HOU - CHI

$62 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 3/19. 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

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Hobby to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
3:43 pm - 12:17 amHOU-MDW
8h 34m1 stop
6:40 am - 7:24 pmMDW-HOU
12h 44m1 stop
$130Frontier
Find Deal
Sat, Mar 1 - Sat, Mar 8
10:36 am - 12:17 amHOU-MDW
13h 41m1 stop
6:40 am - 7:24 pmMDW-HOU
12h 44m1 stop
$140Frontier
Find Deal
Wed, Mar 5 - Sat, Mar 8
10:36 am - 12:42 amHOU-ORD
14h 06m1 stop
6:45 am - 9:32 amORD-HOU
26h 47m1 stop
$140Frontier
Find Deal
Fri, Apr 11 - Sun, Apr 13
5:35 am - 7:55 amHOU-MDW
2h 20mnonstop
9:20 pm - 12:05 amMDW-HOU
2h 45mnonstop
$188Southwest
Find Deal
Fri, Mar 21 - Tue, Mar 25
5:35 am - 7:55 amHOU-MDW
2h 20mnonstop
10:45 pm - 1:30 amMDW-HOU
2h 45mnonstop
$197Southwest
Find Deal
Thu, Mar 6 - Mon, Mar 10
6:00 am - 11:59 amHOU-MDW
5h 59m1 stop
12:44 pm - 5:42 pmMDW-HOU
4h 58m1 stop
$237Delta
Find Deal
Tue, Feb 25 - Wed, Mar 5
6:03 am - 1:06 pmHOU-ORD
7h 03m1 stop
6:54 pm - 11:53 pmORD-HOU
4h 59m1 stop
$257American Airlines
Find Deal
Tue, Mar 18 - Tue, Mar 25
6:37 pm - 11:48 pmHOU-ORD
5h 11m1 stop
5:30 pm - 11:06 pmORD-HOU
5h 36m1 stop
$267Delta
Find Deal
Tue, Feb 25 - Tue, Mar 11
5:00 am - 9:34 amHOU-ORD
4h 34m1 stop
6:00 am - 1:52 pmORD-HOU
7h 52m1 stop
$300American Airlines
Find Deal
Sat, May 17 - Wed, May 21
11:20 am - 10:09 amHOU-MDW
22h 49m1 stop
10:54 am - 12:30 pmMDW-HOU
25h 36m1 stop
$331Allegiant Air
Find Deal
Thu, Mar 27 - Mon, Mar 31

Flights from Hobby to Chicago - Travel Insights & Trends

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 $148 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $225 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 season

January

High season

October

Cheapest flight

$62
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 8% 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 $62 for a one-way ticket and $130 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, Delta, JetBlue, 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 A320neo 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 $279 and an overall rating of 8.1, Southwest is the most popular choice. American Airlines is also a great choice for the route, with an average price of $243 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.

See more FAQs

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 $198 or less one-way and $274 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.
See more tips

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.
8.1
SouthwestOverall score based on 4482 reviews
8.2Boarding
8.7Crew
7.6Entertainment
7.1Food
8.1Comfort
Airline reviews

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.

10.0 ExcellentRachel, Jan 2025TPA - MDW
Read more Southwest reviews

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

The flight was semi-full with enough space to spread out. Wonderful, smooth, and quick flight.

We boarded the flight and set two and a half hours on the jetway. Would have been better if they had not boarded us at all. Plane was hot and it was limited ability to access the restrooms or get a drink of water. Very unpleasant experience

The flight was great. We were not offered any beverages though. And there was no real turbulence, so not sure why.

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

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

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.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.

The flight encountered a delay exceeding 4 hours. The food voucher issued was valued at $12, insufficient to cover our meal expenses. Consequently, I was unable to take my medication, leading to a drop in blood sugar levels and exacerbating my anxiety.

Airplane was cold. Flight attendants were rude. Phone charger did not work. No food available.

3hour delay In the last 3 months i had 3 flights and 2 of these had a more than 2:40 hrs delayed

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

I very late and supose be in home at 12 pm from yesterday but I stiill in detroi airport

I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in

Horrible. Take off was delayed by an hour. They were letting people board d the plane right before takeoff. I was delayed an hour when I arrived and late for my meeting. Spirit is NEVER on time.

