$63 Find Cheap Flights from Houston to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Houston to Chicago departing on 5/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Houston to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Houston to Chicago.
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Everything you should know

Cheapest round-trip
$113
Typical prices: $355-$167
Frontier
Thu 5/14Tue 5/19
IAH - ORD • Non-stop
Cheapest one-way
$59
Typical prices: $94-$289
Frontier
Tue 5/5
IAH - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest offers two free checked bags, saving costs.
Take the CTA Blue Line from ORD to downtown Chicago.
Expert advice
Expert advice
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Top airlines
Cheapest • from $113 (round-trip)
Best reviews • 8.0 score
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+1
Nonstop flights
You can fly direct with American Airlines, Frontier and others. Average duration is 2h 46m
Direct flights
Direct flights
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+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 46% average savings
Most popular
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Avoid delays
Most punctual • 90% on-time
Best time • Fewest delays
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When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 29% compared to booking last minute.
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Flight Deals

Cheap Flights from Houston to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Houston to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Houston to Chicago

Thu, May 14 - Tue, May 19
Frontier Logo
8:12 pm - 11:01 pm
IAH
-
ORD
2h 49mnonstop
Frontier Logo
4:05 pm - 7:17 pm
ORD
-
IAH
3h 12mnonstop
$113Frontier
Tue, Jun 2 - Thu, Jun 4
Multiple Airlines Logo
7:20 am - 9:59 am
IAH
-
ORD
2h 39mnonstop
Multiple Airlines Logo
4:05 pm - 7:17 pm
ORD
-
IAH
3h 12mnonstop
$114Multiple Airlines
Thu, May 21 - Tue, May 26
Frontier Logo
6:10 am - 7:41 pm
IAH
-
ORD
13h 31m
1 stop
Frontier Logo
4:05 pm - 7:17 pm
ORD
-
IAH
3h 12mnonstop
$115Frontier
Tue, May 19 - Wed, May 20
Frontier Logo
8:12 pm - 11:01 pm
IAH
-
ORD
2h 49mnonstop
Frontier Logo
3:55 pm - 8:50 am
ORD
-
IAH
16h 55m
1 stop
$116Frontier
Sat, May 16 - Mon, May 18
Frontier Logo
8:12 pm - 11:01 pm
IAH
-
ORD
2h 49mnonstop
Frontier Logo
8:30 am - 11:50 am
ORD
-
IAH
3h 20mnonstop
$117Frontier
Wed, May 13 - Tue, May 19
Frontier Logo
8:50 pm - 7:55 am
IAH
-
ORD
11h 05m
1 stop
Frontier Logo
4:05 pm - 7:17 pm
ORD
-
IAH
3h 12mnonstop
$118Frontier
Tue, Jun 2 - Wed, Jun 3
Southwest Logo
8:40 pm - 11:05 pm
HOU
-
MDW
2h 25mnonstop
Southwest Logo
8:40 pm - 11:20 pm
MDW
-
HOU
2h 40mnonstop
$169Southwest
Wed, May 27 - Wed, Jun 3
Southwest Logo
6:10 pm - 8:35 pm
HOU
-
MDW
2h 25mnonstop
Southwest Logo
8:40 pm - 11:20 pm
MDW
-
HOU
2h 40mnonstop
$184Southwest
Wed, Jun 3 - Tue, Jun 9
Delta Logo
1:06 pm - 9:09 pm
HOU
-
MDW
8h 03m
1 stop
Delta Logo
6:00 am - 12:12 pm
MDW
-
HOU
6h 12m
1 stop
$197Delta
Wed, Jun 3 - Tue, Jun 9
Delta Logo
7:00 am - 11:56 am
IAH
-
MDW
4h 56m
1 stop
Delta Logo
6:00 am - 11:23 am
MDW
-
IAH
5h 23m
1 stop
$197Delta
Booking Insights

KAYAK's insights & trends for Houston to Chicago flights

Get data-powered insights and trends into flights from Houston to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Houston to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Houston to Chicago departing in May.

What is the cheapest Houston to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The absolute cheapest return flight from Houston to Chicago costs $94 on the route between Houston George Bush Intcntl Airport (IAH) and Chicago O'Hare Intl Airport (ORD). However, over the past month, flights between Houston George Bush Intcntl Airport (IAH) and Chicago Midway Airport (MDW) were, on average, 46% cheaper than other Houston-Chicago routes. The most popular route is between Houston George Bush Intcntl Airport (IAH) and Chicago O'Hare Intl Airport (ORD).

What’s the cheapest day of the week to fly from Houston to Chicago?

The average price of all round-trip flights from Houston to Chicago clicked on KAYAK for each day over the last 12 months.

When flying from Houston to Chicago, you should consider leaving on a Friday and avoid Mondays if you are looking for the best rates. For your return to Houston, you’ll find the best rates on Thursdays and the most expensive ones on Mondays.

What is the cheapest month to fly from Houston to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Houston to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Houston to Chicago is September, where tickets cost $183 (return) on average. On the other hand, the most expensive months are January and March, where the average cost of round-trip tickets is $738 and $448 respectively.

