$49 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 10/18. 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

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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Houston to Chicago, as well as popular online travel agencies
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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, Oct 23 - Sat, Oct 25
Frontier Logo
9:54 pm - 12:26 amIAH-ORD
2h 32mnonstop
Frontier Logo
1:14 pm - 4:11 pmORD-IAH
2h 57mnonstop
$91Frontier
Find Deal
Thu, Sep 25 - Thu, Oct 2
Frontier Logo
10:08 am - 12:46 pmIAH-MDW
2h 38mnonstop
Frontier Logo
6:30 am - 9:18 amMDW-IAH
2h 48mnonstop
$92Frontier
Find Deal
Fri, Oct 3 - Sat, Oct 4
Spirit Airlines Logo
5:05 pm - 7:50 pmIAH-ORD
2h 45mnonstop
Spirit Airlines Logo
11:57 am - 11:56 pmORD-IAH
11h 59m1 stop
$101Spirit Airlines
Find Deal
Tue, Sep 30 - Fri, Oct 3
Spirit Airlines Logo
10:23 am - 1:09 pmIAH-ORD
2h 46mnonstop
Spirit Airlines Logo
8:56 pm - 11:45 pmORD-IAH
2h 49mnonstop
$102Spirit Airlines
Find Deal
Fri, Oct 3 - Sat, Oct 11
 Logo
8:00 pm - 10:45 pmIAH-ORD
2h 45mnonstop
 Logo
9:27 am - 9:17 pmORD-IAH
11h 50m1 stop
Tue, Sep 30 - Sun, Oct 5
 Logo
10:23 am - 1:09 pmIAH-ORD
2h 46mnonstop
 Logo
11:36 am - 8:15 pmORD-IAH
8h 39m1 stop
Sat, Oct 18 - Mon, Oct 20
Southwest Logo
5:55 pm - 8:20 pmHOU-MDW
2h 25mnonstop
Southwest Logo
9:30 pm - 12:05 amMDW-HOU
2h 35mnonstop
$157Southwest
Find Deal
Fri, Oct 17 - Mon, Oct 27
Southwest Logo
10:25 pm - 12:45 amHOU-MDW
2h 20mnonstop
Southwest Logo
9:30 pm - 12:05 amMDW-HOU
2h 35mnonstop
$161Southwest
Find Deal
Wed, Jan 7 - Fri, Jan 9
American Airlines Logo
9:00 am - 2:25 pmHOU-ORD
5h 25m1 stop
American Airlines Logo
5:00 am - 11:27 amORD-HOU
6h 27m1 stop
$269American Airlines
Find Deal
Wed, Oct 29 - Mon, Nov 3
American Airlines Logo
6:00 am - 10:51 amHOU-ORD
4h 51m1 stop
American Airlines Logo
5:18 am - 11:44 amORD-HOU
6h 26m1 stop
$283American Airlines
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
Southwest offers two free checked bags, saving costs.
Take the CTA Blue Line from ORD to downtown Chicago.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Frontier
Cheapest • from $91 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
IAH-MDW
Cheapest • 65% average savings
IAH-ORD
Most popular
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 35% compared to booking last minute.
Insights
Insights
Insights
Insights
Cheapest round-trip
$91
Typical prices: $125-248
Frontier
Thu 10/23Sat 10/25
IAH - ORD • Non-stop
Cheapest one-way
$49
Typical prices: $56-120
Frontier
Sat 10/18
IAH - MDW • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Expert advice

Expert advice for your flight from Houston to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Frontier

Economy Bundle includes a carry-on bag and seat choice, perfect for budget travelers.


Premium Bundle offers priority boarding and extra legroom, enhancing comfort for a small fee.

Read more about Frontierby Stefanie Waldek
Spirit Airlines

Big Front Seat offers extra legroom and comfort for a nominal fee, ideal for a short flight.


Go Savvy ticket includes a carry-on bag and seat selection, balancing cost and convenience.

American Airlines

Basic Economy offers low fares but includes restrictions like late boarding and no free checked bags.


Main Cabin Extra provides early boarding and complimentary drinks, ideal for a comfortable short flight.

United Airlines

Economy Plus offers extra legroom, enhancing comfort for short flights.


United's Wi-Fi allows gate-to-gate connectivity, ideal for business travelers.

Southwest

Southwest offers free snacks and soft drinks, plus Wi-Fi for streaming on many aircraft.


Southwest's Rapid Rewards program offers unlimited rewards seats and no blackout dates for easy booking.

Read more about Southwestby Blane Bachelor
Airports
IAH

IAH's security lines are standard, with wait times listed on the airport website. Consider alternate terminals if wait exceeds 20-30 minutes.

Read more about IAHby John Walton
ORD

Take the CTA Blue Line from ORD to downtown Chicago for a 45-minute ride, avoiding traffic delays and saving money.

Read more about ORDby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier, United Airlines and ORD

Stefanie Waldek

Stefanie Waldek

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.

Read more
Joe Cortez

Joe Cortez

Expert on Spirit Airlines

Joe Cortez

Joe Cortez

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.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

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.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

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.

Read more
John Walton

John Walton

Expert on IAH

John Walton

John Walton

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.

Read more
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?

What is the cheapest Houston to Chicago flight route?

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

The cheapest return flight from Houston to Chicago costs $75 on the route between Houston George Bush Intcntl Airport (IAH) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 65% 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 Sundays 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 Sundays.

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 October, where tickets cost $168 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $237 and $236 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 35% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Cheapest flight$49
Flight from Houston George Bush Airport to Chicago Midway 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 $49 for a one-way ticket and $91 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 Midway 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?

    Star Alliance is the only airline alliance operating flights between Houston and Chicago.

  • 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, Southwest, United Airlines, +2 more

American Airlines, Southwest, +3 more

Wednesday

American Airlines, Southwest, United Airlines, +2 more

American Airlines, Southwest, +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, Southwest, United Airlines, +2 more

American Airlines, Southwest, +3 more

Wednesday

American Airlines, Southwest, United Airlines, +2 more

American Airlines, Southwest, +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 4242 reviews
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

2.0 MediocreMike, Aug 2025AUS - BWI
Read more Southwest reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

Plz don't take away free bags and free seating

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Spirit is low fare air line. Food also cost you. No free food.

Everyone was kind for the most part. I did travel with children and paid for seats and even then it was not as suitable. I tried calling their customer service prior to check in and I was told they couldn't help me because I didn't purchase my tickets with them.

I think the staff was nice. They took time to explain safety protocols. Boarding was great. They started early and our flight left a little early which was convenient. Having free games to play would have been better

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

Better than my las vagas experience, but still dissapointed with the airline support service.

As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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.

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