Find flights
Deals
Insights
When to book
FAQs & Tips
Airlines

HOU - ORD

$55 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 9/4. 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
0 bags
Sat 8/24
Sat 8/31

Search hundreds of travel sites at once for deals on flights to Chicago O'Hare 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
In the last 7 days travelers have searched 50,552,696 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
9:22 pm - 5:43 pmHOU-ORD
20h 21m1 stop
5:24 pm - 12:07 pmORD-HOU
18h 43m1 stop
$104Frontier
Find Deal
Fri, Aug 23 - Tue, Aug 27
12:57 pm - 10:37 amHOU-ORD
21h 40m1 stop
10:41 am - 7:20 pmORD-HOU
8h 39m1 stop
$105Frontier
Find Deal
Wed, Sep 4 - Mon, Sep 9
12:57 pm - 12:19 pmHOU-ORD
23h 22m1 stop
6:15 am - 12:07 pmORD-HOU
5h 52m1 stop
$110Frontier
Find Deal
Wed, Aug 21 - Wed, Aug 28
12:41 pm - 2:11 amHOU-ORD
13h 30m1 stop
10:47 am - 9:24 amORD-HOU
22h 37m1 stop
$111Frontier
Find Deal
Fri, Aug 23 - Mon, Aug 26
5:05 pm - 11:59 pmHOU-ORD
6h 54m1 stop
3:35 pm - 10:25 pmORD-HOU
6h 50m1 stop
$196Delta
Find Deal
Sat, Oct 5 - Tue, Oct 8
4:16 pm - 11:54 pmHOU-ORD
7h 38m1 stop
3:59 pm - 10:20 pmORD-HOU
6h 21m1 stop
$207Delta
Find Deal
Wed, Aug 14 - Sat, Aug 24
4:27 pm - 9:00 pmHOU-ORD
4h 33m1 stop
1:26 pm - 6:05 pmORD-HOU
4h 39m1 stop
$256American Airlines
Find Deal
Sat, Aug 10 - Tue, Aug 13
2:30 pm - 7:45 pmHOU-ORD
5h 15m1 stop
6:55 pm - 11:52 pmORD-HOU
4h 57m1 stop
$262American Airlines
Find Deal
Wed, Aug 7 - Wed, Aug 14
10:15 am - 8:47 pmHOU-ORD
10h 32m1 stop
10:57 pm - 8:30 amORD-HOU
33h 33m2 stops
Thu, Aug 22 - Thu, Aug 29
10:15 am - 6:12 pmHOU-ORD
31h 57m2 stops
8:05 pm - 11:11 amORD-HOU
15h 06m1 stop
Thu, Aug 22 - Thu, Aug 29

Flights from Hobby to O'Hare Intl - Travel Insights & Trends

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 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 Saturday 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 Wednesdays 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 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 $178 on average. On the other hand, the most expensive months are November and December, where the average cost of tickets is $312 and $308 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
To get a below average price on the flight from Houston Hobby Airport to Chicago O'Hare Intl Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 99 days before departure.

Which airlines provide the cheapest flights from Houston Hobby Airport to Chicago O'Hare Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, Frontier offered the best one-way deal for that route, at $55. KAYAK users also found Houston Hobby Airport to Chicago O'Hare Airport round-trip flights on Frontier from $104 and on Delta from $196.

Good to know

Low season

January

High season

July

Cheapest flight

$55
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 5% lower on average.
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 $55 for a one-way ticket and $104 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.

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

    The two airlines most popular with KAYAK users for flights from Houston to Chicago are American Airlines and Frontier. With an average price for the route of $237 and an overall rating of 7.3, American Airlines is the most popular choice. Frontier is also a great choice for the route, with an average price of $172 and an overall rating of 6.2.

  • 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.

See more FAQs

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 10000 reviews
8.1Crew
7.7Boarding
6.7Food
7.1Entertainment
7.2Comfort
Airline reviews

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

6.0 GoodKate, Jul 2024ATW - ORD
Read more about United Airlines reviews

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

The new Airbus A231neo has neat tech but the economy seats are so tight together that I always had my shoulders against one passenger or the other. I was very miffed that Basic Economy REQUIRES check-in of bags other than your personal carry-on; if you want to offer low-cost airline prices and then add services for a fee, just let me carry on my duffel. Hell, I could have put my carry on IN the duffel and called it a day but the gate agent would not let me; I ended up paying $40 for the risk of losing my bag. Not the worst flight, but far from the best.

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

It was freezing in there. When I asked about it, the response is “we would have to tell them” and then she just walked away and continued to serve beverages. Everyone was cold and they didn’t care at all.

