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 cheapest 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!
Average flight time: 2 hours 25 minutes
Departing from: William P. Hobby Airport / Houston Hobby (HOU)
Arriving at: Chicago Midway International Airport (MDW)
Nonstop flightsper day
Other popular flights from HoustonView our interactive map
*Based on DOT published scheduled average Monday-Friday departures between 6/29/2020 and 1/4/2021, as of 6/29/2020.
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.
Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.
We know that a memorable trip is made of more than scoring a cheap flight from Houston (Hobby) to Chicago (Midway). That's why Southwest offers travelers other services and perks, from booking to boarding, that combine to make your experience as smooth as possible. Find out more about the Southwest Experience and book your Houston (Hobby) to Chicago (Midway) flight.
Flying with Southwest is simple, fun, and straightforward. When you select a flight from Houston (Hobby) to Chicago (Midway), there will be no hidden fees, low fares, and, as always, bags fly free. That's Transfarency®. Stay up to date on our deals by enrolling in the Click 'N Save® emails. Looking for tours, activities, and more hidden gems? Check out 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.