SAR410 Cheap Flights from Houston (HOU) to Chicago (MDW)

View SAR410 flight on Mon, 25 May 2026Opens in a new window

Popular airlines from Houston William Hobby Airport (HOU) to Chicago Midway Airport (MDW)

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Cheap Flights from Houston to Chicago (HOU-MDW)

Prices were available within the past 7 days and start at SAR410 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from SAR 1,002
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from SAR 1,002

Frequently asked questions

Is it cheaper to buy a plane ticket from William P. Hobby Airport to Midway Intl. Airport (MDW) last minute?
When it comes to booking your flights, being prepared pays dividends. While you may be able to score a deal on a HOU to Midway Airport flight at the last minute, tickets usually don't get cheaper as the departure date nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to book a domestic flight is between 28 – 35 days ahead. For international trips it's three to four months.
What airports do you fly into for Chicago from Houston?
Midway Intl. Airport (MDW), O'Hare Intl. Airport (ORD) and Lewis University Airport (LOT) are your options when jetting off from Houston to Chicago. Roughly 14 kilometers southwest of the heart of Chicago, Midway Intl. Airport (MDW) is the city's main entry point. Consider things such as flight schedules and the distance to your hotel before deciding on an airport. Wrigley Field and Millennium Park are a couple of fantastic attractions to explore when you arrive.
Can I change the date of my flight from HOU to Midway Airport?
You can quickly and easily make changes to your William P. Hobby Airport (HOU) to Midway Airport trip through the Expedia Trips portal. Before you make any amendments, check the rules in your itinerary to find out what the airline will allow you to do and if change fees apply. Some airlines have a change fee per person, plus any difference in prices. However, if you booked in the last 24 hours, you may be able to cancel for free and organize new flights. You can also check out our Customer Service portal for more advice and to chat with our Virtual Agent.

Travel information

Origin airport
William P. Hobby
Destination airport
Midway Intl.
Distance
1500 km
Average flight time
2 hours 34 mins

Book with confidence

Houston to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Houston to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Houston to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is SAR410 now!

Houston to Chicago Flights