I did not enjoy continuously being lied to about the amount of time we would circle Chicago before deciding to redirect to Milwaukee. Then the amount of time we would sit on the ground in Milwaukee waiting for gas, or to take off again. Or the amount of time it would then take to get to Chicago again, or sit on the runway waiting for a gate. The whole time continuously hopefully we would make our connecting flight that kept getting delayed as well. Only to scramble and miss it. Enough with the BS. Tell me the truth. "Sorry, things are backed up and your probably not going to make your flight. You should rebook on the next flight now rather than wait." You'll never hear those words from an airline. Speaking of which. If the flight has been redirected and/or is seriously delayed, how about making the WiFi free for everyone so they get to rebooking and reserving hotel rooms while still in the air. You've inconvenienced me already and now you want me to pay $20 for Internet so I can try to make other plans. Absolutely disgusting!

Great flight. The captain did a great job of minimizing some minor turbulence and in general it was a smooth flight. Early departure and early arrival at destination. Great service.

Our flight left on time and we arrived a few minutes early. Great service!

Our 9:10 am scheduled flight continued to get delayed all day with no information given from the agents as to why. It wasn’t until I went to the customer service desk and got us switched to another flight at 2:44 pm (that wasn’t nonstop like our booked flight) that the agent finally was able to find out it was due to a fuel leak. I don’t know if our original flight ever took off but I don’t find it acceptable to leave people sitting in an airport all day with no explanation.

I am very disappointed with american. We have flown American airlines numerous times, as well as other airlines and never had such an experience. My son's flight for Sunday afternoon was cancelled around 11 am. We were told not to do anything bec AA would. After an hour of not seeing a change in his flight status. I called AA. I was on hold for half hour then opted for a call back. That call back never came. So I called again, in meantime I started looking online at my options. No flights were leaving that day from AA. But other airlines were flying out. We needed our son in Chicago asap.i kept calling AA for a callback, but never received one. Finally i called back later in the afternoon and a representative answered the call. She told me there were no flights out till Tuesday morning. I asked how this is possible, I had seen flights from AA and other airlines leaving Monday. She said she checked all NYC airports and there were no AA flights till Tuesday AM. Then I asked about getting on another airline. She responded i would be responsible for that. When I asked how AA would reimburse. She became nasty and told me AA has not responsibility to reimburse anything they will put me in a flight for Tuesday morning. When i explained he must be there Monday by 8am, she told me there's nothing to do and practically hung up. At that point I just asked her to book the Tuesday morning flight. I had this experience with other airlines, cancelled due to weather and they and their reps were much more helpful. Either way Tuesday morning flight was delayed as well. Over an hour! I expect more from AA.

When you pay for Premium Economy on an 787 and you’re promised amenities for the extra money, you expect them to work. They didn’t. USB connector wouldn’t charge continuously. 120v outlet wouldn’t hold anything you plugged into it. The adapter would just fall out. The noise canceling headphones stopped noise cancelling in the first 15 minutes for EVERYONE. No one on the plane knew how to fix it so I couldn’t listen to any movies. I just put in my AirPods and went to sleep. Very unhappy with the crappy Panasonic entertainment system. I won’t buy premium again.

Our flight was delayed by 18 hours. Poor accommodations made and no apology.

This flight was awful all around. Delays on the tarmac at PHL before takeoff and at the tarmac in Chicago caused me to miss my final connection. This was completely avoidable, in my opinion.

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

You get what you pay for, but those tickets weren't cheap, so I expected better, but Spirit is just one of those airlines.

Terrible airline. Cancelled the flight less than 24 hours before the flight. Caused me extra expenses!!! This will be the last time me and my family will travel with them

Very long delay of 6hrs with poor communication from airline. Another 5 pm flight to Miami left on time even though ours was scheduled to leave before that at 3. Would only fly Spirit when you have flexibility for cancellations or delays

Horrible They let some flights go while others where grounded or cancelled. Understanding the storm but there is always a way to get it done when you actually care about the people that are not from the place they are leaving from.

Terrible airline, NO REFUNDS!! Only credit for another spirit flight

Cancelled the return flight moments before boarding, horrible customer service in assisting with any rebooking. Never again will I fly Spirit.

Ridiculous that the plane was so late (3+ hours) and blaming weather even though other flights were coming and going. Also gate agent pulled me aside to measure my personal item. My personal item disassembled and fit in the slot. I was told that was unacceptable and I had to throw away the wheels of my pet carrier even though they fit in the slot. Per the gate agent, it had to be 1 piece. That's the spirit of Spirit- screw the customer to try and milk more money out of them.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

Better than expected.on time. Friendly staff in NY however MYR not so nice.

The flight crew and flight attendants are poorly trained and demonstrate poor professionalism. They have a sloppy appearance and communicate with patrons poorly. It is embarrassing for them to be representatives of an airline and for them to be called professionals.

After 5 hours of delay, they cancelled the flight. Very disappointed

My flight to LA was cancelled. I waited at the airport for 3 hrs saying it was delayed and then all of a sudden it was cancelled. Frontier only gave me a voucher and refund but could not rebook me. Flights on other airlines were too expensive last minute. I had to drive down to LA and didn’t even take my return flight home since I had to drive. One of the worst airline experiences in my life. It’s crazy how airlines can just upend people’s plans just like that.

