MDW

$70 Find Cheap Flights from Houston to Chicago Midway 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 Houston to Midway departing on 5/12. 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 Midway Airport

 
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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$149
Overall average: $221
Multiple Airlines
Wed 4/15Tue 4/21
IAH - MDW • 1 stop
Cheapest non-stop
$161
Typical prices: $136-$269
Frontier
Fri 4/10Mon 4/13
IAH - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest's two free checked bags suit family travelers.
Frontier's Economy Bundle includes a carry-on and seat choice.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $140 (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 and Frontier. Average duration is 2h 23m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 57% average savings
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 83% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 54% compared to booking last minute.
Insights
Insights
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Houston to Midway

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

Wed, Apr 15 - Tue, Apr 21
Multiple Airlines Logo
12:35 pm - 7:31 pm
IAH
-
MDW
6h 56m
1 stop
Multiple Airlines Logo
2:15 pm - 10:50 pm
MDW
-
IAH
8h 35m
1 stop
$149Multiple Airlines
Wed, May 6 - Wed, May 13
Frontier Logo
5:45 am - 10:02 pm
IAH
-
MDW
16h 17m
1 stop
Frontier Logo
6:00 am - 2:58 pm
MDW
-
IAH
8h 58m
1 stop
$151Frontier
Wed, Apr 15 - Tue, Apr 28
Multiple Airlines Logo
12:35 pm - 7:31 pm
IAH
-
MDW
6h 56m
1 stop
Multiple Airlines Logo
2:15 pm - 10:50 pm
MDW
-
IAH
8h 35m
1 stop
$153Multiple Airlines
Sat, May 2 - Tue, May 5
Multiple Airlines Logo
12:35 pm - 6:37 pm
IAH
-
MDW
6h 02m
1 stop
Multiple Airlines Logo
6:00 am - 2:58 pm
MDW
-
IAH
8h 58m
1 stop
$155Multiple Airlines
Wed, May 6 - Tue, May 12
Frontier Logo
5:45 am - 10:02 pm
IAH
-
MDW
16h 17m
1 stop
Frontier Logo
6:00 am - 2:58 pm
MDW
-
IAH
8h 58m
1 stop
$157Frontier
Thu, Apr 16 - Tue, Apr 21
Frontier Logo
7:55 pm - 7:59 am
IAH
-
MDW
12h 04m
1 stop
Frontier Logo
2:15 pm - 10:50 pm
MDW
-
IAH
8h 35m
1 stop
$159Frontier
Fri, Apr 10 - Mon, Apr 13
Frontier Logo
1:27 pm - 3:59 pm
IAH
-
MDW
2h 32mnonstop
Frontier Logo
9:20 am - 12:32 pm
MDW
-
IAH
3h 12mnonstop
$161Frontier
Wed, Apr 15 - Tue, Apr 21
Southwest Logo
7:10 am - 9:35 am
HOU
-
MDW
2h 25mnonstop
Southwest Logo
12:15 pm - 2:55 pm
MDW
-
HOU
2h 40mnonstop
$197Southwest
Wed, Apr 15 - Tue, Apr 21
Southwest Logo
7:10 am - 9:35 am
HOU
-
MDW
2h 25mnonstop
Southwest Logo
9:40 am - 2:00 pm
MDW
-
HOU
4h 20m
1 stop
$203Southwest
Sat, May 2 - Wed, May 6
Southwest Logo
8:10 am - 12:10 pm
HOU
-
MDW
4h 00m
1 stop
Southwest Logo
9:40 am - 2:00 pm
MDW
-
HOU
4h 20m
1 stop
$208Southwest
Booking Insights

KAYAK's insights & trends for Houston to Midway flights

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

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

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 to Chicago Midway Airport departing in April.

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

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

The cheapest return flight from Houston to Chicago Midway Airport costs $49 on the route between Houston George Bush Intcntl Airport (IAH) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 57% cheaper than other Houston-Chicago Midway Airport routes. The most popular route is between Houston Hobby Airport (HOU) and Chicago Midway Airport (MDW).

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

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

When flying from Houston to Chicago Midway Airport, you should consider leaving on a Monday and avoid Sundays if you are looking for the best rates. For your return to Houston, you’ll find the best rates on Fridays and the most expensive ones on Sundays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Houston to Chicago Midway 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 Houston to Chicago Midway Airport is September, where tickets cost $185 (return) on average. On the other hand, the most expensive months are January and March, where the average cost of round-trip tickets is $559 and $354 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Houston to Chicago Midway 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 Houston to Chicago Midway Airport, you should book around 2 weeks before departure, which saves you about 54% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Expert advice

Expert advice for your flight from Houston to Midway

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Good to know

Cheapest flight$65
Flight from Houston George Bush Airport to Chicago Midway Airport

When to book flights from Houston to Midway

Are your dates flexible? Find out the best times to travel from Houston to Midway 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 to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from Houston to Chicago Midway Airport was $70 for a one-way ticket and $140 for a round-trip.

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

    Yes, you'll most likely have to show a valid passport before boarding the plane in Houston and on arrival in Chicago Midway Airport.

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

    On your way to Chicago Midway Airport, you’ll fly out from one of these Houston airports: Houston Hobby or Houston George Bush Intcntl. You’ll be landing at Chicago Midway.

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

    We unfortunately don’t have that data for this specific route.

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

    SkyTeam is the only airline alliance operating flights between Houston and Chicago Midway Airport.

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Houston 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 to Chicago Midway 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 Chicago Midway Airport with an airline and back to Houston with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Houston to Chicago Midway 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 Chicago Midway Airport from Houston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Prefer to fly direct from Houston to Chicago Midway Airport?

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

Direct departures

Houston to Chicago Midway

Monday

Frontier,Southwest

Frontier,Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Frontier,Southwest

Frontier,Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Houston

Monday

Frontier,Southwest

Frontier,Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Frontier,Southwest

Frontier,Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top 3 airlines serving from Houston to Midway

 
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 Houston to Midway? 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 4318 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

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

6.0 GoodChris, Mar 2026
DAL - SAT
Read more Southwest reviews

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!

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Great vacation. Can't wait till next year for another one.

The seats were comfortable, and the boarding process was pretty smooth.

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Extremely disappointed with Delta. They canceled flight last minute and then I rebooked the other flights and with which were delayed as well

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.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Everything you need to know for your flight from Houston to Midway

Information on your arrival and departure airports