$79 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 7/4. 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
$133
Typical prices: $358-$220
Frontier
Tue 7/21Thu 7/23
IAH - ORD • Non-stop
Cheapest one-way
$79
Typical prices: $130-$215
Frontier
Sat 7/4
IAH - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Frontier Economy Bundle adds a carry-on and seat choice; AA Basic Economy cuts perks.
United Economy Plus adds legroom, while Frontier Premium Bundle adds boarding.
Expert advice
Expert advice
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Top airlines
Cheapest • from $133 (round-trip)
Best reviews • 7.9 score
Airline reviews
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+1
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+1
Nonstop flights
You can fly direct with American Airlines, Frontier and others. Average duration is 2h 38m
Direct flights
Direct flights
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+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 33% 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 4 weeks in advance save around 37% 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

Tue, Jul 21 - Thu, Jul 23
Frontier Logo
9:58 pm - 12:49 am
IAH
-
ORD
2h 51mnonstop
Frontier Logo
5:46 pm - 9:03 pm
ORD
-
IAH
3h 17mnonstop
$133Frontier
Fri, Jul 17 - Wed, Aug 12
Frontier Logo
9:58 pm - 12:49 am
IAH
-
ORD
2h 51mnonstop
Frontier Logo
5:30 pm - 8:47 pm
ORD
-
IAH
3h 17mnonstop
$134Frontier
Tue, Aug 25 - Tue, Sep 8
Frontier Logo
9:52 pm - 12:42 am
IAH
-
ORD
2h 50mnonstop
Frontier Logo
5:29 pm - 8:57 pm
ORD
-
IAH
3h 28mnonstop
$135Frontier
Wed, Jul 22 - Wed, Jul 29
Frontier Logo
9:58 pm - 12:49 am
IAH
-
ORD
2h 51mnonstop
Frontier Logo
5:46 pm - 9:03 pm
ORD
-
IAH
3h 17mnonstop
$138Frontier
Tue, Aug 25 - Wed, Sep 9
Southwest Logo
2:45 pm - 5:10 pm
HOU
-
MDW
2h 25mnonstop
Southwest Logo
7:50 am - 10:25 am
MDW
-
HOU
2h 35mnonstop
$179Southwest
Tue, Aug 25 - Wed, Sep 9
Southwest Logo
8:50 pm - 11:10 pm
HOU
-
MDW
2h 20mnonstop
Southwest Logo
10:30 am - 1:00 pm
MDW
-
HOU
2h 30mnonstop
$180Southwest
Wed, Aug 26 - Wed, Sep 9
Delta Logo
5:35 pm - 10:36 pm
HOU
-
MDW
5h 01m
1 stop
Delta Logo
6:00 am - 12:04 pm
MDW
-
HOU
6h 04m
1 stop
$199Delta
Tue, Aug 25 - Wed, Aug 26
Delta Logo
6:10 am - 1:10 pm
IAH
-
MDW
7h 00m
1 stop
Delta Logo
10:54 am - 3:42 pm
MDW
-
IAH
4h 48m
1 stop
$199Delta
Sat, Jul 11 - Fri, Jul 17
Multiple Airlines Logo
8:20 am - 10:37 am
IAH
-
RFD
26h 17m
1 stop
Multiple Airlines Logo
7:50 pm - 8:45 am
RFD
-
IAH
12h 55m
1 stop
$364Multiple Airlines
Thu, Jul 30 - Mon, Aug 3
Multiple Airlines Logo
10:09 pm - 8:23 pm
IAH
-
RFD
22h 14m
2 stops
Multiple Airlines Logo
9:13 pm - 1:59 pm
RFD
-
IAH
16h 46m
1 stop
$386Multiple Airlines
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 July.

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 $133 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, 33% 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 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 $173 (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 $451 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 4 weeks before departure, which saves you about 37% 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.

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$79
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 5 days, the lowest price for a flight from Houston to Chicago was $79 for a one-way ticket and $133 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, +1 more

American Airlines,Frontier, +2 more

Tuesday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Wednesday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Thursday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Friday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Saturday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Sunday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

See more direct flights

Direct returns

Chicago to Houston

Monday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Tuesday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Wednesday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Thursday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Friday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Saturday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Sunday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 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.
7.9
SouthwestOverall score based on 4235 reviews
7.0Food
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

I don't know why flying out of Sarasota requires two plane changes.

10.0 ExcellentJohn, Jun 2026
DAL - ABQ
Read more Southwest reviews

I don't know why flying out of Sarasota requires two plane changes.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

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.

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

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.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

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.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

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.

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.