Flying Frontiier was extremely poor!! I paid for a7:15am flight on flight 1601 from PHL To Las Vegas and the delay was brutally, excruciatingly and disgustingly long (8 hrs). I arrived by Uber to PHL at 5:30 am and had to spend the entire 8 hr delay inside the airport. Even more atrocious was that the flight was delayed twice. On the phone with customer service for two hours and was not fully compensated. I feel taken advantage of with this airline. They offered a menial couched for another flight within 90 days to me and my husband who has never flown but this experience has made us almost 100% sure to not fly this airline and will suggest that others don’t either. We don’t want to book ever again, don’t want a menial voucher and I believe by standard and because the flight was delayed for 8 hours, I should be fully reimbursed for the entire round trip. There is no excuse why this should have ever occurred. After sharing my experience with others in Vegas and Philadelphia, I was told that Frontier airlines is notorious for long delayed flights, poor customer service and refusal to compensate people correctly. I’m very nervous to see what departing from Vegas to Philadelphia will bring.

I fly Frontier often and generally don't have any issues. For some reason, the Denver to Houston's George Bush Intercontinental (IAH) flight always needs to wait on the tarmac in Houston because a gate is not available after landing. I've been stuck for as little as 15 minutes and as much as a little over an hour. I know only fly the Frontier Denver to IAH route when there is not an available flight to Houston Hobby (HOU).

Flight was 3 hours late leaving. Poor communication from the staff about delays. Impossible to get in touch with customer service (by design). And it actually didn't come out to be much cheaper than a non-budget airline! Not worth the headache, I'm never flying Frontier again

I’ve never flown frontier without a flight getting canceled. I understand that things go wrong with planes, but all other airlines handle cancellations so well. Frontier becomes a dumpster fire if a problem appears for them.

Checking in was easy and simple, crew was nice and efficient, but I would improve seat assignment randomness to make it easier to sit together based on when you check in. Overall would fly with them again.

Flying Frontier was a nightmare. From the booking through Kayak, checking in, departing and arriving, I will never recommend Kayak or Frontier.

Book cheap flights from Houston to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Houston to Chicago found on KAYAK in the last 72 hours.
9/4Wed
1 stopFrontier
21h 40mHOU-ORD
$55
8/21Wed
1 stopFrontier
23h 22mHOU-ORD
$56
8/20Tue
1 stopDelta
5h 01mHOU-ORD
$98
9/1Sun
1 stopDelta
5h 12mHOU-ORD
$108
9/1Sun
1 stopAmerican Airlines
7h 39mHOU-ORD
$127
8/10Sat
1 stopAmerican Airlines
4h 33mHOU-ORD
$128
9/22Sun
1 stopSun Country Air
8h 18mHOU-ORD
$130
8/11Sun
1 stopSun Country Air
22h 43mHOU-ORD
$138
8/2Fri
2 stops
20h 43mHOU-ORD
$159
8/11Sun
2 stops
16h 12mHOU-ORD
$171

Search by stops

Search by airline

Search by price

Last minute flights from Hobby to O'Hare Intl

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Houston to Chicago that are departing in the next 10 days.
7/26Fri
multi-stopFrontier
24h 36mHOU-ORD
8/29Thu
multi-stopFrontier
26h 36mORD-HOU
$276
7/30Tue
multi-stopFrontier
9h 20mHOU-ORD
8/6Tue
multi-stopFrontier
8h 25mORD-HOU
$308
7/30Tue
multi-stopFrontier
9h 20mHOU-ORD
8/6Tue
multi-stopFrontier
8h 25mORD-HOU
$329
7/30Tue
multi-stopFrontier
9h 20mHOU-ORD
8/6Tue
multi-stopFrontier
8h 25mORD-HOU
$359
7/29Mon
multi-stopSouthwest
4h 35mHOU-ORD
8/1Thu
multi-stopSouthwest
7h 05mORD-HOU
$474
7/27Sat
multi-stopAmerican Airlines
5h 48mHOU-ORD
8/29Thu
multi-stopAmerican Airlines
4h 39mORD-HOU
$493
7/27Sat
multi-stopAmerican Airlines
5h 36mHOU-ORD
7/31Wed
multi-stopAmerican Airlines
4h 36mORD-HOU
$523
7/26Fri
multi-stopDelta
8h 07mHOU-ORD
7/31Wed
multi-stopDelta
5h 05mORD-HOU
$579
7/30Tue
multi-stopDelta
5h 45mHOU-ORD
8/11Sun
multi-stopDelta
5h 18mORD-HOU
$589
7/26Fri
multi-stopSouthwest
6h 20mHOU-ORD
7/28Sun
multi-stopSouthwest
7h 35mORD-HOU
$650

Search by stops

Search by airline

Search by price

Houston Hobby Airport - Chicago O'Hare Airport Flights

Departure:

Houston Hobby Airport (HOU)United States

Destination:

Chicago O'Hare Airport (ORD)United States

Return flight deals:

Chicago O'Hare Airport - Houston Hobby Airport

Cabin classes: