HOU - CHI

$90 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 7/2. 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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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 Flight Deals 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.

Recent round-trip flight deals from Hobby to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Hobby to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
5:45 am - 8:10 amHOU-MDW
2h 25mnonstop
Southwest Logo
9:40 pm - 12:10 amMDW-HOU
2h 30mnonstop
$179Southwest
Find Deal
Wed, Jul 2 - Wed, Jul 2
Southwest Logo
8:40 pm - 11:10 pmHOU-MDW
2h 30mnonstop
Southwest Logo
5:50 am - 11:55 amMDW-HOU
6h 05m1 stop
$189Southwest
Find Deal
Wed, Jul 2 - Sat, Jul 5
Delta Logo
6:00 am - 12:31 pmHOU-ORD
6h 31m1 stop
Delta Logo
7:00 am - 12:01 pmORD-HOU
5h 01m1 stop
$217Delta
Find Deal
Sat, Jul 19 - Wed, Jul 30
Delta Logo
6:42 pm - 11:58 pmHOU-ORD
5h 16m1 stop
Delta Logo
9:45 am - 5:57 pmORD-HOU
8h 12m1 stop
$218Delta
Find Deal
Tue, May 20 - Sat, May 31
American Airlines Logo
6:31 pm - 11:56 pmHOU-ORD
5h 25m1 stop
American Airlines Logo
5:00 am - 9:43 amORD-HOU
4h 43m1 stop
$257American Airlines
Find Deal
Wed, Jun 4 - Sun, Jun 8
American Airlines Logo
5:00 am - 9:34 amHOU-ORD
4h 34m1 stop
American Airlines Logo
6:45 pm - 11:58 pmORD-HOU
5h 13m1 stop
$263American Airlines
Find Deal
Wed, May 21 - Wed, May 28
Sun Country Air Logo
6:30 pm - 5:15 pmHOU-ORD
22h 45m1 stop
Sun Country Air Logo
6:30 am - 5:42 pmORD-HOU
11h 12m1 stop
$265Sun Country Air
Find Deal
Thu, Jun 5 - Sun, Jun 8
Sun Country Air Logo
6:30 pm - 7:09 pmHOU-ORD
24h 39m1 stop
Sun Country Air Logo
6:17 pm - 5:30 pmORD-HOU
23h 13m1 stop
$275Sun Country Air
Find Deal
Sun, Jun 1 - Thu, Jun 19
 Logo
6:00 pm - 11:59 pmHOU-ORD
29h 59m2 stops
 Logo
6:45 am - 5:12 pmORD-HOU
10h 27m1 stop
Thu, Jul 3 - Sun, Jul 6
 Logo
6:00 pm - 11:59 pmHOU-ORD
29h 59m2 stops
 Logo
6:45 am - 5:12 pmORD-HOU
10h 27m1 stop
Thu, Jul 3 - Sun, Jul 6
Useful Info

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.

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

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

Our data shows that the cheapest route for a return flight from Houston Hobby Airport to Chicago cost $197 and was between Houston Hobby Airport (HOU) and Chicago Midway Airport (MDW). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $197.

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 Friday, 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 $149 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $214 and $203 respectively.

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 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 seasonOctober
Cheapest flight$90
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 9% 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 $90 for a one-way ticket and $179 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, Alaska Airlines, and Delta 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.

  • 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 $289 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 $245 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 $128 or less one-way and $237 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?

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
See more direct flights

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 4294 reviews
8.2Boarding
7.6Entertainment
8.6Crew
8.0Comfort
7.1Food
Airline reviews

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

8.0 ExcellentJonathan, Apr 2025AUS - MSY
Read more Southwest reviews

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.

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

The last 30 min or so, they put the heat on full. We thought we were being basted.

I like that it was on time and the staff was friendly.

No space for our carryon and needed to check at plane before boarding !

Flight was ok. Boarding wasn’t fun. Flights were delayed by 12 minutes on each leg.

The plane wasn’t full, so we got the best seats

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

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

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.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

The flight was on time. The seats are very narrow.

Seats are poor. They do not lean back. They do not even have pockets on the back, making it impossible to store a phone or a coke bottle. If you opt for basic economy cheap seats, they stick you always in the middle or window seat, even though there are unoccupied seats on the aisle. And then there is the nickel and diming. No carry-ons. And checking your carry-on is $70. At the end there is no price advantage but there is plenty of aggravation.

Worst Airplane ride I ever have taken... My purchased seat was changed without my consent

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

They changed our departure time 6 times before I even reached the airport. Delayed, Ontime, Delayed Back on time, Then Delayed. We finally boarded the plane and then we had to sit on the runway for over an hour only to be told they were taking us back to the gate for an additional 2 hour delay. Lack of communication and a complete waste of time! Never again!

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

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

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

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Compare transportation modes for Houston Hobby Airport to Chicago

Average priceAverage duration
Flights$2422h 25m
Buses$33628h 10m

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