CHI - HOU

$79 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 9/24. 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 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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Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Hobby

Tue, Sep 23 - Tue, Sep 30
Southwest Logo
6:25 am - 8:55 amMDW-HOU
2h 30mnonstop
Southwest Logo
6:35 am - 9:00 amHOU-MDW
2h 25mnonstop
$157Southwest
Find Deal
Wed, Oct 15 - Mon, Oct 20
Southwest Logo
5:15 am - 7:50 amMDW-HOU
2h 35mnonstop
Southwest Logo
7:30 pm - 9:55 pmHOU-MDW
2h 25mnonstop
$177Southwest
Find Deal
Sat, Sep 27 - Tue, Sep 30
Southwest Logo
2:50 pm - 9:15 pmMDW-HOU
6h 25m1 stop
Southwest Logo
8:55 pm - 11:20 pmHOU-MDW
2h 25mnonstop
$187Southwest
Find Deal
Wed, Sep 24 - Wed, Oct 1
Southwest Logo
6:25 am - 8:55 amMDW-HOU
2h 30mnonstop
Southwest Logo
8:55 pm - 11:20 pmHOU-MDW
2h 25mnonstop
$188Southwest
Find Deal
Sat, Oct 18 - Fri, Oct 24
Delta Logo
6:45 am - 1:27 pmORD-HOU
6h 42m1 stop
Delta Logo
6:44 pm - 11:57 pmHOU-ORD
5h 13m1 stop
$217Delta
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Sat, Nov 8 - Sat, Nov 15
Delta Logo
4:23 pm - 11:00 pmMDW-HOU
6h 37m1 stop
Delta Logo
6:33 pm - 11:32 pmHOU-MDW
4h 59m1 stop
$217Delta
Find Deal
Thu, Sep 25 - Sat, Sep 27
Sun Country Air Logo
8:12 pm - 11:31 amORD-HOU
15h 19m1 stop
Sun Country Air Logo
9:30 am - 8:36 pmHOU-ORD
11h 06m1 stop
$234Sun Country Air
Find Deal
Thu, Sep 25 - Sun, Sep 28
Sun Country Air Logo
8:12 pm - 11:31 amORD-HOU
15h 19m1 stop
Sun Country Air Logo
9:40 am - 5:33 pmHOU-ORD
7h 53m1 stop
$247Sun Country Air
Find Deal
Tue, Sep 30 - Tue, Sep 30
American Airlines Logo
8:25 am - 2:03 pmORD-HOU
5h 38m1 stop
American Airlines Logo
4:26 pm - 9:45 pmHOU-ORD
5h 19m1 stop
$251American Airlines
Find Deal
Wed, Oct 8 - Wed, Oct 15
American Airlines Logo
10:32 am - 6:07 pmORD-HOU
7h 35m1 stop
American Airlines Logo
6:00 am - 10:51 amHOU-ORD
4h 51m1 stop
$261American Airlines
Find Deal
Booking Insights

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.

How much is a round-trip flight from Chicago to Houston Hobby Airport?

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

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Houston Hobby Airport costs $157 on the route between Chicago Midway Airport (MDW) and Houston Hobby Airport (HOU). It is also the most popular route.

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, Thursday 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 October, where tickets cost $165 (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 $256 respectively.

Can I save money by flying with a layover from Chicago to Houston Hobby Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $207 on average.

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, which saves you about 27% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonJune
Cheapest flight$79
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly with an average 20% 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 $79 for a one-way ticket and $157 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 Boeing 737 MAX 8 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 United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Houston are Southwest and United Airlines. With an average price for the route of $337 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $357 and an overall rating of 7.4.

  • 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 $154 or less one-way and $240 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?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Houston Hobby.
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

Reviews of the 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 4243 reviews
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

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

Armrest controller on my seat 35D and nextbooennseat 35E did not work right. Hard to press buttons to recognize and 35D had constantnpressure either upmost down somit was nearly impossible to make selections. .

I flew with my dog and had already purchased my dog’s ticket. Even that morning I had called costumer service to insure that my husband and I had seats together since the website was giving me an error when choosing our seats and the representative mentioned our dog. I showed up early to the airport and when I got to the gate and we started boarding I was help back and told that I was supposed to have a yellow tag and that I should have checked in at the counter for them to give me that tag. I was not aware of this, the representative on the phone did not say anything. Nor did I see it anywhere in the checking process online, so if you travel with a pet and are not checking in luggage, just know that you still have to go to the check in counter when arriving at the airport unless you want to be the last one to board and not have room for your carry on in the overhead bins. Other than that, I had a great experience.

This flight was perfect. No complaints and only the highest regard for the crew and ground staff and how they executed perfectly. I fly a lot with United and would request predictability and transparency in their operations instead of last minute changes.

This is for UA2274 from Houston to Sacramento. The flight was delayed arriving due to mechanical issues so we left about 3 hours later than scheduled. When boarding the plane the temperature inside was excessive - likely close to 100. Pilot apologized and said it was going to improve at altitude, which it did. But before that I honestly thought there might have been more delays removing passengers made ill from the heat. We were delayed leaving due to another mechanical issue. There was not water on the plane due to a panel that was not secured. They did that quickly, but the combination of mechanical issues was rather disturbing and did not reflect well on United.

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

The woman gate agent in Phoenix was none too sympathetic about my check-in process as I am relatively new with using apps. I almost did not get on because she said I did not check-in. I thought I had via Kayak where I purchased a very expensive ticket. Lesson learned but to be told I may not get on as a matter of factly was difficult to hear.

Gate agent did not hold flight for connection, provided no assistance to get new flight

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.

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.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

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.

I didn't order food. I requested a Tomato juice and was given a boody mary mix. The serve needs to warn the customer what their given. It wasn't a huge deal, but I wasted $4.50.

EVERYTHING! It was so bad that I will be filing a claim for reimbursement for my seat as I could not fully sit in it due to an obese person being next to me and spilling over into my "space." And my personal item in the overhead been got crushed between two suitcases, so now my business laptop has been damaged beyond repair. Also, it was expensive! Since you pay for EVERYTHING, the cost of the trip was probably more than if you I used an airline that was not discounted. I will NEVER fly Spirit Airlines again!

One of worst experienc my family have every had with this airline. I was informed my Kayak that my flight was delayed and that my family will not make it to houston for our connecting flight. I contacted Spirit customer service to get my family on a later flight due to the delay in Vagas and them not making their connecting flight. The customer rep keep telling me that the flight from vagas is on time and not delayed. She even make to go to the spirit app on my phone and show me how to look up weather or not the flight was delayed. The app showed "on time" 20 minutes later when my family arrived at the airport for their flight, they were told that the flight was delayed and she will not make her connecting flight. I call spirit airline customer support again that night and spoke to another rep who apologize for his collegue and he told me that my family will receive a credit for this, this was on Saturday I still have not received the credit or an email letting me know when I will be credited for this inconvenience. This is not good business and it need to be fixed.

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

I wanted to upgrade my seat because I’m 6’2 and never have enough leg room for my comfort. They upgraded my seat for free putting me in an emergency exit seat. I was very comfortable

We had an almost 7 hour flight delay. We left the gate twice and taxi-ed and then returned the gate twice. Finally we got a new flight crew (our third one) and then left the gate to the final time before departing at 6:45pm (original flight time was 12pm). Out of Newark.

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

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.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

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

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