MDW

$68 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 5/18. 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
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41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$145
Typical prices: $325-$222
Frontier
Wed 5/20Tue 5/26
IAH - MDW • 1 stop
Cheapest non-stop
$169
Typical prices: $367-$215
Southwest
Tue 6/2Wed 6/3
HOU - 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 $145 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 25m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 8% average savings
Most popular
Insights
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Insights
Insights
Avoid delays
Most punctual • 81% on-time
Best time • Fewest delays
Insights
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Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 52% compared to booking last minute.
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
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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, May 20 - Tue, May 26
Frontier Logo
5:45 am - 10:02 pm
IAH
-
MDW
16h 17m
1 stop
Frontier Logo
6:00 am - 7:34 am
MDW
-
IAH
25h 34m
1 stop
$145Frontier
Sat, Jun 6 - Tue, Jun 9
Frontier Logo
6:15 am - 10:02 pm
IAH
-
MDW
15h 47m
1 stop
Frontier Logo
6:00 am - 10:48 pm
MDW
-
IAH
16h 48m
1 stop
$149Frontier
Wed, May 13 - Tue, May 19
Frontier Logo
5:45 am - 11:09 am
IAH
-
MDW
5h 24m
1 stop
Frontier Logo
6:00 am - 2:58 pm
MDW
-
IAH
8h 58m
1 stop
$160Frontier
Tue, Jun 2 - Wed, Jun 3
Southwest Logo
8:40 pm - 11:05 pm
HOU
-
MDW
2h 25mnonstop
Southwest Logo
8:40 pm - 11:20 pm
MDW
-
HOU
2h 40mnonstop
$169Southwest
Wed, Jun 24 - Tue, Jun 30
Southwest Logo
9:25 pm - 11:50 pm
HOU
-
MDW
2h 25mnonstop
Southwest Logo
9:10 am - 1:50 pm
MDW
-
HOU
4h 40m
1 stop
$175Southwest
Wed, May 27 - Sat, May 30
Frontier Logo
5:45 am - 11:09 am
IAH
-
MDW
5h 24m
1 stop
Frontier Logo
11:59 am - 10:50 pm
MDW
-
IAH
10h 51m
1 stop
$180Frontier
Tue, Jun 2 - Thu, Jun 4
Southwest Logo
8:40 pm - 11:05 pm
HOU
-
MDW
2h 25mnonstop
Southwest Logo
9:40 pm - 12:10 am
MDW
-
HOU
2h 30mnonstop
$184Southwest
Wed, May 27 - Wed, Jun 3
Southwest Logo
8:40 pm - 11:05 pm
HOU
-
MDW
2h 25mnonstop
Southwest Logo
9:40 am - 2:00 pm
MDW
-
HOU
4h 20m
1 stop
$190Southwest
Wed, Jun 3 - Wed, Jun 10
Delta Logo
6:00 am - 11:56 am
HOU
-
MDW
5h 56m
1 stop
Delta Logo
6:00 am - 12:12 pm
MDW
-
HOU
6h 12m
1 stop
$197Delta
Tue, Jun 2 - Thu, Jun 4
Delta Logo
1:06 pm - 9:09 pm
HOU
-
MDW
8h 03m
1 stop
Delta Logo
6:23 am - 12:11 pm
MDW
-
HOU
5h 48m
1 stop
$208Delta
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 May.

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 absolute cheapest return flight from Houston to Chicago Midway Airport costs $197 on the route between Houston Hobby Airport (HOU) and Chicago Midway Airport (MDW). However, over the past month, flights between Houston George Bush Intcntl Airport (IAH) and Chicago Midway Airport (MDW) were, on average, 8% 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 July, where tickets cost $51 (return) on average. On the other hand, the most expensive months are January and December, where the average cost of round-trip tickets is $186 and $112 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 52% 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
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.

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.

Good to know

Cheapest flight$68
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 $68 for a one-way ticket and $145 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

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 Midway to Houston

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top 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 4314 reviews
8.6Crew
8.0Comfort
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

4.0 OkayCrystal, Apr 2026
MSY - MDW
Read more Southwest reviews

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

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

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

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

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

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

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

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

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

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

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

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

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

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

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

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

Information on your arrival and departure airports