$39 Cheap Flights from Houston (IAH) to Chicago (MDW)

View $39 flight on Sat, Oct 18, 2025Opens in a new window

Popular airlines from George Bush Intercontinental Airport (IAH) to Chicago Midway Airport (MDW)

Cheap Flights from Houston to Chicago (IAH-MDW)

Prices were available within the past 7 days and start at $39 for one-way flights and $78 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Nov 8 - Sat, Nov 15
IAH
Houston
MDW
Chicago
$78 Roundtrip, just found
$78
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Nov 8 from Houston to Chicago, returning Sat, Nov 15, priced at $78 just found
Frontier Airlines
Thu, Nov 13 - Sat, Nov 15
IAH
Houston
MDW
Chicago
$88 Roundtrip, just found
$88
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Nov 13 from Houston to Chicago, returning Sat, Nov 15, priced at $88 just found
Frontier Airlines
Sat, Oct 25 - Mon, Oct 27
IAH
Houston
MDW
Chicago
$98 Roundtrip, just found
$98
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Oct 25 from Houston to Chicago, returning Mon, Oct 27, priced at $98 just found
Frontier Airlines
Sat, Nov 8 - Sat, Nov 15
IAH
Houston
MDW
Chicago
$100 Roundtrip, found 6 hours ago
$100
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sat, Nov 8 from Houston to Chicago, returning Sat, Nov 15, priced at $100 found 6 hours ago
Frontier Airlines
Sat, Oct 25 - Fri, Oct 31
IAH
Houston
MDW
Chicago
$105 Roundtrip, found 4 hours ago
$105
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Oct 25 from Houston to Chicago, returning Fri, Oct 31, priced at $105 found 4 hours ago
Frontier Airlines
Thu, Nov 13 - Sat, Nov 15
IAH
Houston
MDW
Chicago
$108 Roundtrip, just found
$108
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Nov 13 from Houston to Chicago, returning Sat, Nov 15, priced at $108 just found
Frontier Airlines
Sat, Nov 1 - Sat, Nov 8
IAH
Houston
MDW
Chicago
$109 Roundtrip, just found
$109
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Nov 1 from Houston to Chicago, returning Sat, Nov 8, priced at $109 just found
Frontier Airlines
Fri, Oct 24 - Sat, Nov 1
IAH
Houston
MDW
Chicago
$114 Roundtrip, found 3 hours ago
$114
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Fri, Oct 24 from Houston to Chicago, returning Sat, Nov 1, priced at $114 found 3 hours ago
Frontier Airlines
Thu, Oct 30 - Sun, Nov 2
IAH
Houston
MDW
Chicago
$115 Roundtrip, just found
$115
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Oct 30 from Houston to Chicago, returning Sun, Nov 2, priced at $115 just found
Frontier Airlines
Sat, Oct 25 - Mon, Oct 27
IAH
Houston
MDW
Chicago
$118 Roundtrip, just found
$118
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Oct 25 from Houston to Chicago, returning Mon, Oct 27, priced at $118 just found

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

October is typically the cheapest month to fly

From $74 - $290 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 $125
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $125

Frequently asked questions

How much does a flight from George Bush Intercontinental Airport (IAH) to Midway Intl. Airport (MDW) cost?
Lock in a cheap one-way flight from $39 or cheap return flight from $78 from George Bush Intercontinental Airport (IAH) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from George Bush Intercontinental Airport (IAH) to Midway Intl. Airport (MDW)?
November is the most affordable month to fly from IAH to MDW. Avoiding peak travel times is often the key to finding a great deal.
Which airlines fly direct from George Bush Intercontinental Airport (IAH) to Midway Intl. Airport (MDW)?
When flying out of George Bush Intercontinental Airport (IAH), you can catch a direct flight to Midway Intl. Airport (MDW) with Frontier Airlines.
What is the cheapest airline that flies from George Bush Intercontinental Airport (IAH) to Midway Intl. Airport (MDW)?
To find the cheapest airline that'll fly you from IAH to MDW, use Expedia's filter tool. Customize your search based on your travel style, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
How many flights per day from George Bush Intercontinental Airport (IAH) to Midway Intl. Airport (MDW)?
On average, George Bush Intercontinental Airport (IAH) has 4 direct flights to Midway Intl. Airport (MDW) each week. If you're looking for more options, use Expedia's filters to look for flights with one or two stops. Fit in a quick visit to another location or just break up your journey.
What are the most popular departure times for flights from George Bush Intercontinental Airport (IAH) to Midway Intl. Airport (MDW)?
More people fly between IAH and MDW at 8 PM than at any other point in the day. Rather go when it's quieter? Travel outside of rush hours and you could save on your ticket as well.
What day of the week has the most flights from IAH to MDW?
Travel on a Friday if you're looking for the biggest selection of flights from George Bush Intercontinental Airport (IAH) to Midway Intl. Airport (MDW).
What is the earliest flight from George Bush Intercontinental Airport (IAH) to Midway Intl. Airport (MDW)?
Catch the earliest flight at around 7:48PM UTC-6, leaving from George Bush Intercontinental Airport (IAH). You'll be in the air for roughly 2h 31m, landing at Midway Intl. Airport (MDW) at approximately 10:19PM UTC-6.
How long does it take to fly from George Bush Intercontinental Airport (IAH) to Midway Intl. Airport (MDW)?
The average flight time from IAH to MDW is 2 hours and 31 minutes, covering a total distance of 920 mi.
What airline has the least delays from IAH to MDW?
Consider traveling with United Airlines if you'd like to go straight from George Bush Intercontinental Airport (IAH) to Midway Intl. Airport (MDW) without any holdups. This carrier has the best track record for punctuality, with an on-time performance of 100%. Want real-time updates? You can keep an eye on your flight status using the Expedia App.
What is the best time to fly from George Bush Intercontinental Airport (IAH) to Midway Intl. Airport (MDW)?
To land at Midway Intl. Airport (MDW) on schedule, choose a flight that leaves from George Bush Intercontinental Airport (IAH) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**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 George Bush Intercontinental Airport (IAH)?
You'll arrive at O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW) when traveling to Chicago on a direct flight from George Bush Intercontinental Airport (IAH).
Is it cheaper to buy a plane ticket from George Bush Intercontinental Airport (IAH) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from IAH to MDW right before your getaway is usually more expensive. But if you're flexible with your schedule, you could bag a cheap last-minute fare.
Is it cheaper to book an IAH to MDW flight and hotel package?
Securing an IAH to MDW flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Pick from our wide range of accommodations and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from George Bush Intercontinental Airport (IAH) to Midway Intl. Airport (MDW)?
If you reserved your IAH to MDW flight in the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you want more information.

Travel information

Origin airport
George Bush Intercontinental
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines
Roundtrip price
$78
Distance
918 mi
Average flight time
2 hours 30 mins

Book with confidence

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 November. 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 $39 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.

 

Houston to Chicago Flights

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*Available to One Key members.