MDW

$48 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 5/21. 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

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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Flights Deals
Expert advice
Useful Info
Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from Houston to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Houston to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
7:45 pm - 10:23 pmIAH-MDW
2h 38mnonstop
Frontier Logo
4:01 pm - 6:58 pmMDW-IAH
2h 57mnonstop
$121Frontier
Find Deal
Fri, Jul 18 - Mon, Jul 21
Frontier Logo
7:45 pm - 10:18 pmIAH-MDW
2h 33mnonstop
Frontier Logo
4:01 pm - 7:00 pmMDW-IAH
2h 59mnonstop
$122Frontier
Find Deal
Fri, Jun 6 - Fri, Jun 13
Frontier Logo
7:45 pm - 10:23 pmIAH-MDW
2h 38mnonstop
Frontier Logo
4:01 pm - 6:58 pmMDW-IAH
2h 57mnonstop
$124Frontier
Find Deal
Mon, Jul 21 - Fri, Jul 25
Frontier Logo
7:52 pm - 10:25 pmIAH-MDW
2h 33mnonstop
Frontier Logo
3:46 pm - 6:42 pmMDW-IAH
2h 56mnonstop
$125Frontier
Find Deal
Fri, May 30 - Mon, Jun 2
Southwest Logo
5:45 am - 8:10 amHOU-MDW
2h 25mnonstop
Southwest Logo
9:40 pm - 12:10 amMDW-HOU
2h 30mnonstop
$179Southwest
Find Deal
Wed, Jul 2 - Wed, Jul 2
Southwest Logo
8:40 pm - 11:10 pmHOU-MDW
2h 30mnonstop
Southwest Logo
5:50 am - 11:55 amMDW-HOU
6h 05m1 stop
$189Southwest
Find Deal
Wed, Jul 2 - Sat, Jul 5
Delta Logo
6:30 am - 1:06 pmIAH-MDW
6h 36m1 stop
Delta Logo
12:38 pm - 7:38 pmMDW-IAH
7h 00m1 stop
$217Delta
Find Deal
Wed, Jul 16 - Sat, Jul 19
Delta Logo
5:30 am - 12:28 pmIAH-MDW
6h 58m1 stop
Delta Logo
9:20 am - 5:56 pmMDW-IAH
8h 36m1 stop
$218Delta
Find Deal
Wed, May 21 - Sun, May 25
 Logo
5:26 am - 7:14 pmIAH-MDW
13h 48m2 stops
 Logo
8:04 pm - 12:07 amMDW-IAH
28h 03m2 stops
Fri, May 30 - Mon, Jun 2
 Logo
5:26 am - 7:14 pmIAH-MDW
13h 48m2 stops
 Logo
8:04 pm - 8:15 amMDW-IAH
36h 11m3 stops
Fri, May 30 - Mon, Jun 2
Expert advice

Expert advice for your flight from Houston to Midway

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Frontier

Frontier's Economy Bundle includes a carry-on bag and seat choice, offering budget-friendly convenience.


Frontier's Premium Bundle offers extra legroom and priority boarding, enhancing comfort for a small fee.

Read more about Frontierby Stefanie Waldek
Southwest

Southwest offers two free checked bags up to 50 pounds each, ideal for family travelers.


Southwest's free cancellation policy allows changes up to 10 minutes before departure, offering great flexibility.

Read more about Southwestby Blane Bachelor
Airports
IAH

IAH's security lines vary by terminal. Check wait times online and consider terminal-hopping only if the difference exceeds 20 minutes.

Read more about IAHby John Walton
MDW

Take the CTA Orange Line from MDW to downtown Chicago in 25-30 minutes. It's a convenient and traffic-free option.

Read more about MDWby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier and MDW

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
John Walton

John Walton

Expert on IAH

John Walton

John Walton

Independent aviation journalist John Walton took his first flight at eight weeks old and hasn’t stopped travelling since. A world-renowned expert in airlines and the passenger experience, he writes in depth on aviation, is a resident expert on travel in Japan and France, and offers a uniquely queer perspective on travelling the world.

Read more
Useful Info

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.

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

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Houston to Chicago Midway Airport.

Our data shows that the cheapest route for a return flight from Houston to Chicago Midway Airport cost $87 and was between Houston George Bush Intcntl Airport (IAH) and Chicago Midway Airport (MDW). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $87.

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 Tuesday and avoid Mondays if you are looking for the best rates. For your return to Houston, you’ll find the best rates on Tuesdays 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 August, where tickets cost $123 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $300 and $292 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. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Cheapest flight$48
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 $48 for a one-way ticket and $121 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?

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

Frontier, Southwest

Frontier, 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

Frontier, Southwest

Frontier, Southwest

Thursday

Southwest

Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

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 4294 reviews
8.0Comfort
7.1Food
8.6Crew
7.6Entertainment
8.2Boarding
Airline reviews

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

8.0 ExcellentJonathan, Apr 2025AUS - MSY
Read more Southwest reviews

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

Plz don't take away free bags and free seating

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

The last 30 min or so, they put the heat on full. We thought we were being basted.

I like that it was on time and the staff was friendly.

No space for our carryon and needed to check at plane before boarding !

Flight was ok. Boarding wasn’t fun. Flights were delayed by 12 minutes on each leg.

The plane wasn’t full, so we got the best seats

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.

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

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

Information on your arrival and departure airports

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