HOU - ORD

$89 Find Cheap Flights from Houston Hobby Airport to Chicago O'Hare Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hobby to O'Hare Intl departing on 10/31. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
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 Hobby to O'Hare Intl (HOU-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hobby to O'Hare Intl 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 Hobby to O'Hare Intl

Sat, Dec 13 - Tue, Dec 16
Delta Logo
10:39 am - 6:43 pmHOU-ORD
8h 04m1 stop
Delta Logo
5:30 am - 1:28 pmORD-HOU
7h 58m1 stop
$197Delta
Find Deal
Fri, Oct 31 - Sat, Nov 15
Delta Logo
6:44 pm - 11:59 pmHOU-ORD
5h 15m1 stop
Delta Logo
11:17 am - 5:33 pmORD-HOU
6h 16m1 stop
$198Delta
Find Deal
Sat, Nov 8 - Wed, Nov 12
Delta Logo
6:44 pm - 11:58 pmHOU-ORD
5h 14m1 stop
Delta Logo
9:51 am - 5:53 pmORD-HOU
8h 02m1 stop
$199Delta
Find Deal
Thu, Dec 4 - Sat, Dec 6
Delta Logo
6:00 am - 12:10 pmHOU-ORD
6h 10m1 stop
Delta Logo
9:49 am - 5:33 pmORD-HOU
7h 44m1 stop
$207Delta
Find Deal
Thu, Dec 4 - Fri, Dec 5
Southwest Logo
6:20 am - 1:30 pmHOU-ORD
7h 10m1 stop
Southwest Logo
1:45 pm - 7:50 pmORD-HOU
6h 05m2 stops
$222Southwest
Find Deal
Wed, Jan 7 - Fri, Jan 9
Southwest Logo
7:25 am - 12:15 pmHOU-ORD
4h 50m1 stop
Southwest Logo
1:45 pm - 8:25 pmORD-HOU
6h 40m1 stop
$225Southwest
Find Deal
Sat, Nov 1 - Sat, Nov 1
American Airlines Logo
6:00 am - 10:51 amHOU-ORD
4h 51m1 stop
American Airlines Logo
12:03 pm - 6:07 pmORD-HOU
6h 04m1 stop
$243American Airlines
Find Deal
Thu, Dec 4 - Thu, Dec 11
American Airlines Logo
6:29 pm - 11:26 pmHOU-ORD
4h 57m1 stop
American Airlines Logo
5:18 am - 11:45 amORD-HOU
6h 27m1 stop
$250American Airlines
Find Deal
Mon, Nov 24 - Fri, Nov 28
Sun Country Air Logo
7:49 pm - 10:45 amHOU-ORD
14h 56m1 stop
Sun Country Air Logo
11:00 am - 5:25 pmORD-HOU
6h 25m1 stop
$251Sun Country Air
Find Deal
Tue, Nov 25 - Fri, Nov 28
Sun Country Air Logo
6:37 pm - 9:57 amHOU-ORD
15h 20m1 stop
Sun Country Air Logo
11:00 am - 5:25 pmORD-HOU
6h 25m1 stop
$271Sun Country Air
Find Deal

Everything you should know

Top airlines
Delta
Cheapest • from $197 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 31% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 21% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$197
Overall average: $237
Delta
Sat 12/13Tue 12/16
HOU - ORD • 1 stop
Cheapest one-way
$99
Typical prices: $110-$231
Delta
Fri 10/31
HOU - ORD • 1 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 O'Hare Intl!
Booking Insights

KAYAK's insights & trends for Hobby to O'Hare Intl flights

Get data-powered insights and trends into flights from Hobby to O'Hare Intl to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Houston Hobby Airport to Chicago O'Hare Airport?

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

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

What is the cheapest month to fly from Houston Hobby Airport to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Houston Hobby Airport to Chicago O'Hare Intl Airport, 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 Hobby Airport to Chicago O'Hare Intl Airport is August, where tickets cost $179 (return) on average. On the other hand, the most expensive months are April and July, where the average cost of round-trip tickets is $278 and $265 respectively.

How far in advance should I book a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Houston Hobby Airport to Chicago O'Hare Intl Airport, 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 Hobby Airport to Chicago O'Hare Intl Airport, you should book around 3 weeks before departure, which saves you about 31% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$99
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Houston Hobby Airport to Chicago O'Hare Airport

When to book flights from Hobby to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Hobby to O'Hare Intl 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 Houston Hobby Airport to Chicago O'Hare Airport flights

  • What is the cheapest flight from Houston Hobby Airport to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport was $99 for a one-way ticket and $197 for a round-trip.

  • Do I need a passport to fly between Houston Hobby Airport and Chicago O'Hare Airport?

    No, a passport isn't needed to fly from Houston Hobby Airport to Chicago O'Hare Airport. However, local authorities might ask for an official ID.

  • Which aircraft models fly most regularly from Houston Hobby Airport to Chicago O'Hare Airport?

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

  • Which airline alliances offer flights from Houston Hobby Airport to Chicago O'Hare Airport?

    Star Alliance, and oneworld are the airline alliances operating flights between Houston Hobby Airport and Chicago O'Hare Airport, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Houston to Chicago, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Houston to Chicago are United Airlines and American Airlines. With an average price for the route of $354 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $266 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Houston Hobby Airport to Chicago O'Hare Airport?

    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 Hobby Airport to Chicago O'Hare Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport from Houston Hobby Airport 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 Hobby Airport to Chicago O'Hare Airport?

    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 O'Hare Airport with an airline and back to Houston Hobby Airport with another airline. Booking your flights between Houston Hobby Airport and ORD can sometimes prove cheaper using this method.

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

    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 O'Hare Airport from Houston Hobby Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines serving from Hobby to O'Hare Intl

 
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 Hobby to O'Hare Intl? 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.
7.4
United AirlinesOverall score based on 8991 reviews
7.3Comfort
8.1Crew
7.7Boarding
7.1Entertainment
6.6Food
Airline reviews

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

6.0 GoodJerome, Oct 2025IAD - ORD
Read more United Airlines reviews

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

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.

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.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

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

Had to deplane for undisclosed mechanical issue. Landed in Chicago 3 hours late. Food voucher at FLL came just as we were recording. Crew and agents were troopers--better than Spirit last night.

We spent 5 1/2 hours at Ohare cause our flight was diverted cause of rain in the area. We missed appts that we had set on Tuesday and cause we were flying back the next day on the 7am flight we had no time to reschedule anything. Other airlines were landing and taking off fine having no issues. It was only Spirit. Very frustrating flight and I understand why the flights are only around 25-30% full.

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.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

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