MDW

$53 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 3/20. 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 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
$84
Typical prices: $141-$224
Frontier
Fri 4/10Mon 4/13
IAH - MDW • Non-stop
Cheapest one-way
$53
Typical prices: $98-$169
Frontier
Fri 3/20
IAH - MDW • Non-stop
Our travelers' advice
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
Frontier
Cheapest • from $84 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
IAH
-
MDW
Cheapest • 38% average savings
HOU
-
MDW
Most popular
Insights
Insights
Insights
Insights
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 48% 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
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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

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
$84Frontier
Fri, Feb 20 - Sun, Feb 22
Frontier Logo
6:51 pm - 9:29 pm
IAH
-
MDW
2h 38mnonstop
Frontier Logo
3:00 pm - 6:06 pm
MDW
-
IAH
3h 06mnonstop
$87Frontier
Fri, Feb 20 - Mon, Feb 23
Frontier Logo
6:51 pm - 9:29 pm
IAH
-
MDW
2h 38mnonstop
Frontier Logo
6:45 am - 9:45 am
MDW
-
IAH
3h 00mnonstop
$88Frontier
Fri, Feb 20 - Sun, Feb 22
Frontier Logo
6:51 pm - 9:29 pm
IAH
-
MDW
2h 38mnonstop
Frontier Logo
3:00 pm - 6:06 pm
MDW
-
IAH
3h 06mnonstop
$95Frontier
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
$96Frontier
Fri, Mar 6 - Mon, Mar 23
Frontier Logo
1:43 pm - 4:13 pm
IAH
-
MDW
2h 30mnonstop
Frontier Logo
10:00 am - 12:58 pm
MDW
-
IAH
2h 58mnonstop
$97Frontier
Fri, Mar 13 - Mon, Mar 16
Frontier Logo
1:43 pm - 4:13 pm
IAH
-
MDW
2h 30mnonstop
Frontier Logo
10:00 am - 12:58 pm
MDW
-
IAH
2h 58mnonstop
$107Frontier
Wed, Feb 25 - Mon, Mar 2
Frontier Logo
7:59 pm - 2:26 pm
IAH
-
MDW
18h 27m
1 stop
Frontier Logo
6:45 am - 9:45 am
MDW
-
IAH
3h 00mnonstop
$108Frontier
Tue, Feb 24 - Tue, Mar 3
Southwest Logo
8:30 pm - 10:55 pm
HOU
-
MDW
2h 25mnonstop
Southwest Logo
7:55 pm - 10:40 pm
MDW
-
HOU
2h 45mnonstop
$157Southwest
Wed, Mar 4 - Sat, Mar 7
Southwest Logo
6:40 am - 9:05 am
HOU
-
MDW
2h 25mnonstop
Southwest Logo
9:40 pm - 12:25 am
MDW
-
HOU
2h 45mnonstop
$168Southwest
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.

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 $69 on the route between Houston George Bush Intcntl Airport (IAH) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 38% 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 Wednesdays 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 $182 (return) on average. On the other hand, the most expensive months are March and May, where the average cost of round-trip tickets is $320 and $298 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 48% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 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$53
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 $53 for a one-way ticket and $84 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

Frontier, Southwest

Frontier, 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

Frontier, Southwest

Frontier, 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 4268 reviews
7.5Entertainment
8.6Crew
7.0Food
8.0Comfort
8.1Boarding
Airline reviews

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

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

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.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

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

Information on your arrival and departure airports