$62 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 4/14. 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
$113
Overall average: $215
Spirit Airlines
Sat 4/25Tue 4/28
IAH - ORD • Non-stop
Cheapest one-way
$62
Typical prices: $84-$175
Spirit Airlines
Tue 4/14
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
Expert advice
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Top airlines
Cheapest • from $113 (round-trip)
Best reviews • 8.0 score
Airline reviews
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+1
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Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Frontier and others. Average duration is 2h 38m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 57% average savings
Most popular
Insights
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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 36% 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

Sat, Apr 25 - Tue, Apr 28
Spirit Airlines Logo
2:29 pm - 5:11 pm
IAH
-
ORD
2h 42mnonstop
Spirit Airlines Logo
6:16 pm - 9:10 pm
ORD
-
IAH
2h 54mnonstop
$113Spirit Airlines
Sat, May 2 - Mon, May 4
Multiple Airlines Logo
11:32 am - 2:22 pm
IAH
-
ORD
2h 50mnonstop
Multiple Airlines Logo
6:16 pm - 9:10 pm
ORD
-
IAH
2h 54mnonstop
$122Multiple Airlines
Fri, Apr 24 - Sat, Apr 25
Spirit Airlines Logo
2:29 pm - 5:11 pm
IAH
-
ORD
2h 42mnonstop
Spirit Airlines Logo
6:16 pm - 9:10 pm
ORD
-
IAH
2h 54mnonstop
$123Spirit Airlines
Fri, Apr 17 - Mon, Apr 20
Frontier Logo
9:23 am - 12:13 pm
IAH
-
ORD
2h 50mnonstop
Frontier Logo
5:20 am - 8:27 am
ORD
-
IAH
3h 07mnonstop
$124Frontier
Tue, Apr 21 - Tue, Apr 28
Frontier Logo
6:10 am - 5:00 pm
IAH
-
ORD
10h 50m
1 stop
Frontier Logo
6:08 pm - 4:54 pm
ORD
-
IAH
22h 46m
1 stop
$126Frontier
Tue, Apr 21 - Wed, May 6
Frontier Logo
6:10 am - 10:14 pm
IAH
-
MDW
16h 04m
1 stop
Frontier Logo
6:00 am - 5:03 pm
MDW
-
IAH
11h 03m
1 stop
$126Frontier
Wed, Apr 15 - Tue, Apr 21
Southwest Logo
7:10 am - 9:35 am
HOU
-
MDW
2h 25mnonstop
Southwest Logo
12:15 pm - 2:55 pm
MDW
-
HOU
2h 40mnonstop
$197Southwest
Wed, Apr 15 - Tue, Apr 21
Southwest Logo
7:10 am - 9:35 am
HOU
-
MDW
2h 25mnonstop
Southwest Logo
9:40 am - 2:00 pm
MDW
-
HOU
4h 20m
1 stop
$203Southwest
Wed, Apr 22 - Sat, Apr 25
Delta Logo
5:23 pm - 10:28 pm
HOU
-
MDW
5h 05m
1 stop
Delta Logo
5:21 pm - 11:07 pm
MDW
-
HOU
5h 46m
1 stop
$217Delta
Wed, Apr 22 - Sat, Apr 25
Delta Logo
5:23 pm - 11:59 pm
HOU
-
ORD
6h 36m
1 stop
Delta Logo
5:59 pm - 11:07 pm
ORD
-
HOU
5h 08m
1 stop
$237Delta
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 $49 on the route between Houston George Bush Intcntl Airport (IAH) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 57% 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 January, where tickets cost $166 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is $245 and $237 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 36% 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$62
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 $62 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 4318 reviews
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

I elected to pay for the upgrades and found very little difference

6.0 GoodChris, Mar 2026
DAL - SAT
Read more Southwest reviews

I elected to pay for the upgrades and found very little difference

WiFi was not working and didn’t have a beverage service

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

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.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

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

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

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.

Had to pay for my bag a mini weekender bag 100 dollar fee

The flight was delayed for unknown reasons while other airlines weren’t. It was very frustrating.

Everything was good. On time, boarding fast, flight attendants friendly.

Spirit has always and will always stink. Absolute worst airline around.

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.

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

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.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

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

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.