$48 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 3/31. 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, 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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Everything you should know

Cheapest round-trip
$82
Overall average: $203
Frontier
Fri 4/3Mon 4/6
IAH - MDW • Non-stop
Cheapest one-way
$48
Typical prices: $97-$214
Spirit Airlines
Tue 3/31
IAH - ORD • Non-stop
Our travelers' advice
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
Expert advice
Expert advice
Top airlines
Frontier
Cheapest • from $82 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
IAH
-
MDW
Cheapest • 31% 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 33% compared to booking last minute.
Insights
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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

Fri, Apr 3 - Mon, Apr 6
Frontier Logo
1:27 pm - 3:59 pm
IAH
-
MDW
2h 32mnonstop
Frontier Logo
9:20 am - 12:32 pm
MDW
-
IAH
3h 12mnonstop
$82Frontier
Thu, Feb 19 - Thu, Feb 26
Frontier Logo
11:17 am - 2:05 pm
IAH
-
ORD
2h 48mnonstop
Frontier Logo
7:00 am - 10:22 am
ORD
-
IAH
3h 22mnonstop
$84Frontier
Fri, Apr 10 - Mon, Apr 13
Frontier Logo
1:27 pm - 3:59 pm
IAH
-
MDW
2h 32mnonstop
Frontier Logo
9:20 am - 12:32 pm
MDW
-
IAH
3h 12mnonstop
$84Frontier
Fri, Feb 20 - Sun, Feb 22
Multiple Airlines Logo
10:26 am - 1:20 pm
IAH
-
ORD
2h 54mnonstop
Multiple Airlines Logo
8:59 am - 12:00 pm
ORD
-
IAH
3h 01mnonstop
$86Multiple Airlines
Sun, Mar 1 - Wed, Mar 4
Spirit Airlines Logo
5:15 am - 7:54 am
IAH
-
ORD
2h 39mnonstop
Spirit Airlines Logo
9:18 am - 12:24 pm
ORD
-
IAH
3h 06mnonstop
$87Spirit Airlines
Wed, Feb 18 - Sat, Feb 21
Multiple Airlines Logo
4:22 pm - 11:47 pm
IAH
-
ORD
7h 25m
1 stop
Multiple Airlines Logo
8:05 am - 11:29 am
ORD
-
IAH
3h 24mnonstop
$89Multiple Airlines
Tue, Mar 3 - Tue, Mar 10
Southwest Logo
6:40 am - 9:05 am
HOU
-
MDW
2h 25mnonstop
Southwest Logo
6:25 am - 9:15 am
MDW
-
HOU
2h 50mnonstop
$157Southwest
Wed, Mar 4 - Sat, Mar 7
Southwest Logo
6:40 am - 9:05 am
HOU
-
MDW
2h 25mnonstop
Southwest Logo
9:40 pm - 12:25 am
MDW
-
HOU
2h 45mnonstop
$168Southwest
Tue, Feb 24 - Tue, Mar 3
Delta Logo
10:50 am - 4:51 pm
HOU
-
ORD
6h 01m
1 stop
Delta Logo
2:46 pm - 10:28 pm
ORD
-
HOU
7h 42m
1 stop
$197Delta
Tue, Mar 10 - Tue, Mar 17
Delta Logo
5:22 pm - 10:31 pm
HOU
-
MDW
5h 09m
1 stop
Delta Logo
6:00 am - 1:28 pm
MDW
-
HOU
7h 28m
1 stop
$204Delta
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 April.

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 $69 on the route between Houston George Bush Intcntl Airport (IAH) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 31% 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 Fridays 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 February, where tickets cost $150 (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 33% 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$48
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 $48 for a one-way ticket and $82 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, Southwest, Spirit Airlines, +1 more

American Airlines, Southwest, +2 more

Wednesday

American Airlines, Southwest, Spirit Airlines, +1 more

American Airlines, Southwest, +2 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, Spirit Airlines, +1 more

American Airlines, Southwest, +2 more

Wednesday

American Airlines, Southwest, Spirit Airlines, +1 more

American Airlines, Southwest, +2 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 4269 reviews
8.1Boarding
7.0Food
7.5Entertainment
8.6Crew
8.0Comfort
Airline reviews

Great vacation. Can't wait till next year for another one.

10.0 ExcellentJohn, Jan 2026
SAT - PHX
Read more Southwest reviews

Great vacation. Can't wait till next year for another one.

The seats were comfortable, and the boarding process was pretty smooth.

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

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

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Not seat assigned because overbooking. We could go because some people decided to give their seats.

The flights were very uncomfortable the seats don't have much leg room at all and they are pretty hard as well.

Our outgoing flight was cancelled two hours before boarding and Spirit was not able to get us onto another flight. Their customer service was slow and unhelpful.

spirit delayed my first flight 9 hours and then cancelled my flight back home. Very disappointed with their service.

They canceled the flight and didn't assist in getting a new flight on any airline. I had to spend 10 hrs in the airport after getting a ticket On Delta for twice as much. I've flown Spirit many times and this was my worst experience I've had.

Late taking off. ATC sent us circling around Chicago for almost an hour, after landing taxied for 40 minutes.

I waited for 4+ extra hours to even board when i was fighting off a cold. So i was sitting there in the airport with a fever and chills while spirit wasted my time. Then once on the plane we had at least an extra hour of taxiing before and after takeoff. Really poor airline, no amenities to speak of, and a lack of organization that will just ruin your experience.

Terrible. They cancelled the flight at the last minute after I had checked in at the airport and then told me they could only put me on a flight after 7 days. Pathetic.

Flight was on time. Friendly crew. Gate agents in the other hand were very unfriendly.

Bought round trip tickets. Ended up upgrading to first class. Both flights were new planes but hadn’t been equipped with WiFi and there were no charging ports at my seat despite it being new and first class accommodations.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

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.