HOU - CHI

$79 Find Cheap Flights from Houston Hobby Airport to Chicago

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 Chicago departing on 9/16. 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

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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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Cheap Flights from Hobby to Chicago (HOU-CHI)

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

Sat, Sep 13 - Sat, Sep 20
Southwest Logo
8:20 pm - 10:45 pmHOU-MDW
2h 25mnonstop
Southwest Logo
7:20 pm - 9:50 pmMDW-HOU
2h 30mnonstop
$157Southwest
Find Deal
Tue, Sep 9 - Tue, Sep 16
Southwest Logo
1:25 pm - 3:50 pmHOU-MDW
2h 25mnonstop
Southwest Logo
9:10 am - 11:45 amMDW-HOU
2h 35mnonstop
$173Southwest
Find Deal
Sat, Sep 13 - Mon, Sep 15
Southwest Logo
8:20 pm - 10:45 pmHOU-MDW
2h 25mnonstop
Southwest Logo
8:45 pm - 11:15 pmMDW-HOU
2h 30mnonstop
$177Southwest
Find Deal
Sat, Sep 20 - Mon, Sep 22
Southwest Logo
8:20 pm - 10:45 pmHOU-MDW
2h 25mnonstop
Southwest Logo
8:45 pm - 11:15 pmMDW-HOU
2h 30mnonstop
$187Southwest
Find Deal
Sat, Sep 20 - Mon, Sep 22
Southwest Logo
8:20 pm - 10:45 pmHOU-MDW
2h 25mnonstop
Southwest Logo
5:25 am - 9:40 amMDW-HOU
4h 15m1 stop
$197Southwest
Find Deal
Sat, Oct 4 - Mon, Oct 6
Delta Logo
1:13 pm - 7:05 pmHOU-ORD
5h 52m1 stop
Delta Logo
5:51 pm - 11:00 pmORD-HOU
5h 09m1 stop
$207Delta
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Sat, Sep 6 - Tue, Sep 9
Delta Logo
10:22 am - 3:28 pmHOU-MDW
5h 06m1 stop
Delta Logo
4:25 pm - 10:31 pmMDW-HOU
6h 06m1 stop
$217Delta
Find Deal
Mon, Nov 24 - Fri, Nov 28
Sun Country Air Logo
7:49 pm - 10:45 amHOU-ORD
14h 56m1 stop
Sun Country Air Logo
11:00 am - 5:25 pmORD-HOU
6h 25m1 stop
$239Sun Country Air
Find Deal
Sat, Sep 27 - Sat, Oct 4
American Airlines Logo
6:44 pm - 11:59 pmHOU-ORD
5h 15m1 stop
American Airlines Logo
10:01 am - 6:10 pmORD-HOU
8h 09m1 stop
$256American Airlines
Find Deal
Fri, Sep 5 - Fri, Sep 5
American Airlines Logo
6:00 am - 11:00 amHOU-ORD
5h 00m1 stop
American Airlines Logo
1:20 pm - 8:11 pmORD-HOU
6h 51m1 stop
$301American Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Hobby to Chicago flights

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

Find cheap flights to Chicago
Find cheap flights to Chicago

Planning a trip from Hobby to Chicago? 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 Houston Hobby Airport to Chicago?

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

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

The cheapest return flight from Houston Hobby Airport to Chicago costs $93 on the route between Houston Hobby Airport (HOU) and Chicago Midway Airport (MDW). It is also the most popular route.

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

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

Your flight ticket price will generally be cheaper if you fly to Chicago on a Friday and more expensive on a Sunday. On your return trip to Houston Hobby Airport, you should consider flying back on a Thursday, and avoid Sundays for better deals.

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

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, 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 is September, where tickets cost $162 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $237 and $236 respectively.

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

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.

No, with an average price for the route of $280, prices are generally cheapest when you fly direct.

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

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, 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, you should book around 3 weeks before departure, which saves you about 35% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$79
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 17% lower on average.
Flight from Houston Hobby Airport to Chicago Midway Airport

When to book flights from Hobby to Chicago

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

  • Do Chicago airports have accommodation?

    Travelers can relax and unwind at some of the luxury hotels located within Midway Airport, like Residence Inn Midway Airport hotel located just 1 mile away from the terminal. You can stay at the Hilton O'Hare Airport Hotel right across T1, T2, and T3.

  • Does Houston Hobby Airport have services for passengers with limited mobility?

    Those with limited mobility can receive baggage and wheelchair assistance from Skycap Service. The airport also has wheelchair-accessible restrooms and elevators. Those with disabilities should communicate any other assistance they may require through the airline before their departure date.

  • What family-friendly facilities do Chicago airports have?

    There is a nursing room on Concourse C at Midway Airport. Most restrooms at Midway Airport have baby-changing stations. You will also find kid-friendly restaurants at the airport. There is a kids'play area in Terminal 2 of O'Hare Airport. Nursing rooms are also available at Terminals 1 to 5.

  • Does Hobby Airport have affordable parking options?

    An affordable parking lot at Hobby Airport is the Ecopark, where you can leave your car for a fee of around $9. Another option is the Terminal Parking garage, which charges around $13 for the daily parking option. Valet parking is also available for around $28 per day.

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

    In the last 3 days, the lowest price for a flight from Houston Hobby Airport to Chicago was $79 for a one-way ticket and $157 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

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

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

    American Airlines, JetBlue, Delta, and Alaska Airlines offer inflight Wi-Fi service on the Houston Hobby Airport to Chicago flight route.

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

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Houston Hobby Airport to Chicago flight route.

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

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

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

    The two airlines most popular with KAYAK users for flights from Houston to Chicago are Southwest and American Airlines. With an average price for the route of $282 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 $269 and an overall rating of 7.2.

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

    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.

  • 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?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago 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?

    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 with an airline and back to Houston Hobby Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Houston Hobby Airport to Chicago?

    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 from Houston Hobby Airport 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 Houston Hobby Airport to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $188 or less one-way and $188 or less round-trip.
  • If you intend to fly from Houston's Hobby Airport (HOU) to Chicago's Midway Airport (MDW) without having layovers during the trip, you can get a flight operated by Southwest Airlines. If you do not mind a layover, you can use Delta Air Lines.
  • If you’re looking for a convenient transportation means from Downtown Houston to Hobby Airport, you should book the airport shuttles, which charge a minimum fare of around $19. The shuttles will drop you off outside the baggage claim. The cheaper alternative is the 73 Bellfort Metro, which charges around $1.25.
  • Several amenities at Chicago Midway Airport make traveling through the airport easier for those with limited mobility. Elevators have raised letters and braille, family assisted care restrooms, wheelchair-accessible telephone booths, and wheelchair escorts.
  • Exploring the vibrant Chicago city in a rental car will not only be convenient but will give you maximum flexibility. Midway Airport has several car rentals, like Enterprise, located on Level 2 of the airport's parking garage. The Avis desk is located on Level 3.
  • If you have plenty of time to kill before your flight, you can explore some of Hobby Airport's famous attractions, like the museum located at the airport's terminal, or marvel at the art deco design, which reflects Houston's Aviation era.
  • If you fly in from Houston, landing at Chicago Midway Airport provides more convenience than landing at the bustling O'Hare Airport (ORD). Because Midway is relatively smaller, you can expect shorter lines and faster service. Midway Airport is also closer to Downtown Chicago than O'Hare Airport.
  • From Chicago O'Hare Airport, you can board the Blue Line L train, which takes around 45min to reach Downtown Chicago. You can find the L Train, which charges a minimum rate of approximately $5 at either Terminal 1, Terminal 2, or Terminal 3.

Prefer to fly direct from Houston Hobby Airport to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Houston Hobby to Chicago.
Find which airlines fly direct from Houston Hobby Airport to Chicago, which days they fly and book direct flights.

Direct departures

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

Direct returns

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

Reviews of the top 5 airlines serving from Hobby to Chicago

 
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 Chicago? 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 4244 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.1Boarding
8.6Crew
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

Plz don't take away free bags and free seating

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

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

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

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.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

I think the staff was nice. They took time to explain safety protocols. Boarding was great. They started early and our flight left a little early which was convenient. Having free games to play would have been better

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

Better than my las vagas experience, but still dissapointed with the airline support service.

As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

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

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

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