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Find cheap flights from Houston Hobby Airport to Chicago Midway Airport from $75

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 5/14. 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
0 bags
Mon 6/3
Mon 6/10

Search 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
In the last 7 days travelers have searched 43,693,958 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
7:46 pm - 6:54 amHOU-MDW
11h 08m1 stop
10:26 pm - 9:04 amMDW-HOU
10h 38m1 stop
$138Frontier
Find Deal
Sat, Jun 1 - Sat, Jun 8
10:52 pm - 11:09 amHOU-MDW
12h 17m1 stop
2:45 pm - 10:02 pmMDW-HOU
7h 17m1 stop
$140Frontier
Find Deal
Tue, May 28 - Tue, Jun 4
3:59 pm - 10:05 pmHOU-MDW
6h 06m1 stop
5:30 am - 3:52 pmMDW-HOU
10h 22m1 stop
$145Frontier
Find Deal
Tue, May 14 - Wed, May 15
3:59 pm - 10:05 pmHOU-MDW
6h 06m1 stop
5:30 am - 3:52 pmMDW-HOU
10h 22m1 stop
$146Frontier
Find Deal
Tue, May 14 - Wed, May 15
2:31 pm - 11:09 amHOU-MDW
20h 38m1 stop
10:01 pm - 9:34 pmMDW-HOU
23h 33m1 stop
$148Frontier
Find Deal
Wed, May 29 - Sat, Jun 1
3:59 pm - 10:05 pmHOU-MDW
6h 06m1 stop
10:22 pm - 8:50 amMDW-HOU
10h 28m1 stop
$151Frontier
Find Deal
Tue, May 14 - Thu, May 16
3:59 pm - 10:05 pmHOU-MDW
6h 06m1 stop
10:22 pm - 8:50 amMDW-HOU
10h 28m1 stop
$152Frontier
Find Deal
Tue, May 14 - Thu, May 16
3:59 pm - 10:05 pmHOU-MDW
6h 06m1 stop
5:30 am - 3:52 pmMDW-HOU
10h 22m1 stop
$159Frontier
Find Deal
Tue, May 14 - Wed, May 15
10:30 am - 5:59 pmHOU-MDW
7h 29m1 stop
1:05 pm - 6:21 pmMDW-HOU
5h 16m1 stop
$427Delta
Find Deal
Thu, Aug 8 - Tue, Aug 13
6:00 am - 11:55 amHOU-MDW
5h 55m1 stop
6:00 am - 12:14 pmMDW-HOU
6h 14m1 stop
$462Delta
Find Deal
Tue, Jul 2 - Tue, Jul 9

Flights from Hobby to Midway - Travel Insights & Trends

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 flights from Houston Hobby Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
When flying from Houston Hobby Airport to Chicago Midway Airport, you should consider leaving on a Saturday and avoid Fridays if you are looking for the best rates. For your return to Houston Hobby Airport, you’ll find the best rates on Tuesdays and the most expensive ones on Wednesdays.

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 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 March, where tickets cost $145 on average. On the other hand, the most expensive months are December and July, where the average cost of tickets is $378 and $364 respectively.

Which airlines provide the cheapest flights from Houston Hobby Airport to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Houston Hobby Airport to Chicago Midway Airport were found on Frontier ($138) and Delta ($427). Frontier proposed the cheapest one-way flight at $75.

Which airlines fly non-stop between Houston Hobby Airport and Chicago Midway Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Houston Hobby Airport to Chicago Midway Airport.
There is just one airline that flies from Houston Hobby Airport to Chicago Midway Airport direct and that is Southwest. The best one-way deal found from Southwest for the route is $291.

How many flights are there between Houston Hobby Airport and Chicago Midway Airport per day?

Each day, there are between 4 and 11 nonstop flights that take off from Houston Hobby Airport and land in Chicago Midway Airport, with an average flight time of 2h 29m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 45 flights. The most frequent day of departure is Tuesday, when 24% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Houston Hobby Airport and Chicago Midway Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Houston Hobby Airport to Chicago Midway Airport take?

Nonstop flights from Houston Hobby Airport generally make it to Chicago Midway Airport in 2h 25m. The flying distance between the two cities is 938 miles.

What’s the earliest departure time from Houston Hobby Airport to Chicago Midway Airport?

Early birds can take the earliest flight from Houston Hobby Airport at 5:05 am and will be landing in Chicago Midway Airport at 7:30 am.

What’s the latest departure time from Houston Hobby Airport to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from Houston Hobby Airport to Chicago Midway Airport jets off at 10:05 pm and lands at 12:30 am.

