HOU - ORD

$113 Find Cheap Flights from Houston Hobby Airport to Chicago O'Hare Airport - Compare and Save

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 8/19. 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 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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Everything you should know

Cheapest round-trip
$225
Typical prices: $138-$288
Delta
Tue 8/4Wed 8/5
HOU - ORD • 1 stop
Cheapest one-way
$113
Typical prices: $98-$236
Delta
Wed 8/19
HOU - ORD • 1 stop
Top airlines
Cheapest • from $225 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
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Nonstop flights
Not available
There are currently no direct flights between Hobby and O'Hare Intl. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $236 (round-trip)
Shortest trip • 4h 55m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 40% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 26% price drop
Most popular
Good to know
Good to know
+1
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Good to know
Good to know
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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!
Flight Deals
Booking Insights
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

Tue, Aug 4 - Wed, Aug 5
Delta Logo
5:20 pm - 11:57 pm
HOU
-
ORD
6h 37m
1 stop
Delta Logo
6:40 am - 12:16 pm
ORD
-
HOU
5h 36m
1 stop
$225Delta
Wed, Jul 22 - Wed, Aug 5
Delta Logo
5:17 pm - 11:53 pm
HOU
-
ORD
6h 36m
1 stop
Delta Logo
6:40 am - 12:16 pm
ORD
-
HOU
5h 36m
1 stop
$227Delta
Tue, Sep 15 - Tue, Sep 29
Delta Logo
2:25 pm - 8:55 pm
HOU
-
ORD
6h 30m
1 stop
Delta Logo
8:05 am - 1:19 pm
ORD
-
HOU
5h 14m
1 stop
$229Delta
Wed, Aug 12 - Wed, Aug 19
Delta Logo
6:00 am - 4:17 pm
HOU
-
ORD
10h 17m
2 stops
Delta Logo
3:25 pm - 10:05 pm
ORD
-
HOU
6h 40m
1 stop
$230Delta
Tue, Jul 28 - Thu, Aug 27
Delta Logo
12:55 pm - 8:33 pm
HOU
-
ORD
7h 38m
1 stop
Delta Logo
11:22 am - 10:05 pm
ORD
-
HOU
10h 43m
2 stops
$232Delta
Tue, Aug 11 - Tue, Aug 18
Delta Logo
10:50 am - 4:51 pm
HOU
-
ORD
6h 01m
1 stop
Delta Logo
8:48 am - 10:05 pm
ORD
-
HOU
13h 17m
2 stops
$234Delta
Wed, Aug 12 - Tue, Aug 18
Delta Logo
6:00 am - 4:17 pm
HOU
-
ORD
10h 17m
2 stops
Delta Logo
8:48 am - 10:05 pm
ORD
-
HOU
13h 17m
2 stops
$235Delta
Sat, Aug 15 - Mon, Aug 17
Delta Logo
10:50 am - 4:51 pm
HOU
-
ORD
6h 01m
1 stop
Delta Logo
6:40 am - 12:16 pm
ORD
-
HOU
5h 36m
1 stop
$237Delta
Wed, Aug 12 - Tue, Aug 18
Delta Logo
6:00 am - 4:17 pm
HOU
-
ORD
10h 17m
2 stops
Delta Logo
8:48 am - 10:05 pm
ORD
-
HOU
13h 17m
2 stops
$239Delta
Mon, Aug 10 - Tue, Aug 11
Delta Logo
1:13 pm - 6:49 pm
HOU
-
ORD
5h 36m
1 stop
Delta Logo
11:22 am - 10:05 pm
ORD
-
HOU
10h 43m
2 stops
$242Delta
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?

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 Hobby Airport to Chicago O'Hare Intl Airport departing in August.

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 February, where tickets cost $171 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $381 and $284 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 4 weeks before departure, which saves you about 40% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$113
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 64% 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 5 days, the lowest price for a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport was $113 for a one-way ticket and $225 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?

    oneworld, and Star Alliance are the airline alliances operating flights between Houston Hobby Airport and Chicago O'Hare Airport, with oneworld 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 $364 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 7.1.

  • 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 3 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 9908 reviews
7.1Entertainment
7.3Comfort
8.1Crew
7.7Boarding
6.6Food
Airline reviews

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

2.0 MediocreRuss, Jun 2026
FOD - ORD
Read more United Airlines reviews

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Boarded early, left early, arrived 40 mins early! A win win for me!

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

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

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.

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

I don't understand why they can't have charging ports on seats in 2023. They only offer it as a 'premium seat' service. It's ridiculous

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

They lost my baggage and I am still struggling to the information and update

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

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

3hour delay In the last 3 months i had 3 flights and 2 of these had a more than 2:40 hrs delayed

We received a flight delay notification over 24 hours before the flight, but it seems American didn't do anything in that timeframe to get the flight back on schedule. Gate agents were still determining when our plane would arrive. Didn't have catering ready to go when our plane did arrive. Flight attendant timeout before we left. There was a flight attendant on board who could work the flight (trained on that aricraft type and was within hours), however American chose to wait for a backup to arrive, which delay the flight further.

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.

I know that there is nothing than can be done about rude customers. I did find a couple of them were very rude and inconsiderate In my case the guy who was sitting in the same row as I was in, was trying to watch a movie with no headphones, a crew member did ask him to turn it down or off (thumbs up for that.) Another thing, as we were about to land another young man must have taken his phone off airplane mode was talking with his friends and using fowl language which I found inappropriate to the ppl who were sitting in the same row as him and other ppl around him. I understand how no one wanted to address this person and not get involved. We all just wanted to get home safely with out any incident.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

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.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

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

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

We were delayed three times ,and that destroyed my plans, and reservations

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

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

I was singled out for being a Latina flying solo and the attendants took me out of line to put my luggage in the personal item bin to see if it would fly. Keep In mind I had just flown with the same luggage with no problem not even 5 days ago. The tag was sticking out a bit and the attendant was belligerent about charging me $100. I could not refuse because I didn’t wanna cause a scene. But today I felt targeted and embarrassed. I went online and found out that this happens a lot with this airline and to many minority women.

Everything you need to know for your flight from Hobby to O'Hare Intl

Information on your arrival and departure airports