CHI - HOU

$90 Find Cheap Flights from Chicago to Houston Hobby 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 Chicago to Hobby departing on 7/1. 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.
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KAYAK searches hundreds of travel sites at once for deals on flights to Houston Hobby Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Houston, 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 Chicago to Houston, as well as popular online travel agencies
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Flights Deals

Cheap Flight Deals from Chicago to Hobby (CHI-HOU)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Hobby 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.

Recent round-trip flight deals from Chicago to Hobby

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Hobby.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
9:40 pm - 12:10 amMDW-HOU
2h 30mnonstop
Southwest Logo
1:35 pm - 4:05 pmHOU-MDW
2h 30mnonstop
$179Southwest
Find Deal
Tue, Jul 1 - Fri, Jul 4
Southwest Logo
5:15 am - 11:10 amMDW-HOU
5h 55m1 stop
Southwest Logo
1:35 pm - 4:05 pmHOU-MDW
2h 30mnonstop
$189Southwest
Find Deal
Tue, Jul 1 - Fri, Jul 4
Southwest Logo
6:10 am - 8:50 amMDW-HOU
2h 40mnonstop
Southwest Logo
8:20 pm - 10:50 pmHOU-MDW
2h 30mnonstop
$197Southwest
Find Deal
Sat, May 31 - Tue, Jun 3
Delta Logo
9:40 am - 5:44 pmORD-HOU
8h 04m1 stop
Delta Logo
6:00 am - 12:30 pmHOU-ORD
6h 30m1 stop
$217Delta
Find Deal
Sat, Jun 14 - Sat, Jun 21
Delta Logo
1:30 pm - 9:17 pmORD-HOU
7h 47m1 stop
Delta Logo
6:41 pm - 11:58 pmHOU-ORD
5h 17m1 stop
$225Delta
Find Deal
Sat, Jun 7 - Fri, Jun 13
American Airlines Logo
1:28 pm - 7:53 pmORD-HOU
6h 25m1 stop
American Airlines Logo
8:23 pm - 12:59 amHOU-ORD
4h 36m1 stop
$257American Airlines
Find Deal
Wed, Jul 2 - Sun, Jul 6
American Airlines Logo
1:58 pm - 7:44 pmORD-HOU
5h 46m1 stop
American Airlines Logo
6:31 pm - 11:56 pmHOU-ORD
5h 25m1 stop
$263American Airlines
Find Deal
Wed, May 21 - Wed, Jun 4
Sun Country Air Logo
7:00 am - 5:33 pmORD-HOU
10h 33m1 stop
Sun Country Air Logo
6:42 pm - 5:09 pmHOU-ORD
22h 27m1 stop
$275Sun Country Air
Find Deal
Sun, Jun 1 - Sun, Jun 8
Sun Country Air Logo
8:05 pm - 11:33 amORD-HOU
15h 28m1 stop
Sun Country Air Logo
9:10 am - 5:27 pmHOU-ORD
8h 17m1 stop
$308Sun Country Air
Find Deal
Thu, May 15 - Sun, May 18
 Logo
7:30 pm - 9:06 pmORD-HOU
25h 36m1 stop
 Logo
6:30 pm - 11:59 pmHOU-ORD
29h 29m2 stops
Fri, Jun 13 - Fri, Jun 20
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KAYAK's insights & trends for Chicago to Hobby flights

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

Find cheap flights to Houston Hobby Airport
Find cheap flights to Houston Hobby Airport

Planning a trip from Chicago to Hobby? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.

What is the cheapest Chicago to Houston Hobby Airport flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Houston Hobby Airport.

Our data shows that the cheapest route for a return flight from Chicago to Houston Hobby Airport cost $177 and was between Chicago Midway Airport (MDW) and Houston Hobby Airport (HOU). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $177.

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

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

For Chicago to Houston Hobby Airport, Friday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Houston Hobby Airport back to Chicago, the best deals are generally found on Friday, with Sunday being the most expensive.