Boarding attendant was rude. Crew on the plan were more interested in talking amongst themselves and did not ask parentage if they needed anything or even walk down the isles.

The flight landed with a delay and we had to wait almost an hour to be off boarded. So typical of spirit.

The gate employees and the flight crew were friendly and professional. Afterboarding we waited 20 minutes for another flight; a complimentary beverage would have ben appreciated for the inconvenience.

Everyone on the plane was wonderful. I can't say that the trip of flying was wonderful because I hadn't done that since I was 13 years old. Honestly I was terrified. What would make it better is if they didn't drive so fast but I know they have to. And if they could go up slowly and land slowly. But none of that they can control.

Horrible experience, they cancelled the flight , and we had to lose money on car rentals and hotels and tickets for extraction

Check in at Philadelphia international was absolutely terrible! I fly 2 to 3 times a month and avoid frontier at all cost and will never fly Frontier again! The night before travel, I tried checking in however, the app was giving me an error, so I went to the desktop, which instructed you that you need to use the app. The next day I presented at the check-in gate after trying at least a half dozen times prior to getting into the airport and continuing to getting the error in the app. I actually had rebooted my phone numerous times and reinstall the app just in case. My phone is only one generation older than the current model. It has no problems completing a frontier flight purchase or any other app issues. There was only three frontier employees working at check-in and a huge line while I was in line I continued to try and check in via the app. As I approach the desk, I was dreading dealing with the agent. He was extremely unprofessional, anti-semantic & very ignorant, and mean to the people in front of me, as well as the people who ended up being behind me. He literally told people “Man I don’t care bout y’all” in his native dialect! Maintaining my composure I approached and explained the situation. To which he replied, you’re gonna have to pay then! I don’t understand. It’s an issue with their app not allowing me to check in! Not my issue! He told me if I pay cash it would be $15, $25 if I pay credit card. I don’t understand a $10 difference for paying with a credit card? I am completely cashless so I continued to try using the app to avoid the $25 fee, Which I still don’t believe that I should be responsible for since it was Frontier’s technical issue!!! I continued to check in via the app a couple more times after he verified I was doing everything right he proceeded to continue to belittle the people behind me. Yelling at them saying I don’t care about you people! I cannot believe that this is the way that businesses would treat its customers! Unfortunately, the black mail with dreadlocks did not have a name tag all he had was a frontier sweater on! For the $25 fee that I ended up getting charged on my credit card. I should’ve just booked originally with Spirit or any other carrier! I have no problem paying fees that I should be responsible for, but when it’s due to a technical failure of a company, the customer should not be responsible for it! I cannot believe that it’s not frontier going out of business!

they delayed my flight which ended up, causing my layover flight to leave without me, resulting in me missing a flight and having to stay overnight in Houston international. I got no compensation other than a flight to my original location only a day later. i’ve never experienced such a unprofessional situation

Very easy with the app to board and staff skills

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

My experience with the phoenix airport was terrible, the personnel lay the ticket counter charged me for a carry on that fit in the carry on size box, and the two women I spoke with were terribly rude and not willing to help.,,, there was one lady “candy” on the flight crew that was amazing and is the only reason I stayed on the flight at all, because the other stewards helping people to get seated on the plane were terrible

I loked walking out on the tarmac to board and no first class. I didn't like that they have no snacks or onboard wifi to bide your time.

The plane was clean, the crew was friendly and helpful. It’s a low cost airline so there was no food, drinks or in flight entertainment but we didn’t expect any of these things. In the room for improvement department, they should install USB ports in seats to charge mobile devices.

The seats were extremely hard and uncomfortable, even for a budget airline.

The seats were extremely hard and uncomfortable. It was disappointing even for a budget airline.

Charging $74 for one checked bag is outrageous. I will never fly Frontier again.

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

Information on your arrival and departure airports

Compare transportation modes for Houston Hobby Airport to Chicago

Average priceAverage duration
Flights$2882h 20m
Buses$48020h 57m

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