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

View $79 flight on Tue, Nov 18, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Chicago to Houston (MDW-HOU)

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
Wed, Oct 29 - Wed, Nov 5
MDW
Chicago
HOU
Houston
$157 Roundtrip, just found
$157
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Oct 29 from Chicago to Houston, returning Wed, Nov 5, priced at $157 just found

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

October is typically the cheapest month to fly

From $71 - $269 per traveler.

Graph displaying average flight prices per month

Alternative airports near Houston

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

Select flight to George Bush Intercontinental IAH. Cheapest option available. Average driving time to city center is 24 minutes. Flights from $211
IAH
George Bush Intercontinental
Cheapest
Average driving time to city center24 min
Flights from $211
Flights from Chicago (MDW) to Houston (HOU)
Origin airport
Midway Intl.
Destination airport
William P. Hobby
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$157
Distance
937 mi
Average flight time
2 hours 43 mins

Chicago to Houston Flights

The cheapest times to fly from Chicago to Houston

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 Chicago to Houston are during the month of October. You can find some of the cheapest flights from Chicago to Houston with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Houston

Sunday is one of the best days to book for cheap flights from Chicago to Houston: 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 Chicago to Houston

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 Chicago to Houston 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 Chicago to Houston 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 Chicago to Houston 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 Midway Intl. Airport (MDW) to William P. Hobby Airport (HOU) cost?
Snag a cheap one-way flight from $79 or cheap return flight from $157 from Midway Intl. Airport (MDW) to William P. Hobby Airport (HOU) 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 Midway Intl. Airport (MDW) to William P. Hobby Airport (HOU)?
Traveling in October can help you save, as it's the cheapest month for flights between MDW and HOU. You'll usually find the lowest prices during off-peak months.
Which airlines fly direct from Midway Intl. Airport (MDW) to William P. Hobby Airport (HOU)?
You can fly nonstop from Midway Intl. Airport (MDW) to William P. Hobby Airport (HOU) on a Southwest Airlines flight.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to William P. Hobby Airport (HOU)?
Expedia's filter tool lets you easily compare different airlines, departure times and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest MDW to HOU flight.
How many flights per day from Midway Intl. Airport (MDW) to William P. Hobby Airport (HOU)?
When flying out of Midway Intl. Airport (MDW), you can take your pick from an average of 4 daily direct flights to William P. Hobby Airport (HOU).
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to William P. Hobby Airport (HOU)?
Flights between MDW and HOU are their busiest at 8 AM. If you want a less crowded experience and potentially cheaper prices, look for a time when demand is lower.
What day of the week has the most flights from MDW to HOU?
Fly on a Friday if you're searching for the largest selection of flights from Midway Intl. Airport (MDW) to William P. Hobby Airport (HOU).
What is the earliest flight from Midway Intl. Airport (MDW) to William P. Hobby Airport (HOU)?
The earliest flight leaving Midway Intl. Airport (MDW) is at around 5:20AM UTC-6. Catch this flight and you'll reach William P. Hobby Airport (HOU) at approximately 8:15AM UTC-6. The total travel time is 2h 55m.
How long does it take to fly from Midway Intl. Airport (MDW) to William P. Hobby Airport (HOU)?
The average flight time from MDW to HOU is 2 hours and 50 minutes, covering a distance of 940 mi.
What is the best time to fly from Midway Intl. Airport (MDW) to William P. Hobby Airport (HOU)?
Book a flight from Midway Intl. Airport (MDW) to William P. Hobby Airport (HOU) that leaves before 3 PM to reduce the likelihood of delays and cancellations. Departures after this time 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 Houston from Midway Intl. Airport (MDW)?
Catch a direct flight from Midway Intl. Airport (MDW) to Houston and arrive at William P. Hobby Airport (HOU). Another convenient gateway to this destination is George Bush Intercontinental Airport (IAH).
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to William P. Hobby Airport (HOU) last-minute?
Last-minute fares from MDW to HOU are usually more expensive. To lock in the best prices, start looking for flights early. That being said, if you're flexible with your travel plans, it's possible to score a cheap fare right before you leave.
Is it cheaper to book a MDW to HOU flight and hotel package?
You'll generally save money by securing a MDW to HOU flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one place. After choosing your ideal accommodations and flights, you can add extras such as tours, car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to William P. Hobby Airport (HOU)?
In most instances, you can cancel or reschedule your MDW to HOU flight. However, there may be additional fees, especially if your booking was made more than 24 hours ago. Double-check your itinerary for the airline's fees and policies on flight changes, or if you want further information, visit our Customer Service portal.

Explore a world of travel with Expedia

*Available to One Key members.