What is the cheapest month to fly from Chicago to Houston Hobby Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Houston Hobby 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 Chicago to Houston Hobby Airport is August, where tickets cost $152 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $264 and $259 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Houston Hobby 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 Chicago to Houston Hobby Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonJanuary
High seasonMarch
Cheapest flight$90
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 31% increase in price.
Flight from Chicago Midway Airport to Houston Hobby Airport

When to book flights from Chicago to Hobby

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

  • Which accommodation options are available at Hobby Airport?

    Located 1 mile away from the airport are luxurious hotels like the Days Inn & Suites, the DoubleTree by Hilton, Hampton Inn, and Holiday Inn, which provide cozy accommodations. The hotels also offer complimentary shuttles.

  • Does O'Hare Airport have disabled-friendly amenities?

    O'Hare Airport accommodates the needs of those with special needs and disabilities by providing amenities like elevators, Braille, accessible parking spots at lots B, C, D, F. G, H with ramps and elevators close by, operator-assisted phones in T2, T3, and T5, and mobility assistance.

  • What kind of public transportation can I use to get to Midway Airport from downtown Chicago?

    There is a regular and affordable train service—the Orange Line—that transports travelers from Downtown Chicago to MDW. Orange-Line trains take between 20min and 25min to complete the journey and charge around $2.50.

  • Does Midway Airport have lounges?

    Midway Airport has only one lounge, the USO lounge in Concourse C, which is open to those actively serving in the military and their families free of charge. The cozy lounge is equipped with gaming stations, a kitchenette with complimentary refreshments, TVs, and reading materials.

  • What is the cheapest flight from Chicago to Houston Hobby Airport?

    In the last 3 days, the lowest price for a flight from Chicago to Houston Hobby Airport was $90 for a one-way ticket and $179 for a round-trip.

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

    A passport is not required to fly from Chicago to Houston Hobby Airport.

  • Which airports will I be using when flying from Chicago to Houston Hobby Airport?

    When flying out of Chicago you will be using one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be landing at Houston Hobby.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Houston Hobby Airport?

    Only American Airlines offers inflight Wi-Fi service on the Chicago to Houston Hobby Airport flight route.

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

    The Airbus A321neo is the aircraft model that flies most regularly on the Chicago to Houston Hobby Airport flight route.

  • On which days can I fly direct from Chicago to Houston Hobby Airport?

    There are nonstop flights from Chicago to Houston Hobby Airport on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Houston are Southwest and American Airlines. With an average price for the route of $378 and an overall rating of 8.0, Southwest is the most popular choice. American Airlines is also a great choice for the route, with an average price of $258 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Chicago to Houston Hobby 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 Chicago to Houston Hobby Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Houston Hobby Airport from Chicago 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 Chicago to Houston Hobby 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 Houston Hobby Airport with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Houston Hobby 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 Houston Hobby Airport from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Houston Hobby Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $118 or less one-way and $263 or less round-trip.
  • Travelers can get nonstop flights to Hobby Airport (HOU) from Midway Airport (MDW) with Southwest Airlines. O'Hare Airport (ORD), which serves as a hub for United and American Airlines, also operates nonstop flights to Hobby Airport through both airlines.
  • O'Hare Airport provides tranquil spaces in their sophisticated lounges to ensure travelers get some much-needed relaxation time before their flights. The United Airlines United Club, located in Terminal 2, is one such lounge that one can access by paying around $59.
  • If you choose to drive yourself to Midway Airport, you can leave your vehicle at one of the long-term parking lots. The economy lot, which you will find on the northwest side of the terminal, provides convenient and affordable long-term parking at a rate of about $15. Free shuttles are available from the parking lot.
  • Hobby Airport provides families with essential amenities to ensure they have a stress-free time while at the airport. There is a children's play area in the west concourse. The airport also has two mothers'rooms situated right next to Gate 46 and Gate 4.
  • Travelers arriving at Hobby Airport can find Metro bus 40, which stops right outside the arrivals area. The Metro bus takes approximately 60min to travel from Hobby Airport to downtown Houston. The standard fare for the one-way trip is around $1.25.
  • Midway Airport has plenty of paintings, exhibits, sculptures, and murals spread all over the airport to give travelers a one-of-a-kind traveling experience. On the Mezzanine level of Midway Airport is the hanging sculpture that poetically links human-made and natural aviation.
  • Taking the GO Airport shuttle is a convenient way to travel from O'Hare Airport to downtown Chicago. Only passengers with one suitcase of standard size and one hand luggage are allowed onboard the shuttle. The standard fare for the shuttle trip, which takes approximately 45min, is around $30.

