$90 Find Cheap Flights from Chicago Midway Airport to Houston - Compare and Save

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 9/1. 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
$179
Typical prices: $264-$118
Southwest
Tue 9/22Wed 9/23
MDW - HOU • Non-stop
Cheapest non-stop
$198
Typical prices: $427-$259
Southwest
Sat 8/8Tue 8/11
MDW - HOU • Non-stop
Top airlines
Cheapest • from $179 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 36m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 9% average savings
Most popular
Insights
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Avoid delays
Most punctual • 80% on-time
Best time • Fewest delays
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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

Tue, Sep 22 - Wed, Sep 23
Southwest Logo
8:25 pm - 10:50 pm
MDW
-
HOU
2h 25mnonstop
Southwest Logo
4:45 pm - 7:10 pm
HOU
-
MDW
2h 25mnonstop
$179Southwest
Tue, Sep 22 - Wed, Sep 23
Southwest Logo
8:25 pm - 10:50 pm
MDW
-
HOU
2h 25mnonstop
Southwest Logo
5:55 pm - 9:50 pm
HOU
-
MDW
3h 55m
1 stop
$189Southwest
Tue, Sep 22 - Wed, Sep 23
Southwest Logo
7:40 am - 1:45 pm
MDW
-
HOU
6h 05m
2 stops
Southwest Logo
4:45 pm - 7:10 pm
HOU
-
MDW
2h 25mnonstop
$195Southwest
Sat, Aug 8 - Tue, Aug 11
Southwest Logo
1:45 pm - 4:15 pm
MDW
-
HOU
2h 30mnonstop
Southwest Logo
4:45 pm - 7:10 pm
HOU
-
MDW
2h 25mnonstop
$198Southwest
Wed, Aug 12 - Tue, Aug 18
Delta Logo
6:05 am - 11:15 am
MDW
-
IAH
5h 10m
1 stop
Delta Logo
4:37 pm - 10:36 pm
IAH
-
MDW
5h 59m
1 stop
$199Delta
Wed, Aug 12 - Tue, Aug 18
Delta Logo
5:10 pm - 10:05 pm
MDW
-
HOU
4h 55m
1 stop
Delta Logo
10:50 am - 4:15 pm
HOU
-
MDW
5h 25m
1 stop
$199Delta
Wed, Jul 15 - Tue, Jul 21
Frontier Logo
12:11 pm - 10:39 pm
MDW
-
IAH
10h 28m
1 stop
Frontier Logo
8:02 pm - 11:07 am
IAH
-
MDW
15h 05m
1 stop
$203Frontier
Tue, Oct 27 - Wed, Oct 28
Frontier Logo
7:25 am - 3:05 pm
MDW
-
IAH
7h 40m
1 stop
Frontier Logo
1:35 pm - 9:53 pm
IAH
-
MDW
8h 18m
1 stop
$210Frontier
Tue, Jul 28 - Tue, Aug 4
Delta Logo
9:19 am - 2:30 pm
MDW
-
IAH
5h 11m
1 stop
Delta Logo
5:41 am - 11:51 am
IAH
-
MDW
6h 10m
1 stop
$214Delta
Tue, Jul 28 - Tue, Aug 4
Frontier Logo
12:11 pm - 10:39 pm
MDW
-
IAH
10h 28m
1 stop
Frontier Logo
10:53 am - 10:03 pm
IAH
-
MDW
11h 10m
1 stop
$220Frontier
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.

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Houston departing in September.

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 absolute cheapest return flight from Chicago Midway Airport to Houston costs $234 on the route between Chicago Midway Airport (MDW) and Houston Hobby Airport (HOU). However, over the past month, flights between Chicago Midway Airport (MDW) and Houston George Bush Intcntl Airport (IAH) were, on average, 9% cheaper than other Chicago Midway Airport-Houston routes. The most popular route is between Chicago Midway Airport (MDW) and Houston Hobby Airport (HOU).

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 Friday, 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 Friday and avoiding Tuesdays 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 December, where tickets cost $50 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $187 and $151 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 15 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.
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$90
Flight from Chicago Midway Airport to Houston Hobby 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 5 days, the lowest price for a flight from Chicago Midway Airport to Houston 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?

    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

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 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

Reviews of the top 3 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 4237 reviews
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

The seat was not comfortable. 1D. My back was sore all night and the next day.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

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

The new seating arrangement is so over priced for what you get.

Snacks are always pretzels. Why can't you also offer peanuts ?

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

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.

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

Information on your arrival and departure airports