MDW - HOU

$90 Find Cheap Flights from Chicago Midway Airport to Houston Hobby Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Hobby departing on 5/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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KAYAK searches hundreds of travel sites at once for deals on flights to Houston Hobby Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Houston, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Houston, as well as popular online travel agencies
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Flights Deals

Cheap Flight Deals from Midway to Hobby (MDW-HOU)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Hobby that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Midway to Hobby

KAYAK's recommended round-trip deals from the most popular airlines that fly from Midway to Hobby.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
9:40 pm - 12:10 amMDW-HOU
2h 30mnonstop
Southwest Logo
1:35 pm - 4:05 pmHOU-MDW
2h 30mnonstop
$179Southwest
Find Deal
Tue, Jul 1 - Fri, Jul 4
Southwest Logo
9:55 am - 3:40 pmMDW-HOU
5h 45m1 stop
Southwest Logo
1:35 pm - 4:05 pmHOU-MDW
2h 30mnonstop
$189Southwest
Find Deal
Tue, Jul 1 - Fri, Jul 4
Southwest Logo
1:25 pm - 4:05 pmMDW-HOU
2h 40mnonstop
Southwest Logo
5:45 am - 8:10 amHOU-MDW
2h 25mnonstop
$197Southwest
Find Deal
Wed, Jun 4 - Wed, Jun 18
Southwest Logo
8:45 am - 11:30 amMDW-HOU
2h 45mnonstop
Southwest Logo
9:00 pm - 11:30 pmHOU-MDW
2h 30mnonstop
$198Southwest
Find Deal
Wed, May 21 - Sat, May 24
Southwest Logo
5:30 am - 10:10 amMDW-HOU
4h 40m1 stop
Southwest Logo
9:00 pm - 11:30 pmHOU-MDW
2h 30mnonstop
$199Southwest
Find Deal
Wed, May 21 - Sat, May 24
Southwest Logo
10:00 am - 2:15 pmMDW-HOU
4h 15m1 stop
Southwest Logo
8:40 pm - 11:10 pmHOU-MDW
2h 30mnonstop
$203Southwest
Find Deal
Wed, Jun 4 - Wed, Jun 18
Southwest Logo
6:30 am - 9:10 amMDW-HOU
2h 40mnonstop
Southwest Logo
8:40 pm - 11:10 pmHOU-MDW
2h 30mnonstop
$205Southwest
Find Deal
Tue, May 27 - Tue, Jul 29
Southwest Logo
8:30 pm - 11:15 pmMDW-HOU
2h 45mnonstop
Southwest Logo
5:25 am - 10:40 amHOU-MDW
5h 15m1 stop
$206Southwest
Find Deal
Sat, May 24 - Tue, May 27
Delta Logo
4:25 pm - 9:35 pmMDW-HOU
5h 10m1 stop
Delta Logo
1:00 pm - 5:58 pmHOU-MDW
4h 58m1 stop
$309Delta
Find Deal
Sat, Sep 6 - Sat, Sep 13
Delta Logo
6:00 am - 12:05 pmMDW-HOU
6h 05m1 stop
Delta Logo
6:00 am - 11:55 amHOU-MDW
5h 55m1 stop
$315Delta
Find Deal
Mon, Aug 18 - Fri, Aug 22
Useful Info

KAYAK's insights & trends for Midway to Hobby flights

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

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

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

If your flying dates are flexible, you should consider flying to Houston Hobby Airport on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago Midway Airport to Houston Hobby Airport. For your return ticket, we recommend flying on a Tuesday and avoiding Mondays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Houston Hobby Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Houston Hobby Airport is July, where tickets cost $159 (return) on average. On the other hand, the most expensive months are November and March, where the average cost of round-trip tickets is $288 and $286 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Houston Hobby Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to Houston Hobby Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low seasonAugust
High seasonNovember
Cheapest flight$90
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly with an average 26% increase in price.
Flight from Chicago Midway Airport to Houston Hobby Airport

When to book flights from Midway to Hobby

Are your dates flexible? Find out the best times to travel from Midway to Hobby based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Houston Hobby Airport flights

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Houston Hobby Airport was $90 for a one-way ticket and $179 for a round-trip.

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

    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 Chicago Midway Airport to Houston Hobby Airport?

    Chicago Midway Airport and Houston Hobby Airport are both served by 1 main airport. You will leave Chicago Midway Airport from Chicago Midway and will be arriving at Houston Hobby.

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

    Only American Airlines offers inflight Wi-Fi service on the Chicago Midway Airport to Houston Hobby Airport flight route.

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

    The Airbus A321neo is the aircraft model that flies most regularly on the Chicago Midway Airport to Houston Hobby Airport flight route.

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

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Houston are Southwest and Delta. With an average price for the route of $324 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $387 and an overall rating of 8.0.

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

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Houston Hobby Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Houston Hobby Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Houston Hobby Airport from Chicago Midway 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 Chicago Midway Airport to Houston Hobby Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Houston Hobby Airport with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and HOU can sometimes prove cheaper using this method.

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

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Houston Hobby Airport from Chicago Midway 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 Chicago Midway Airport to Houston Hobby Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $118 or less one-way and $263 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Houston Hobby Airport?

Find which airlines fly direct from Chicago Midway Airport to Houston Hobby Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Houston Hobby

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Houston Hobby to Chicago Midway

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 4 airlines serving from Midway to Hobby

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Houston. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Hobby? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4294 reviews
7.6Entertainment
7.1Food
8.6Crew
8.0Comfort
8.2Boarding
Airline reviews

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

10.0 ExcellentReginald, Mar 2025MDW - LGA
Read more Southwest reviews

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

First, my flight was a usual flight nothing exceptional or unexpected. Over all it was a normal, good flight! Second, your questionaire is wholly lacking in the proper options to which one can answer a question. Often on short flights, there is no food let alone entertainment so why isn't that reflected in your questionaire? A simple "not applicable" would cover that issue appropriately but no, your form arbitrarily enters an answer based on the initial assessment which normally isn't factual. Until you provide an accurate means of assessing flights, I'll no longer be completing of these unimpressive and misleading assessements. Thank you!

Easy to book and to get check in and get on and off.

Excellent experience. WiFi worked on this leg of My trip

First time I’ve ever missed a flight and it was an international flight.. Southwest put me on the next flight and it was the best experience possible.

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

WiFi could have been a little more consistent - otherwise a phenomenal and positive experience. The 1000 mile giveaway was awesome!!!

Your employees need to learn how to talk to people as creations of Yah. We are not their children nor are we lower than them.

Helpful attendants at check-in is very good. The $70 charge for a checked bags I didn't care for.and the constant charges for picking a seat and faster check-in are too much. Please cut the prices by at least 50% would be fantastic!

The flight was delayed over an hour and we had to sit on the plane. Crew does not apologize due to the delay. Spirit will NEVER do anything to give a customer a better experience. A child next to me was kicking me the whole time. I don't ever enjoy flying with Spirit.

Flight was ok with exception of the multiple delays. As with all Spirit flights, the sights are extremely uncomfortable and lack leg space. However, the price savings is the plus.

Easy! As long as you don’t mind no frills, our flight was enjoyable and on time

Okay for the most part but Good boarding and on time

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

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