HOU - MDW

$59 Find Cheap Flights from Houston Hobby Airport 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 Hobby to Midway departing on 1/14. 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
$117
Overall average: $237
Southwest
Tue 1/6Fri 1/9
HOU - MDW • Non-stop
Cheapest non-stop
$117
Typical prices: $143-$257
Southwest
Tue 1/6Thu 1/8
HOU - MDW • Non-stop
Top airlines
Southwest
Cheapest • from $117 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 45% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 24% price drop
July
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 Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Hobby to Midway (HOU-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hobby 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 Hobby to Midway

Tue, Jan 6 - Fri, Jan 9
Southwest Logo
8:30 pm - 10:55 pmHOU-MDW
2h 25mnonstop
Southwest Logo
7:55 pm - 10:40 pmMDW-HOU
2h 45mnonstop
$117Southwest
Find Deal
Wed, Dec 31 - Tue, Jan 6
Southwest Logo
6:35 am - 9:00 amHOU-MDW
2h 25mnonstop
Southwest Logo
6:15 am - 9:15 amMDW-HOU
3h 00mnonstop
$152Southwest
Find Deal
Wed, Dec 3 - Wed, Dec 3
Southwest Logo
6:35 am - 9:00 amHOU-MDW
2h 25mnonstop
Southwest Logo
5:15 pm - 8:00 pmMDW-HOU
2h 45mnonstop
$157Southwest
Find Deal
Tue, Dec 9 - Fri, Dec 12
Southwest Logo
2:35 pm - 5:00 pmHOU-MDW
2h 25mnonstop
Southwest Logo
9:55 pm - 12:35 amMDW-HOU
2h 40mnonstop
$177Southwest
Find Deal
Thu, Jan 15 - Sun, Jan 18
Southwest Logo
6:30 am - 8:50 amHOU-MDW
2h 20mnonstop
Southwest Logo
7:55 pm - 10:40 pmMDW-HOU
2h 45mnonstop
$183Southwest
Find Deal
Thu, Jan 1 - Tue, Jan 6
Southwest Logo
6:35 am - 9:00 amHOU-MDW
2h 25mnonstop
Southwest Logo
3:30 pm - 6:20 pmMDW-HOU
2h 50mnonstop
$185Southwest
Find Deal
Wed, Dec 3 - Wed, Dec 3
Southwest Logo
3:00 pm - 7:20 pmHOU-MDW
4h 20m1 stop
Southwest Logo
8:35 pm - 11:20 pmMDW-HOU
2h 45mnonstop
$187Southwest
Find Deal
Tue, Jan 6 - Fri, Jan 9
Southwest Logo
12:50 pm - 6:05 pmHOU-MDW
5h 15m1 stop
Southwest Logo
7:55 pm - 10:40 pmMDW-HOU
2h 45mnonstop
$193Southwest
Find Deal
Fri, Dec 5 - Sun, Dec 7
Delta Logo
6:47 pm - 11:47 pmHOU-MDW
5h 00m1 stop
Delta Logo
5:13 pm - 10:48 pmMDW-HOU
5h 35m1 stop
$217Delta
Find Deal
Wed, Nov 12 - Wed, Nov 19
Delta Logo
6:48 pm - 11:40 pmHOU-MDW
4h 52m1 stop
Delta Logo
6:00 am - 1:28 pmMDW-HOU
7h 28m1 stop
$234Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Hobby to Midway flights

Get data-powered insights and trends into flights from Hobby to Midway 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 Houston Hobby Airport to Chicago Midway Airport?

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

Your flight ticket price will generally be cheaper if you fly to Chicago Midway Airport on a Monday and more expensive on a Sunday. On your return trip to Houston Hobby Airport, you should consider flying back on a Wednesday, and avoid Sundays for better deals.

What is the cheapest month to fly from Houston Hobby Airport 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 Hobby Airport 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 Hobby Airport to Chicago Midway Airport is September, where tickets cost $182 (return) on average. On the other hand, the most expensive months are May and March, where the average cost of round-trip tickets is $298 and $292 respectively.

How far in advance should I book a flight from Houston Hobby Airport 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 Hobby Airport 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 Hobby Airport to Chicago Midway Airport, you should book around 2 weeks before departure, which saves you about 45% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$59
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Houston Hobby Airport to Chicago Midway Airport

When to book flights from Hobby to Midway

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

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

    In the last 3 days, the lowest price for a flight from Houston Hobby Airport to Chicago Midway Airport was $59 for a one-way ticket and $117 for a round-trip.

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

    No

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

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

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

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Houston Hobby Airport to Chicago Midway Airport flight route.

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

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

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

    The two airlines most popular with KAYAK users for flights from Houston to Chicago are Southwest and Frontier. With an average price for the route of $281 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 $182 and an overall rating of 5.8.

  • How does KAYAK find such low prices on flights from Houston Hobby Airport 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 Hobby Airport 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 Hobby Airport 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 Hobby 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 Houston Hobby Airport 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 Hobby Airport with another airline. Booking your flights between Houston Hobby Airport and MDW 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 Houston Hobby Airport 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 Hobby 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 Houston Hobby Airport to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $138 or less one-way and $217 or less round-trip.

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

Direct departures

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

Direct returns

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

Reviews of the top airlines flying from Hobby 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 Hobby 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 4242 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
Airline reviews

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.

2.0 MediocreThomas, Oct 2025SAT - STL
Read more Southwest reviews

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

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

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

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

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

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