HOU - MDW

$79 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 8/30. 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

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

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

Sat, Sep 6 - Sat, Sep 6
Southwest Logo
1:35 pm - 4:00 pmHOU-MDW
2h 25mnonstop
Southwest Logo
7:20 pm - 9:50 pmMDW-HOU
2h 30mnonstop
$157Southwest
Find Deal
Sat, Sep 6 - Mon, Sep 8
Southwest Logo
8:20 pm - 10:45 pmHOU-MDW
2h 25mnonstop
Southwest Logo
8:45 pm - 11:15 pmMDW-HOU
2h 30mnonstop
$177Southwest
Find Deal
Wed, Aug 27 - Wed, Sep 3
Southwest Logo
8:55 pm - 11:20 pmHOU-MDW
2h 25mnonstop
Southwest Logo
9:10 am - 11:45 amMDW-HOU
2h 35mnonstop
$187Southwest
Find Deal
Fri, Sep 5 - Mon, Sep 8
Southwest Logo
4:30 pm - 6:55 pmHOU-MDW
2h 25mnonstop
Southwest Logo
8:45 pm - 11:15 pmMDW-HOU
2h 30mnonstop
$197Southwest
Find Deal
Wed, Sep 3 - Sun, Sep 7
Southwest Logo
1:25 pm - 3:50 pmHOU-MDW
2h 25mnonstop
Southwest Logo
5:30 am - 11:00 amMDW-HOU
5h 30m1 stop
$198Southwest
Find Deal
Sat, Aug 23 - Mon, Aug 25
Southwest Logo
8:20 pm - 10:45 pmHOU-MDW
2h 25mnonstop
Southwest Logo
5:45 am - 8:15 amMDW-HOU
2h 30mnonstop
$207Southwest
Find Deal
Thu, Sep 4 - Sun, Sep 7
Southwest Logo
7:35 am - 10:05 amHOU-MDW
2h 30mnonstop
Southwest Logo
6:00 am - 8:30 amMDW-HOU
2h 30mnonstop
$208Southwest
Find Deal
Tue, Aug 26 - Thu, Aug 28
Southwest Logo
11:25 am - 1:55 pmHOU-MDW
2h 30mnonstop
Southwest Logo
3:30 pm - 7:45 pmMDW-HOU
4h 15m1 stop
$213Southwest
Find Deal
Sat, Aug 23 - Sat, Aug 30
Delta Logo
10:22 am - 3:28 pmHOU-MDW
5h 06m1 stop
Delta Logo
4:25 pm - 10:31 pmMDW-HOU
6h 06m1 stop
$217Delta
Find Deal
Wed, Aug 20 - Wed, Aug 27
Delta Logo
1:05 pm - 5:47 pmHOU-MDW
4h 42m1 stop
Delta Logo
6:00 am - 12:10 pmMDW-HOU
6h 10m1 stop
$237Delta
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 Saturday 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 August, where tickets cost $157 (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 51% 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$79
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 9% 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 $79 for a one-way ticket and $157 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.

  • 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 $179 or less one-way and $233 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 4246 reviews
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
8.1Boarding
Airline reviews

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.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

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

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.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

The ticketing agents were rude but then we had a great gate agent very nice we had to ride a buss out to where the plane was parked but it was in some back corner of the airport when we got to the plane the captain who was great btw was cleaning the plane because the same rude ticketing agent told them they we not contracted to vacuum the plane. The ride to las Vegas was fine We had a connecting flight to Dallas. The flight was fine but when we arrived in Dallas everyone who flew on any frontier airlines the picked up bags from baggage claim D15 had to wait over a hour for their bags to start we arrived at 11:30pm ish to the gate we didn't leave the baggage clamed till 12:50 am very not happy and i used to fly frontier 4 times a week for work in Denver i will not be using them again

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

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