HOU - CHI

$85 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 6/30. 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

 
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
$169
Typical prices: $347-$217
Southwest
Tue 5/5Tue 5/19
HOU - MDW • Non-stop
Cheapest one-way
$85
Typical prices: $82-$179
Southwest
Tue 6/30
HOU - MDW • Non-stop
Top airlines
Cheapest • from $169 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 25m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 82% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 29% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 21% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals
Booking Insights
Flight Deals

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

Tue, May 5 - Tue, May 19
Southwest Logo
7:10 am - 9:35 am
HOU
-
MDW
2h 25mnonstop
Southwest Logo
12:15 pm - 2:55 pm
MDW
-
HOU
2h 40mnonstop
$169Southwest
Tue, May 5 - Tue, May 12
Southwest Logo
1:55 pm - 4:20 pm
HOU
-
MDW
2h 25mnonstop
Southwest Logo
9:40 am - 2:00 pm
MDW
-
HOU
4h 20m
1 stop
$175Southwest
Wed, May 13 - Wed, May 20
Southwest Logo
6:10 pm - 8:35 pm
HOU
-
MDW
2h 25mnonstop
Southwest Logo
5:30 am - 10:50 am
MDW
-
HOU
5h 20m
1 stop
$179Southwest
Wed, Apr 29 - Thu, Apr 30
Southwest Logo
8:40 pm - 11:05 pm
HOU
-
MDW
2h 25mnonstop
Southwest Logo
9:40 pm - 12:20 am
MDW
-
HOU
2h 40mnonstop
$184Southwest
Wed, May 13 - Wed, May 20
Southwest Logo
4:55 pm - 10:15 pm
HOU
-
MDW
5h 20m
1 stop
Southwest Logo
5:30 am - 10:50 am
MDW
-
HOU
5h 20m
1 stop
$189Southwest
Tue, Apr 28 - Wed, Apr 29
Southwest Logo
1:10 pm - 10:55 pm
HOU
-
ORD
9h 45m
1 stop
Southwest Logo
11:55 am - 5:50 pm
ORD
-
HOU
5h 55m
1 stop
$189Southwest
Wed, Apr 29 - Thu, Apr 30
Southwest Logo
8:40 pm - 11:05 pm
HOU
-
MDW
2h 25mnonstop
Southwest Logo
10:00 am - 2:00 pm
MDW
-
HOU
4h 00m
1 stop
$190Southwest
Wed, Jun 3 - Thu, Jun 4
Southwest Logo
2:50 pm - 7:30 pm
HOU
-
MDW
4h 40m
1 stop
Southwest Logo
9:40 pm - 12:10 am
MDW
-
HOU
2h 30mnonstop
$194Southwest
Tue, May 12 - Wed, May 13
Delta Logo
6:00 am - 11:56 am
HOU
-
MDW
5h 56m
1 stop
Delta Logo
5:10 pm - 10:26 pm
MDW
-
HOU
5h 16m
1 stop
$197Delta
Wed, May 6 - Wed, May 13
Delta Logo
10:53 am - 6:47 pm
HOU
-
ORD
7h 54m
1 stop
Delta Logo
9:49 am - 4:09 pm
ORD
-
HOU
6h 20m
1 stop
$197Delta
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.

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Houston Hobby Airport to Chicago departing in May.

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 $197 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 Monday. On your return trip to Houston Hobby Airport, you should consider flying back on a Thursday, and avoid Mondays 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 January, where tickets cost $166 (return) on average. On the other hand, the most expensive months are March and July, where the average cost of round-trip tickets is $272 and $248 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 $357, 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 29% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$85
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 18% increase in price.
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 $85 for a one-way ticket and $169 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 Airbus A321neo is the aircraft model that flies most regularly on the Houston Hobby Airport to Chicago flight route.

  • Which airline alliances offer flights from Houston Hobby Airport to Chicago?

    Star Alliance, and oneworld are the airline alliances operating flights between Houston Hobby Airport and Chicago, with Star Alliance being the most commonly used for this 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 United Airlines?

    The two airlines most popular with KAYAK users for flights from Houston to Chicago are Southwest and United Airlines. With an average price for the route of $286 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 $292 and an overall rating of 7.4.

  • 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 $208 or less one-way and $277 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 4334 reviews
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
Airline reviews

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

6.0 GoodKenley, Apr 2026
AUS - LAS
Read more Southwest reviews

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I elected to pay for the upgrades and found very little difference

WiFi was not working and didn’t have a beverage service

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

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

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

I had a terrible experience. My flight got delayed from Atlanta to Chicago on Monday April 6, 2026, and that led to me missing my next flight to Brussels. United Airlines didn’t provide me with any accommodation for shelter. I had to sleep at the airport in Chicago. The next flight I was put on didn’t leave until the evening hours of Tuesday 4/7/2026.

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Flights were on time. Free Wifi on plane. Everything was well organized.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

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

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

Forced to check bags. Crew uninterested in collecting trash. Unclean seats.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

My first time experience with Spirit Air was not good at all.The reason i did not know to cancel 24Hrs before flight depature you do charge cancellation fee. It's ridiculous policy.Actually you should provide full voucher instead of charging cancellation fee. Confirmation Code# ZNVPHG Thanks Much , Rita S

That this is my second time the they cancel flights and they always wait until the last minute to let people know

Spirit is awful. Do not fly spirit. Nothing but delays, cancellations.

Nothing. We didn’t even have a pilot until one hour after our flight was set to depart and now we are waiting for a gate on a very hot packed aircraft. Spirit has lost its goddamn minds and we will never fly again. On the way down the delay went from 5 minutes to 6 hours to cancelled.

Delayed 11 hours with two being on our destinations tarmac, no compensation or refund and was told I would actually get charged a $200 cancellation fee if I decided to switch airlines for my return flight. For their inconvenience they gave a $10 meal voucher to split between two people in a airport.

Like Spirit but bad that you have to pay for water 🙃

If there are delays, it takes less than a minute for a Spirit employee to make an announcement. It’s very simple.

For a change, friendly staff at check-in and in flight.

Delayed both in takeoff and landing, trash plane no amenities, I've said it before but I'll never fly Spirit again.

It’s was a cheap flight and they got us there safely. It’s just their whole business model that make the experience “meh.” They make you paranoid about whether your personal item is too big. They make you paranoid about being crammed into a middle seat at the back of the plane. They purposely cram people together leaving multiple rows completely empty and even after the door closes the FA’s announce that everyone has to sit in their assigned seat. We knew what we were buying and in that regard we got a cheap and safe flight but it felt like they do their best to take any enjoyment out of the experience. That’s all on management, not the crew.

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Everything you need to know for your flight from Hobby to Chicago

Information on your arrival and departure airports