MDW - HOU

$99 Find Cheap Flights from Chicago Midway Airport to Houston Hobby 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 Midway to Hobby departing on 4/28. 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 Hobby Airport

 
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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$197
Overall average: $276
Southwest
Sat 4/18Sat 4/25
MDW - HOU • Non-stop
Cheapest one-way
$99
Typical prices: $104-$191
Southwest
Tue 4/28
MDW - HOU • Non-stop
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 44m
Direct flights
Direct flights
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Direct flights
Direct flights
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Avoid delays
Most punctual • 81% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 29% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 53% price drop
Most popular
Good to know
Good to know
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Good to know
Good to know
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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 Hobby!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Hobby (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 Hobby 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 Hobby

Sat, Apr 18 - Sat, Apr 25
Southwest Logo
6:05 pm - 8:50 pm
MDW
-
HOU
2h 45mnonstop
Southwest Logo
3:25 pm - 5:50 pm
HOU
-
MDW
2h 25mnonstop
$197Southwest
Sat, Apr 18 - Sat, Apr 25
Southwest Logo
12:55 pm - 5:15 pm
MDW
-
HOU
4h 20m
1 stop
Southwest Logo
3:25 pm - 5:50 pm
HOU
-
MDW
2h 25mnonstop
$203Southwest
Sat, May 16 - Wed, May 20
Southwest Logo
6:05 pm - 8:50 pm
MDW
-
HOU
2h 45mnonstop
Southwest Logo
11:10 am - 3:40 pm
HOU
-
MDW
4h 30m
1 stop
$207Southwest
Sat, Apr 18 - Sat, Apr 25
Southwest Logo
10:00 am - 1:55 pm
MDW
-
HOU
3h 55m
1 stop
Southwest Logo
8:10 am - 12:10 pm
HOU
-
MDW
4h 00m
1 stop
$208Southwest
Wed, Apr 29 - Wed, May 6
Southwest Logo
9:40 am - 2:00 pm
MDW
-
HOU
4h 20m
1 stop
Southwest Logo
7:35 am - 11:35 am
HOU
-
MDW
4h 00m
1 stop
$212Southwest
Sat, Apr 18 - Sat, Apr 25
Southwest Logo
12:55 pm - 5:15 pm
MDW
-
HOU
4h 20m
1 stop
Southwest Logo
10:50 am - 4:50 pm
HOU
-
MDW
6h 00m
2 stops
$213Southwest
Fri, Apr 17 - Tue, Apr 21
Southwest Logo
9:40 pm - 12:20 am
MDW
-
HOU
2h 40mnonstop
Southwest Logo
6:10 pm - 8:35 pm
HOU
-
MDW
2h 25mnonstop
$217Southwest
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
9:40 am - 2:00 pm
MDW
-
HOU
4h 20m
1 stop
Southwest Logo
2:40 pm - 8:20 pm
HOU
-
MDW
5h 40m
2 stops
$218Southwest
Wed, Apr 29 - Wed, May 6
Southwest Logo
8:00 am - 1:55 pm
MDW
-
HOU
5h 55m
2 stops
Southwest Logo
2:40 pm - 7:35 pm
HOU
-
MDW
4h 55m
1 stop
$222Southwest
Sat, Apr 18 - Sat, Apr 25
Southwest Logo
10:30 am - 5:00 pm
MDW
-
HOU
6h 30m
2 stops
Southwest Logo
10:50 am - 4:50 pm
HOU
-
MDW
6h 00m
2 stops
$223Southwest
Booking Insights

KAYAK's insights & trends for Midway to Hobby flights

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

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

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

If your flying dates are flexible, you should consider flying to Houston Hobby Airport 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 Hobby Airport. 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 Hobby Airport?

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 Hobby 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 Chicago Midway Airport to Houston Hobby Airport is September, where tickets cost $125 (return) on average. On the other hand, the most expensive months are July and February, where the average cost of round-trip tickets is $335 and $328 respectively.

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

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 Hobby 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 Chicago Midway Airport to Houston Hobby Airport, you should book around 3 weeks before departure, which saves you about 29% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$99
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Chicago Midway Airport to Houston Hobby Airport

When to book flights from Midway to Hobby

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

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Houston Hobby Airport was $99 for a one-way ticket and $197 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

    Chicago Midway Airport and Houston Hobby Airport are both served by 1 main airport. You will leave Chicago Midway Airport from Chicago Midway and will be arriving at Houston Hobby.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Houston Hobby Airport?

    American Airlines, and JetBlue offer inflight Wi-Fi service on the Chicago Midway Airport to Houston Hobby Airport flight route.

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

    The Airbus A321neo is the aircraft model that flies most regularly on the Chicago Midway Airport to Houston Hobby Airport flight route.

  • On which days can I fly direct from Chicago Midway Airport to Houston Hobby Airport?

    There are nonstop flights from Chicago Midway Airport to Houston Hobby Airport on a daily basis.

  • Which is the best airline for flights from Chicago to Houston, Southwest or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to Houston are Southwest and Frontier. With an average price for the route of $333 and an overall rating of 8.0, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $202 and an overall rating of 5.7.

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

  • 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 Hobby Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Houston Hobby Airport 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 Hobby 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 Houston Hobby Airport with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and HOU can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Houston Hobby 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 Houston Hobby Airport from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Houston Hobby Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $214 or less one-way and $335 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Houston Hobby Airport?

 
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 Hobby.
Find which airlines fly direct from Chicago Midway Airport to Houston Hobby Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Houston Hobby

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 Hobby 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 airlines flying from Midway to Hobby

 
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 Hobby? 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 4320 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

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

6.0 GoodChris, Mar 2026
DAL - SAT
Read more Southwest reviews

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 ?

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

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

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.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

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

Information on your arrival and departure airports