$79 Cheap Flights from Houston (HOU) to Chicago (MDW)

View $79 flight on Tue, Oct 21, 2025Opens 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 $79 for one-way flights and $157 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Sep 30 - Sat, Oct 4
HOU
Houston
MDW
Chicago
$157 Roundtrip, just found
$157
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Sep 30 from Houston to Chicago, returning Sat, Oct 4, priced at $157 just found
Southwest Airlines
Thu, Oct 9 - Mon, Oct 13
HOU
Houston
MDW
Chicago
$167 Roundtrip, found 3 days ago
$167
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Oct 9 from Houston to Chicago, returning Mon, Oct 13, priced at $167 found 3 days ago
Southwest Airlines
Thu, Oct 30 - Mon, Nov 3
HOU
Houston
MDW
Chicago
$172 Roundtrip, found 3 days ago
$172
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Oct 30 from Houston to Chicago, returning Mon, Nov 3, priced at $172 found 3 days ago
Southwest Airlines
Sat, Sep 6 - Sun, Sep 7
HOU
Houston
MDW
Chicago
$177 Roundtrip, just found
$177
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Sep 6 from Houston to Chicago, returning Sun, Sep 7, priced at $177 just found
Southwest Airlines
Thu, Oct 9 - Mon, Oct 13
HOU
Houston
MDW
Chicago
$182 Roundtrip, found 3 days ago
$182
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Oct 9 from Houston to Chicago, returning Mon, Oct 13, priced at $182 found 3 days ago
Delta
Sat, Sep 13 - Wed, Sep 17
HOU
Houston
MDW
Chicago
$187 Roundtrip, found 4 hours ago
$187
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Sep 13 from Houston to Chicago, returning Wed, Sep 17, priced at $187 found 4 hours ago
Southwest Airlines
Mon, Oct 20 - Tue, Oct 21
HOU
Houston
MDW
Chicago
$188 Roundtrip, found 1 hour ago
$188
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Mon, Oct 20 from Houston to Chicago, returning Tue, Oct 21, priced at $188 found 1 hour ago
Southwest Airlines
Thu, Oct 9 - Sat, Oct 11
HOU
Houston
MDW
Chicago
$192 Roundtrip, found 3 days ago
$192
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Oct 9 from Houston to Chicago, returning Sat, Oct 11, priced at $192 found 3 days ago
Southwest Airlines
Tue, Sep 30 - Sat, Oct 4
HOU
Houston
MDW
Chicago
$197 Roundtrip, just found
$197
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Sep 30 from Houston to Chicago, returning Sat, Oct 4, priced at $197 just found
Southwest Airlines
Sat, Sep 6 - Sun, Sep 7
HOU
Houston
MDW
Chicago
$198 Roundtrip, just found
$198
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Sep 6 from Houston to Chicago, returning Sun, Sep 7, priced at $198 just found

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

October is typically the cheapest month to fly

From $69 - $348 per traveler.

Graph displaying average flight prices per month

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 $188
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $188
Flights from Houston (IAH) to Chicago (MDW)
Origin airport
George Bush Intercontinental
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$95
Distance
918 mi
Average flight time
2 hours 26 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 September. 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 $79 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 cheap return flights starting at $111 from William P. Hobby Airport (HOU) to Midway Intl. Airport (MDW). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and Spirit Airlines flight leaving HOU on August 16 2025 and touching down at MDW. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from HOU to MDW?
The cheapest flights from HOU to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 HOU to MDW?
Currently, the cheapest airline offering one-way flights from HOU to MDW is Southwest Airlines. You can book a seat on this route from $79. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from HOU on October 16 2025. Prices were last updated on July 23 2025 and have not changed since.
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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