$59 Cheap Flights from Houston (HOU) to Chicago (MDW)

View $59 flight on Fri, Feb 20, 2026Opens in a new window

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

Cheap Flights from Houston to Chicago (HOU-MDW)

Prices were available within the past 7 days and start at $59 for one-way flights and $117 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Fri, Feb 20 - Mon, Feb 23
HOU
Houston
MDW
Chicago
$117 Roundtrip, just found
$117
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Feb 20 from Houston to Chicago, returning Mon, Feb 23, priced at $117 just found

Find the cheapest month to fly from Houston (HOU) to Chicago (MDW)

October is typically the cheapest month to fly

From $83 - $316 per traveler.

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 $110
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $110
Flights from Houston (HOU) to Chicago (MDW)
Origin airport
William P. Hobby
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$117
Distance
937 mi
Average flight time
2 hours 23 mins

Houston to Chicago Flights

The cheapest times to fly from Houston to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Houston to Chicago are during the month of February. You can find some of the cheapest flights from Houston to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Houston to Chicago

Sunday is one of the best days to book for cheap flights from Houston to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Houston to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Houston to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $59 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Houston to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Houston to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from William P. Hobby Airport (HOU) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $59 or cheap return flight from $117 from William P. Hobby Airport (HOU) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from William P. Hobby Airport (HOU) to Midway Intl. Airport (MDW)?
Planning your getaway for February is a good way to save, as it's the cheapest month for flights between HOU and MDW. You'll typically find the lowest prices during the off-season.
Which airlines fly direct from William P. Hobby Airport (HOU) to Midway Intl. Airport (MDW)?
When heading out of William P. Hobby Airport (HOU), you can catch a nonstop flight to Midway Intl. Airport (MDW) with Southwest Airlines.
What is the cheapest airline that flies from William P. Hobby Airport (HOU) to Midway Intl. Airport (MDW)?
To find the cheapest airline that'll fly you from HOU to MDW, use Expedia's filter tool. Tailor your search based on what matters most to you, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
How many flights per day from William P. Hobby Airport (HOU) to Midway Intl. Airport (MDW)?
With an average of 4 nonstop flights that operate from William P. Hobby Airport (HOU) to Midway Intl. Airport (MDW) daily, you'll be off on your next adventure in no time.
What are the most popular departure times for flights from William P. Hobby Airport (HOU) to Midway Intl. Airport (MDW)?
The 8 PM departures from HOU to MDW see the highest demand. These flights can come with a higher price due to their popularity. If you want to save on your trip, choose a less crowded time to fly.
What day of the week has the most flights from HOU to MDW?
Travel on a Friday if you're searching for the best selection of flights from William P. Hobby Airport (HOU) to Midway Intl. Airport (MDW).
What is the earliest flight from William P. Hobby Airport (HOU) to Midway Intl. Airport (MDW)?
Hop on the earliest flight at around 5:55AM UTC-6, departing from William P. Hobby Airport (HOU). You'll be traveling for about 2h 25m, arriving at Midway Intl. Airport (MDW) at approximately 8:20AM UTC-6.
How long does it take to fly from William P. Hobby Airport (HOU) to Midway Intl. Airport (MDW)?
Flights from HOU to MDW have an average travel time of 2 hours and 23 minutes. The distance between these two airports is 940 mi.
What airline has the least delays from HOU to MDW?
With 85% of flights generally arriving on schedule, Southwest Airlines has the best on-time performance for nonstop flights from William P. Hobby Airport (HOU) to Midway Intl. Airport (MDW). To monitor your flight status and get notified about any changes, simply head to the Expedia App.
What is the best time to fly from William P. Hobby Airport (HOU) to Midway Intl. Airport (MDW)?
Select a flight from William P. Hobby Airport (HOU) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the likelihood of delays and cancellations. Later departures have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from William P. Hobby Airport (HOU)?
Midway Intl. Airport (MDW) is the only airport in Chicago with direct flights from William P. Hobby Airport (HOU). Browse the options and discover affordable fares on Expedia.
Is it cheaper to buy a plane ticket from William P. Hobby Airport (HOU) to Midway Intl. Airport (MDW) last-minute?
Last-minute bookings from HOU to MDW are typically more expensive. To secure the best prices, start looking for flights early. That being said, if your travel plans are flexible, you may score a cheap ticket right before your trip.
Is it cheaper to book a HOU to MDW flight and hotel package?
Opting for a HOU to MDW flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Choose from our impressive range of accommodations and then add car rentals, flights and activities to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from William P. Hobby Airport (HOU) to Midway Intl. Airport (MDW)?
If you booked your HOU to MDW flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the ticket type you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more details.

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*Available to One Key members.