$44 Find Cheap Flights from Chicago Midway Airport to Houston

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 Houston departing on 2/20. 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 Houston

 
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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Everything you should know

Cheapest round-trip
$87
Overall average: $222
Frontier
Fri 2/20Sun 2/22
MDW - IAH • Non-stop
Cheapest one-way
$44
Typical prices: $69-$131
Frontier
Fri 2/20
MDW - IAH • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest offers two free checked bags for families.
Frontier's Economy Bundle includes a free carry-on.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Frontier
Cheapest • from $141 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
MDW-IAH
Cheapest • 29% average savings
MDW-IAH
Most popular
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 44% compared to booking last minute.
Insights
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Flight Deals

Cheap Flights from Midway to Houston (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 Houston 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 Midway to Houston

Fri, Feb 20 - Sun, Feb 22
Frontier Logo
3:00 pm - 6:06 pm
MDW
-
IAH
3h 06mnonstop
Frontier Logo
6:51 pm - 9:29 pm
IAH
-
MDW
2h 38mnonstop
$87Frontier
Fri, Feb 20 - Sun, Feb 22
Frontier Logo
3:00 pm - 6:06 pm
MDW
-
IAH
3h 06mnonstop
Frontier Logo
6:51 pm - 9:29 pm
IAH
-
MDW
2h 38mnonstop
$88Frontier
Sun, Feb 15 - Sun, Feb 22
Frontier Logo
3:00 pm - 6:06 pm
MDW
-
IAH
3h 06mnonstop
Frontier Logo
6:51 pm - 9:29 pm
IAH
-
MDW
2h 38mnonstop
$96Frontier
Wed, Feb 18 - Mon, Feb 23
Frontier Logo
6:00 am - 5:12 pm
MDW
-
IAH
11h 12m1 stop
Frontier Logo
10:30 am - 1:08 pm
IAH
-
MDW
2h 38mnonstop
$101Frontier
Wed, Feb 18 - Mon, Feb 23
Frontier Logo
6:00 am - 5:12 pm
MDW
-
IAH
11h 12m1 stop
Frontier Logo
10:30 am - 1:08 pm
IAH
-
MDW
2h 38mnonstop
$102Frontier
Fri, Feb 13 - Sun, Feb 22
Frontier Logo
3:00 pm - 6:06 pm
MDW
-
IAH
3h 06mnonstop
Frontier Logo
6:51 pm - 9:29 pm
IAH
-
MDW
2h 38mnonstop
$104Frontier
Sat, Feb 21 - Wed, Mar 4
Southwest Logo
5:00 am - 8:00 am
MDW
-
HOU
3h 00mnonstop
Southwest Logo
6:40 am - 9:05 am
HOU
-
MDW
2h 25mnonstop
$157Southwest
Wed, Jan 14 - Thu, Jan 15
Southwest Logo
3:30 pm - 6:20 pm
MDW
-
HOU
2h 50mnonstop
Southwest Logo
5:00 am - 7:25 am
HOU
-
MDW
2h 25mnonstop
$177Southwest
Sat, Feb 21 - Sun, Mar 1
Southwest Logo
5:50 pm - 8:40 pm
MDW
-
HOU
2h 50mnonstop
Southwest Logo
6:20 am - 8:40 am
HOU
-
MDW
2h 20mnonstop
$188Southwest
Thu, Feb 19 - Tue, Feb 24
Delta Logo
10:53 am - 4:28 pm
MDW
-
HOU
5h 35m1 stop
Delta Logo
5:25 am - 11:59 am
HOU
-
MDW
6h 34m1 stop
$207Delta
Booking Insights

KAYAK's insights & trends for Midway to Houston flights

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

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

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

The cheapest return flight from Chicago Midway Airport to Houston costs $97 on the route between Chicago Midway Airport (MDW) and Houston George Bush Intcntl Airport (IAH). Over the past month, this route was, on average, 29% cheaper than other Chicago Midway Airport-Houston routes. It is also the most popular route.

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

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

If your flying dates are flexible, you should consider flying to Houston on a Wednesday, 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. For your return ticket, we recommend flying on a Monday and avoiding Sundays for the best deals.

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

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, 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 is September, where tickets cost $125 (return) on average. On the other hand, the most expensive months are July and December, where the average cost of round-trip tickets is $335 and $330 respectively.

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

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, 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, you should book around 3 weeks before departure, which saves you about 44% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Expert advice

Expert advice for your flight from Midway to Houston

 
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.
Airlines
Frontier

Choose the Economy Bundle for a free carry-on and Standard seat selection.