Prefer to fly direct from Chicago to Houston Hobby Airport?

Find which airlines fly direct from Chicago to Houston Hobby Airport, which days they fly and book direct flights.

Direct departures

Chicago to Houston Hobby

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Houston Hobby to Chicago

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Top 5 airlines serving from Chicago to Hobby

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Houston. 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 Chicago to Hobby? 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.
8.0
SouthwestOverall score based on 4293 reviews
8.6Crew
8.2Boarding
7.6Entertainment
7.1Food
8.0Comfort
Airline reviews

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

10.0 ExcellentReginald, Mar 2025MDW - LGA
Read more Southwest reviews

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

First, my flight was a usual flight nothing exceptional or unexpected. Over all it was a normal, good flight! Second, your questionaire is wholly lacking in the proper options to which one can answer a question. Often on short flights, there is no food let alone entertainment so why isn't that reflected in your questionaire? A simple "not applicable" would cover that issue appropriately but no, your form arbitrarily enters an answer based on the initial assessment which normally isn't factual. Until you provide an accurate means of assessing flights, I'll no longer be completing of these unimpressive and misleading assessements. Thank you!

Easy to book and to get check in and get on and off.

Excellent experience. WiFi worked on this leg of My trip

First time I’ve ever missed a flight and it was an international flight.. Southwest put me on the next flight and it was the best experience possible.

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My suitcase was destroyed. The top part where the handle is is completed broken. And unusable now.

Since when do I have to pay for my checked bag? I have a United Explorer mileage plus silver card and I was charged for my checked bags. This also is an international flight. So I would like an explanation to be clear before I choose an airline please?

Michael, our FA was very attentive, even finding me a chocolate brownie from economy class when the dessert selections were all dairy based. ( intolerant, not allergic so don’t usually need to order dairy free)

I don’t understand the purpose of the orange “priority” tag on my bag. This tagged, my bag is last or near to the last bag to come down the carousel at IAH.

Oh my gosh, I loved my experience with United! they made me want to travel more often.

The planes are so dirty! Food crumbs and finger print smudges, Dust over the vents and carpet stains. It’s disgusting.

The bag drop personal were not helpful. There was no food on the flight. Boeing aircraft, lousy as always. Everything else was fine.

Asked several times dairy free options and was ignored. Was told chips was the only thing I could have that I should have put it on my profile “which it is”. Very unprofessional. WiFi didn’t work have the flight. Overall a very bad experience.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

WiFi could have been a little more consistent - otherwise a phenomenal and positive experience. The 1000 mile giveaway was awesome!!!

Your employees need to learn how to talk to people as creations of Yah. We are not their children nor are we lower than them.

Helpful attendants at check-in is very good. The $70 charge for a checked bags I didn't care for.and the constant charges for picking a seat and faster check-in are too much. Please cut the prices by at least 50% would be fantastic!

The flight was delayed over an hour and we had to sit on the plane. Crew does not apologize due to the delay. Spirit will NEVER do anything to give a customer a better experience. A child next to me was kicking me the whole time. I don't ever enjoy flying with Spirit.

Flight was ok with exception of the multiple delays. As with all Spirit flights, the sights are extremely uncomfortable and lack leg space. However, the price savings is the plus.

Easy! As long as you don’t mind no frills, our flight was enjoyable and on time

Okay for the most part but Good boarding and on time

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

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