on the time of year, Chicago has a range of indoor and outdoor activities, sights, and sounds to enjoy. Flora and fauna fans can visit the Lincoln Park Zoo, take a Metra train to the western suburbs to check out Brookfield Zoo, or take a different Metra line north of the city to the Chicago Botanic Garden. Chicago is lucky to experience each of the four seasons distinctly (sometimes all four in one day!), which means the foliage of the residential neighborhoods is a changing display year round. Neighborhoods throughout the city have thick canopies of trees over expansive parks and residential streets; be sure to take a stroll if you find yourself in Chi-Town in the fall to see the rainbow of foliage colors.
When you save on your flight from Houston (Hobby) to Chicago (Midway), you can spend your money on enjoying the destination rather than on upsells and fees.
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.
Chicago Midway International Airport is a quick 30-minute 'L' ride from downtown Chicago. Get going—adventure awaits.
At Southwest, we know it takes more than great deals on Chicago (Midway) 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 Houston (Hobby) to Chicago (Midway) the best it can be. Learn more about the Southwest® travel experience before you book your flight from William P. Hobby Airport to Chicago Midway International 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 Chicago (Midway), 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.
5Available only on WiFi-enabled aircraft. Limited-time offer. Where available.
6Internet access for $8 a day, per device. In order to provide the best experience, we block access to certain high-bandwidth applications, websites, and video conferencing services, including, but not limited to, Netflix, HBO Max, Zoom, and Microsoft Teams. In consideration of the public environment onboard, we also block potentially offensive online content.