Pay for bags early online to save money; airport fees are higher.

Southwest

Southwest offers free carry-on and personal item, but checked bags now incur fees.


Southwest's Rapid Rewards program offers unlimited rewards seats and no blackout dates.

Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier

Stefanie Waldek

Stefanie Waldek

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.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

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.

Read more

Good to know

Cheapest flight$44
Flight from Chicago Midway Airport to Houston George Bush Airport

When to book flights from Midway to Houston

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

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Houston was $44 for a one-way ticket and $87 for a round-trip.

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

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

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

    Chicago Midway Airport is served by only 1 airport and there are 2 airports in Houston. You will leave Chicago Midway Airport from Chicago Midway and you will be arriving in Houston at one of these airports: Houston Hobby or Houston George Bush Intcntl.

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

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

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

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

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

    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.

  • 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?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Houston 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?

    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 with an airline and back to Chicago Midway Airport with another airline.

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

    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 from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Prefer to fly direct from Chicago Midway Airport to Houston?

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

Direct departures

Chicago Midway to Houston

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Southwest

Southwest

Wednesday

Frontier, Southwest

Frontier, Southwest

Thursday

Southwest

Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Southwest

Southwest

Sunday

Southwest, Frontier

Southwest, Frontier

See more direct flights

Direct returns

Houston to Chicago Midway

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Southwest

Southwest

Wednesday

Frontier, Southwest

Frontier, Southwest

Thursday

Southwest

Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Southwest

Southwest

Sunday

Southwest, Frontier

Southwest, Frontier

See more direct flights

Reviews of the top 4 airlines serving from Midway to Houston

 
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 Houston? 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.
7.9
SouthwestOverall score based on 4250 reviews
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
Airline reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

10.0 ExcellentIlevba, Nov 2025
DCA - DAL
Read more Southwest reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Was good. I miss the free 2 checked bags. That was part of what made Southwest special

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

Cancelled my flight and the earliest that they are willing give me for the next flight which was 3 days later on a weekday. Only accommodation they are willing to give was $30 airline credit that will expire in 1 year

Flight was canceled, huge lines to get baggage returned. Most other airlines had delays but not widespread cancellations like Spirit.

My baby was crying uncontrollably for the longest time and the entire crew was SO supportive, I’m so appreciative of them. Thank you so much for the support during an exhausting moment. We got very lucky.

Uncomfortable seats and tiny tray table. Expensive snacks. Flight was on time and crew was pleasant but take me back to Southwest!

I didn't order food. I requested a Tomato juice and was given a boody mary mix. The serve needs to warn the customer what their given. It wasn't a huge deal, but I wasted $4.50.

EVERYTHING! It was so bad that I will be filing a claim for reimbursement for my seat as I could not fully sit in it due to an obese person being next to me and spilling over into my "space." And my personal item in the overhead been got crushed between two suitcases, so now my business laptop has been damaged beyond repair. Also, it was expensive! Since you pay for EVERYTHING, the cost of the trip was probably more than if you I used an airline that was not discounted. I will NEVER fly Spirit Airlines again!

One of worst experienc my family have every had with this airline. I was informed my Kayak that my flight was delayed and that my family will not make it to houston for our connecting flight. I contacted Spirit customer service to get my family on a later flight due to the delay in Vagas and them not making their connecting flight. The customer rep keep telling me that the flight from vagas is on time and not delayed. She even make to go to the spirit app on my phone and show me how to look up weather or not the flight was delayed. The app showed "on time" 20 minutes later when my family arrived at the airport for their flight, they were told that the flight was delayed and she will not make her connecting flight. I call spirit airline customer support again that night and spoke to another rep who apologize for his collegue and he told me that my family will receive a credit for this, this was on Saturday I still have not received the credit or an email letting me know when I will be credited for this inconvenience. This is not good business and it need to be fixed.

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

I wanted to upgrade my seat because I’m 6’2 and never have enough leg room for my comfort. They upgraded my seat for free putting me in an emergency exit seat. I was very comfortable

We had an almost 7 hour flight delay. We left the gate twice and taxi-ed and then returned the gate twice. Finally we got a new flight crew (our third one) and then left the gate to the final time before departing at 6:45pm (original flight time was 12pm). Out of Newark.

Not clean and was told I would get a great seat and it was not great at all

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

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

Information on your arrival and departure airports