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!
Best Airline in the U.S. and North America & Best Economy Class and Low Cost Airline in North America.
Houston (Hobby), TX to Chicago (Midway), IL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 22 travel days available.
During the ongoing COVID-19 pandemic, the availability, health and safety procedures, operations, and schedules for local attractions are changing constantly. Please contact attractions directly for hours of operation, potential temperature screenings, and other possible health and safety procedures and restrictions. Visit our COVID-19 Travel Information page for information about potential restrictions on air travel.
| Departing from | William P. Hobby Airport (HOU) |
|---|---|
| Arriving at | Chicago Midway International Airport (MDW) |
| Average flight time | 2 hours 21 minutes |
| Distance | 937 miles |
| 101† | Weekly flights |
|---|---|
| 4‡ | Nonstop flights per day Monday through Friday |
| 4‡ | Nonstop flights on Saturday |
| 5‡ | Nonstop flights on Sunday |
Other popular flights from Houston (Hobby):
View our interactive map†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 10/1/2021 and 10/31/2021. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 10/1/2021 and 10/31/2021.
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.
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. Looking for tours, activities, and more hidden gems to add to your Chicago (Midway) adventure? Explore getaways with Southwest®. 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.
The average flight time from Houston (Hobby) to Chicago (Midway) is 2 hours 21 minutes.
There are 101 weekly flights from Houston (Hobby) to Chicago (Midway) on Southwest Airlines.
Yes, Southwest flies nonstop from Houston (Hobby) to Chicago (Midway) 4 times per day from Monday through Friday.
Yes, Southwest flies nonstop from Houston (Hobby) to Chicago (Midway) 4 times per day on Saturdays and 5 times per day on Sundays.
To find the lowest fares by day and time to fly Houston (Hobby) to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
You can rent a car at Chicago Midway International Airport—book yours with your flight.
Yes! Flights from Houston (Hobby) to Chicago (Midway)—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® FAQs for answers about everything Southwest.
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