How far in advance should I book a flight from Houston to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Houston to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Houston to Chicago, you should book around 3 weeks before departure, which saves you about 29% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Expert advice

Expert advice for your flight from Houston to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier, United Airlines and ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Joe Cortez

Joe Cortez

Expert on Spirit Airlines

Joe Cortez is a seasoned managing editor in aviation with over a decade of industry experience. His work has been featured on prominent platforms such as FlyerTalk and TripSavvy, establishing him as a respected voice in aviation journalism.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

John Walton

John Walton

Expert on IAH

Independent aviation journalist John Walton took his first flight at eight weeks old and hasn’t stopped travelling since. A world-renowned expert in airlines and the passenger experience, he writes in depth on aviation, is a resident expert on travel in Japan and France, and offers a uniquely queer perspective on travelling the world.

Good to know

Cheapest flight$59
Flight from Houston George Bush Airport to Chicago O'Hare Airport

When to book flights from Houston to Chicago

Are your dates flexible? Find out the best times to travel from Houston to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Houston to Chicago

  • What is the cheapest flight from Houston to Chicago?

    In the last 3 days, the lowest price for a flight from Houston to Chicago was $59 for a one-way ticket and $113 for a round-trip.

  • Do I need a passport to fly between Houston and Chicago?

    Yes

  • Which airports will I be using when flying from Houston to Chicago?

    Houston has 2 major airports: Houston Hobby and Houston George Bush Intcntl. Chicago is served by 2 airports: Chicago Midway and Chicago O'Hare Intl. You’ll usually find the cheapest deals if you fly from Houston George Bush Airport and land at Chicago O'Hare Airport.

  • Which aircraft models fly most regularly from Houston to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Houston to Chicago?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Houston and Chicago, with SkyTeam being the most commonly used for this route.

  • How does KAYAK find such low prices on flights from Houston to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Houston to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Houston to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Houston is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Houston to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Houston with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Houston to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Houston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Prefer to fly direct from Houston to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Houston to Chicago.
Find which airlines fly direct from Houston to Chicago, which days they fly and book direct flights.

Direct departures

Houston to Chicago

Monday

American Airlines,Frontier,Southwest, +2 more

American Airlines,Frontier, +3 more

Tuesday

American Airlines,Frontier,Southwest, +2 more

American Airlines,Frontier, +3 more

Wednesday

American Airlines,Frontier,Southwest, +2 more

American Airlines,Frontier, +3 more

Thursday

American Airlines,Frontier,Southwest, +2 more

American Airlines,Frontier, +3 more

Friday

American Airlines,Frontier,Southwest, +2 more

American Airlines,Frontier, +3 more

Saturday

American Airlines,Frontier,Southwest, +2 more

American Airlines,Frontier, +3 more

Sunday

American Airlines,Frontier,Southwest, +2 more

American Airlines,Frontier, +3 more

See more direct flights

Direct returns

Chicago to Houston

Monday

American Airlines,Frontier,Southwest, +2 more

American Airlines,Frontier, +3 more

Tuesday

American Airlines,Frontier,Southwest, +2 more

American Airlines,Frontier, +3 more

Wednesday

American Airlines,Frontier,Southwest, +2 more

American Airlines,Frontier, +3 more

Thursday

American Airlines,Frontier,Southwest, +2 more

American Airlines,Frontier, +3 more

Friday

American Airlines,Frontier,Southwest, +2 more

American Airlines,Frontier, +3 more

Saturday

American Airlines,Frontier,Southwest, +2 more

American Airlines,Frontier, +3 more

Sunday

American Airlines,Frontier,Southwest, +2 more

American Airlines,Frontier, +3 more

See more direct flights

Reviews of the top 5 airlines serving from Houston to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Houston to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Houston to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4314 reviews
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

4.0 OkayCrystal, Apr 2026
MSY - MDW
Read more Southwest reviews

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

My first time experience with Spirit Air was not good at all.The reason i did not know to cancel 24Hrs before flight depature you do charge cancellation fee. It's ridiculous policy.Actually you should provide full voucher instead of charging cancellation fee. Confirmation Code# ZNVPHG Thanks Much , Rita S

That this is my second time the they cancel flights and they always wait until the last minute to let people know

Spirit is awful. Do not fly spirit. Nothing but delays, cancellations.

Nothing. We didn’t even have a pilot until one hour after our flight was set to depart and now we are waiting for a gate on a very hot packed aircraft. Spirit has lost its goddamn minds and we will never fly again. On the way down the delay went from 5 minutes to 6 hours to cancelled.

Delayed 11 hours with two being on our destinations tarmac, no compensation or refund and was told I would actually get charged a $200 cancellation fee if I decided to switch airlines for my return flight. For their inconvenience they gave a $10 meal voucher to split between two people in a airport.

Like Spirit but bad that you have to pay for water 🙃

If there are delays, it takes less than a minute for a Spirit employee to make an announcement. It’s very simple.

For a change, friendly staff at check-in and in flight.

Delayed both in takeoff and landing, trash plane no amenities, I've said it before but I'll never fly Spirit again.

It’s was a cheap flight and they got us there safely. It’s just their whole business model that make the experience “meh.” They make you paranoid about whether your personal item is too big. They make you paranoid about being crammed into a middle seat at the back of the plane. They purposely cram people together leaving multiple rows completely empty and even after the door closes the FA’s announce that everyone has to sit in their assigned seat. We knew what we were buying and in that regard we got a cheap and safe flight but it felt like they do their best to take any enjoyment out of the experience. That’s all on management, not the crew.

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Everything you need to know for your flight from Houston to Chicago

Cabin class types available on flights from Houston to Chicago

Cabin classes available on flights from Houston to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.