HOU - ORD

$104 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 10/24. 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, Oct 4 - Mon, Oct 6
Delta Logo
1:13 pm - 7:05 pmHOU-ORD
5h 52m1 stop
Delta Logo
5:51 pm - 11:00 pmORD-HOU
5h 09m1 stop
$207Delta
Find Deal
Wed, Sep 10 - Wed, Sep 17
Southwest Logo
12:40 pm - 10:20 pmHOU-ORD
9h 40m1 stop
Southwest Logo
1:50 pm - 8:05 pmORD-HOU
6h 15m1 stop
$209Southwest
Find Deal
Tue, Sep 30 - Sat, Oct 11
Southwest Logo
12:40 pm - 10:20 pmHOU-ORD
9h 40m1 stop
Southwest Logo
1:30 pm - 10:15 pmORD-HOU
8h 45m1 stop
$213Southwest
Find Deal
Wed, Sep 10 - Wed, Sep 17
Southwest Logo
5:55 am - 11:50 amHOU-ORD
5h 55m1 stop
Southwest Logo
6:15 am - 5:35 pmORD-HOU
11h 20m2 stops
$214Southwest
Find Deal
Sat, Sep 13 - Wed, Sep 17
Delta Logo
10:44 am - 4:31 pmHOU-ORD
5h 47m1 stop
Delta Logo
7:20 am - 12:18 pmORD-HOU
4h 58m1 stop
$217Delta
Find Deal
Tue, Sep 30 - Sat, Oct 4
Southwest Logo
11:25 am - 5:55 pmHOU-ORD
6h 30m1 stop
Southwest Logo
7:00 am - 5:05 pmORD-HOU
10h 05m2 stops
$218Southwest
Find Deal
Fri, Sep 26 - Tue, Sep 30
American Airlines Logo
6:44 pm - 11:59 pmHOU-ORD
5h 15m1 stop
American Airlines Logo
10:03 am - 6:10 pmORD-HOU
8h 07m1 stop
$246American Airlines
Find Deal
Mon, Sep 8 - Wed, Sep 10
American Airlines Logo
2:33 pm - 8:01 pmHOU-ORD
5h 28m1 stop
American Airlines Logo
10:03 am - 6:10 pmORD-HOU
8h 07m1 stop
$258American Airlines
Find Deal
Fri, Sep 5 - Fri, Sep 5
American Airlines Logo
6:00 am - 11:00 amHOU-ORD
5h 00m1 stop
American Airlines Logo
1:20 pm - 8:11 pmORD-HOU
6h 51m1 stop
$301American Airlines
Find Deal
Sun, Sep 7 - Thu, Sep 11
American Airlines Logo
6:22 pm - 11:52 pmHOU-ORD
5h 30m1 stop
American Airlines Logo
10:03 am - 3:59 pmORD-HOU
5h 56m1 stop
$305American Airlines
Find Deal
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.

How much is a round-trip flight from Houston Hobby Airport to Chicago O'Hare Intl Airport?

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 Sundays.

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 September, 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 35% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$104
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 18% 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 $104 for a one-way ticket and $207 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?

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

  • 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 8916 reviews
6.6Food
7.3Comfort
7.1Entertainment
8.1Crew
7.7Boarding
Airline reviews

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.

2.0 MediocreAnonymous, Aug 2025RSW - ORD
Read more United Airlines reviews

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

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

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

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

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

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

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

The first flight was better in terms of the aircraft.

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

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

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

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

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

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

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

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

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

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

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

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

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

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

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

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

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

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

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

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

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

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

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

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

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

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

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

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