MDW - HOU

$103 Find Cheap Flights from Chicago Midway Airport to Houston Hobby Airport - 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 Hobby departing on 8/5. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$205
Typical prices: $202-$354
Southwest
Tue 8/18Sat 8/22
MDW - HOU • Non-stop
Cheapest one-way
$103
Typical prices: $108-$246
Southwest
Wed 8/5
MDW - HOU • Non-stop
Top airlines
Cheapest • from $205 (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 37m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Most punctual • 80% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
Cheapest • 47% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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

Tue, Aug 18 - Sat, Aug 22
Southwest Logo
8:25 pm - 10:50 pm
MDW
-
HOU
2h 25mnonstop
Southwest Logo
7:00 am - 9:25 am
HOU
-
MDW
2h 25mnonstop
$205Southwest
Sat, Aug 15 - Mon, Aug 17
Southwest Logo
7:20 am - 9:50 am
MDW
-
HOU
2h 30mnonstop
Southwest Logo
5:45 pm - 8:10 pm
HOU
-
MDW
2h 25mnonstop
$206Southwest
Tue, Jul 21 - Tue, Jul 28
Southwest Logo
5:50 pm - 8:25 pm
MDW
-
HOU
2h 35mnonstop
Southwest Logo
9:25 pm - 11:55 pm
HOU
-
MDW
2h 30mnonstop
$209Southwest
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
9:55 am - 1:50 pm
MDW
-
HOU
3h 55m
1 stop
Southwest Logo
3:50 pm - 6:15 pm
HOU
-
MDW
2h 25mnonstop
$211Southwest
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
7:50 am - 1:55 pm
MDW
-
HOU
6h 05m
1 stop
Southwest Logo
3:50 pm - 6:15 pm
HOU
-
MDW
2h 25mnonstop
$215Southwest
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
7:50 am - 1:55 pm
MDW
-
HOU
6h 05m
1 stop
Southwest Logo
3:50 pm - 6:15 pm
HOU
-
MDW
2h 25mnonstop
$216Southwest
Sat, Aug 15 - Mon, Aug 17
Southwest Logo
7:20 am - 9:50 am
MDW
-
HOU
2h 30mnonstop
Southwest Logo
5:45 pm - 8:10 pm
HOU
-
MDW
2h 25mnonstop
$217Southwest
Wed, Jul 15 - Sat, Jul 18
Southwest Logo
9:00 pm - 11:40 pm
MDW
-
HOU
2h 40mnonstop
Southwest Logo
5:45 pm - 11:15 pm
HOU
-
MDW
5h 30m
1 stop
$219Southwest
Tue, Jul 21 - Tue, Jul 28
Southwest Logo
3:10 pm - 8:40 pm
MDW
-
HOU
5h 30m
2 stops
Southwest Logo
6:20 pm - 8:45 pm
HOU
-
MDW
2h 25mnonstop
$220Southwest
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
9:55 am - 1:50 pm
MDW
-
HOU
3h 55m
1 stop
Southwest Logo
6:00 pm - 11:20 pm
HOU
-
MDW
5h 20m
1 stop
$221Southwest
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.

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

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 Hobby Airport departing in August.

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 Friday 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 $160 (return) on average. On the other hand, the most expensive months are June and March, where the average cost of round-trip tickets is $447 and $356 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$103
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 12% 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 5 days, the lowest price for a flight from Chicago Midway Airport to Houston Hobby Airport was $103 for a one-way ticket and $205 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 $337 and an overall rating of 7.9, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $199 and an overall rating of 5.6.

  • 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 $173 or less one-way and $343 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.
7.9
SouthwestOverall score based on 4246 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
7.0Food
8.6Crew
Airline reviews

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!

4.0 OkayAnonymous, May 2026
MSY - HOU
Read more Southwest reviews

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!

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

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

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.

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

First, my flight was a usual flight nothing exceptional or unexpected. Over all it was a normal, good flight! Second, your questionaire is wholly lacking in the proper options to which one can answer a question. Often on short flights, there is no food let alone entertainment so why isn't that reflected in your questionaire? A simple "not applicable" would cover that issue appropriately but no, your form arbitrarily enters an answer based on the initial assessment which normally isn't factual. Until you provide an accurate means of assessing flights, I'll no longer be completing of these unimpressive and misleading assessements. Thank you!

Easy to book and to get check in and get on and off.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

Chairs are not reclinable. Not ear phones for sale. Seats should be assigned to avoid confrontations. Flight attendants were AMAZING.

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.

My flight was canceled I was promised a reginf still not received.

The worst service , the agents from the counter are really bad . Poor customer service . They didnt help me to get in the flight . I was on line when they close the flight without telling and I couldn’t board the plane . I will like to get my money back ey back because it was their fault. Really bad management , bad manners, bad additud

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I fly Frontier often and generally don't have any issues. For some reason, the Denver to Houston's George Bush Intercontinental (IAH) flight always needs to wait on the tarmac in Houston because a gate is not available after landing. I've been stuck for as little as 15 minutes and as much as a little over an hour. I know only fly the Frontier Denver to IAH route when there is not an available flight to Houston Hobby (HOU).

Terrible Y lost my connection to Mexico, nobody of your company help me And y pay a lot of money for my baggage Until now I continue in the Houston airport I vneed you return my money

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

Everything was good, 20/30 minutes late waiting on a crew member. It’s hard to keep employees. Or serious employees I know. I remember one flight from Houston of Frontiers was almost 18 hours late. And another 4 hours late very poor. But I would rather be late and safe than the on the news. Thank you.

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

Information on your arrival and departure airports