$40 Cheap Flights from Houston (IAH) to Chicago (MDW)

View $40 flight on Wed, May 14, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Houston to Chicago (IAH-MDW)

Prices were available within the past 7 days and start at $40 for one-way flights and $80 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Wed, May 14 - Wed, May 21
IAH
Houston
MDW
Chicago
$80 Roundtrip, found 1 hour ago
$80
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, May 14 from Houston to Chicago, returning Wed, May 21, priced at $80 found 1 hour ago
Frontier Airlines
Mon, May 12 - Wed, May 21
IAH
Houston
MDW
Chicago
$115 Roundtrip, found 3 days ago
$115
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, May 12 from Houston to Chicago, returning Wed, May 21, priced at $115 found 3 days ago
Frontier Airlines
Wed, May 14 - Mon, Jun 2
IAH
Houston
MDW
Chicago
$124 Roundtrip, found 12 hours ago
$124
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Wed, May 14 from Houston to Chicago, returning Mon, Jun 2, priced at $124 found 12 hours ago
Frontier Airlines
Fri, May 16 - Wed, May 21
IAH
Houston
MDW
Chicago
$129 Roundtrip, found 1 hour ago
$129
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, May 16 from Houston to Chicago, returning Wed, May 21, priced at $129 found 1 hour ago
Frontier Airlines
Mon, May 12 - Wed, May 21
IAH
Houston
MDW
Chicago
$136 Roundtrip, found 2 days ago
$136
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, May 12 from Houston to Chicago, returning Wed, May 21, priced at $136 found 2 days ago
Frontier Airlines
Mon, May 12 - Wed, May 21
IAH
Houston
MDW
Chicago
$138 Roundtrip, found 2 days ago
$138
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, May 12 from Houston to Chicago, returning Wed, May 21, priced at $138 found 2 days ago
Frontier Airlines
Mon, May 5 - Wed, May 14
IAH
Houston
MDW
Chicago
$139 Roundtrip, found 13 hours ago
$139
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Mon, May 5 from Houston to Chicago, returning Wed, May 14, priced at $139 found 13 hours ago
Frontier Airlines
Mon, May 12 - Wed, May 21
IAH
Houston
MDW
Chicago
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, May 12 from Houston to Chicago, returning Wed, May 21, priced at $142 found 1 day ago
Frontier Airlines
Wed, May 14 - Wed, May 21
IAH
Houston
MDW
Chicago
$144 Roundtrip, found 1 hour ago
$144
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, May 14 from Houston to Chicago, returning Wed, May 21, priced at $144 found 1 hour ago
Delta
Sat, May 17 - Mon, May 19
IAH
Houston
MDW
Chicago
$178 Roundtrip, found 11 hours ago
$178
Roundtrip
found 11 hours ago
Select Delta flight, departing Sat, May 17 from Houston to Chicago, returning Mon, May 19, priced at $178 found 11 hours ago
Flights from Houston (IAH) to Chicago (MDW)
Origin airport
George Bush Intercontinental
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines
Roundtrip price
$80
Distance
918 mi

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 May. 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 $40 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 George Bush Intercontinental Airport (IAH) to Midway Intl. Airport (MDW) cost?
Pick up cheap return fares starting from $104 from George Bush Intercontinental Airport (IAH) 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 Frontier Airlines and Spirit Airlines flight leaving IAH on May 14 2025 and touching down at MDW. The price was last updated on April 23 2025 and has not changed since.
What is the cheapest month to fly from IAH to MDW?
The cheapest flights from IAH 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 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 IAH to MDW?
Right now, the cheapest carrier offering one-way flights from IAH to MDW is Frontier Airlines. You can jet off on this route from $49. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from IAH on May 21 2025. Prices were last updated on April 23 2025 and have not changed since.
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.

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*Available to One Key members.