HOU - ORD

$99 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 1/21. 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
$149
Overall average: $197
Southwest
Wed 2/11Wed 2/18
HOU - ORD • 1 stop
Cheapest one-way
$99
Typical prices: $104-$198
Delta
Wed 1/21
HOU - ORD • 1 stop
Top airlines
Delta
Cheapest • from $207 (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 33% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 19% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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

Wed, Feb 11 - Wed, Feb 18
Southwest Logo
6:15 am - 1:30 pm
HOU
-
ORD
7h 15m1 stop
Southwest Logo
11:55 am - 7:50 pm
ORD
-
HOU
7h 55m2 stops
$149Southwest
Wed, Feb 11 - Wed, Feb 18
Southwest Logo
6:15 am - 1:30 pm
HOU
-
ORD
7h 15m1 stop
Southwest Logo
2:15 pm - 8:15 pm
ORD
-
HOU
6h 00m1 stop
$152Southwest
Tue, Jan 20 - Wed, Jan 21
Southwest Logo
7:25 am - 12:15 pm
HOU
-
ORD
4h 50m1 stop
Southwest Logo
11:55 am - 7:40 pm
ORD
-
HOU
7h 45m1 stop
$194Southwest
Wed, Feb 4 - Fri, Feb 6
Southwest Logo
6:15 am - 1:30 pm
HOU
-
ORD
7h 15m1 stop
Southwest Logo
2:15 pm - 8:45 pm
ORD
-
HOU
6h 30m1 stop
$196Southwest
Wed, Jan 21 - Wed, Jan 28
Delta Logo
5:45 am - 1:40 pm
HOU
-
ORD
7h 55m1 stop
Delta Logo
2:50 pm - 10:33 pm
ORD
-
HOU
7h 43m1 stop
$197Delta
Tue, Jan 20 - Wed, Jan 21
Southwest Logo
7:25 am - 12:15 pm
HOU
-
ORD
4h 50m1 stop
Southwest Logo
7:15 am - 5:55 pm
ORD
-
HOU
10h 40m2 stops
$199Southwest
Wed, Feb 4 - Fri, Feb 6
Southwest Logo
12:40 pm - 10:35 pm
HOU
-
ORD
9h 55m2 stops
Southwest Logo
1:45 pm - 8:25 pm
ORD
-
HOU
6h 40m1 stop
$201Southwest
Wed, Feb 11 - Wed, Feb 18
Southwest Logo
7:30 am - 1:00 pm
HOU
-
ORD
5h 30m1 stop
Southwest Logo
11:55 am - 7:50 pm
ORD
-
HOU
7h 55m2 stops
$202Southwest
Sat, Feb 21 - Mon, Feb 23
Delta Logo
10:50 am - 4:54 pm
HOU
-
ORD
6h 04m1 stop
Delta Logo
11:18 am - 4:28 pm
ORD
-
HOU
5h 10m1 stop
$207Delta
Wed, Feb 11 - Wed, Feb 18
Southwest Logo
12:40 pm - 10:35 pm
HOU
-
ORD
9h 55m2 stops
Southwest Logo
11:55 am - 7:50 pm
ORD
-
HOU
7h 55m2 stops
$216Southwest
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 33% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$99
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 20% 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 $149 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 $332 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 $261 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 9073 reviews
7.3Comfort
8.1Crew
7.7Boarding
6.6Food
7.1Entertainment
Airline reviews

Very bad! They kept delaying my flight and wouldn’t do anything about it

2.0 MediocreSalwa, Dec 2025
DAY - ORD
Read more United Airlines reviews

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

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.

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

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.

I stopped flying spirit as much because they are crooks and thieves. It's not like other airlines where you can at least get credits they just take your money.

Flight was on time. Friendly crew. Gate agents in the other hand were very unfriendly.

Bought round trip tickets. Ended up upgrading to first class. Both flights were new planes but hadn’t been equipped with WiFi and there were no charging ports at my seat despite it being new and first class accommodations.

Like: seats that don't move; fast boarding; engaging crew; low-prices; individual gate at LGA; access to restrooms at the gate Dislike: no water on the flight

To be Honest they canceled my flight and didn't have other options. Until 4 says later and I have a 2yr old very disappointed.

The whole thing everything was poorly managed poorly handled spirit doent deserve to be in business period.

Nothing. It was delayed three times and then canceled and we had to drive 15 hours to get home and rent a car.

Always comes in handy when I want a quick weekend getaway.

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

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.

Not clean and was told I would get a great seat and it was not great at all

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

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

Information on your arrival and departure airports