Good to know

Low season

February

High season

May

Cheapest flight

$75
Best time to beat the crowds with an average 39% drop in price.
Most popular time to fly with an average 30% increase in price.
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 $75 for a one-way ticket and $138 for a round-trip.

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

    No

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

    The Boeing 737-700 Passenger/BBJ1 (winglets) 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, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Houston to Chicago are Delta and Frontier. With an average price for the route of $578 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $183 and an overall rating of 6.2.

  • 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.

See more FAQs

Prefer to fly non-stop from Houston Hobby Airport to Chicago Midway Airport?

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

Nonstop 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

Nonstop 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
See more direct flights

Top 3 airlines serving 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.
8.1
SouthwestOverall score based on 6099 reviews
7.8Entertainment
8.3Boarding
7.3Food
8.7Crew
8.1Comfort
Airline reviews

The flight itself was good. We were delayed 1 1/2 hours which was not good.

10.0 ExcellentCindy, Mar 2024TPA - MDW
Read more about Southwest reviews

The flight itself was good. We were delayed 1 1/2 hours which was not good.

Flight was fine but new boarding policy was a drag Xtra time passenger group And Waiting until entire bridge empties before calling a list preferred... Waste of time

Wish that they would space out the boarding a little. COVID is still around and is real. No entertainment. Miss the peanuts.

Cramped older 737. Noisy passengers nearby. Wish you would change and make KC a hub with a direct from OKC. Best new airport!

A bit bumpy, but otherwise uneventful, and made up some delay in flight

Seats sook to be getting smaller on the planes. Still miss the peanuts on SW but the graham crackers and brickel are better than the mix.

Pros: "The ease of being able to switch my flight last minute"
Cons: "You could tell it was the end of the day for some employees"
Pros: "I like the boarding process. I like free checked bags."
Cons: "The wifi didn’t work. Not even able to watch a movie."
Cons: "Took an hour at Phoenix Sky Airport and 40 minutes at Midway Chicago to get luggage. Ridiculous Takes Southwest Air forever to deliver luggage"
Pros: "We landed safely and on time. That's all I expect, you did that well."

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

I didn’t like that I could not select my seat and was assigned a seat when I checked in at LAX

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

I paid for extra leg room. The flimsy plastic seat underneath the floatation seat did not line up with the arm rests. It seemed as if the plastic part was zip tied on but immovable. This caused severe uncomfortable for the duration of the flight.

Plane was clean but they do not allow bag drop until 1 hour before flight. Just encouraging late fees and other issues. The worst I have experienced. Total hostage situation, pay or you miss your flight.

Everything was good, and most importantly on time. They have been extremely tardy in some of my flights

I had to cancel within 1hour of the reservation an they put you through hell to . no live customer service desk. I'm handy caped and they make it almost impossible to cancel. They are steeling my money. You should not have that airline on your site. Contact me and I will give you all info. Of what the are doing to me just notable treatment they are set up like that to take people

Horrible flight, rude crew, someone had so mu h perfume on breathing was difficult.

I was singled out for being a Latina flying solo and the attendants took me out of line to put my luggage in the personal item bin to see if it would fly. Keep In mind I had just flown with the same luggage with no problem not even 5 days ago. The tag was sticking out a bit and the attendant was belligerent about charging me $100. I could not refuse because I didn’t wanna cause a scene. But today I felt targeted and embarrassed. I went online and found out that this happens a lot with this airline and to many minority women.

Book cheap flights from Houston to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Houston to Chicago found on KAYAK in the last 72 hours.
5/14Tue
1 stopFrontier
6h 06mHOU-MDW
$75
5/21Tue
1 stopFrontier
12h 17mHOU-MDW
$76
5/15Wed
1 stopFrontier
12h 26mHOU-MDW
$77
5/21Tue
1 stopFrontier
12h 17mHOU-MDW
$80
6/7Fri
1 stopAllegiant Air
5h 40mHOU-MDW
$120
5/31Fri
1 stopAllegiant Air
5h 27mHOU-MDW
$124
5/11Sat
1 stopDelta
4h 31mHOU-MDW
$154
6/30Sun
2 stops
25h 18mHOU-MDW
$242
6/30Sun
1 stopDelta
4h 38mHOU-MDW
$288
7/18Thu
3 stops
21h 47mHOU-MDW
$431

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Last minute flights from Hobby to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Houston to Chicago that are departing in the next 10 days.
5/7Tue
multi-stopFrontier
6h 06mHOU-MDW
5/11Sat
multi-stopFrontier
29h 00mMDW-HOU
$234
5/8Wed
multi-stopFrontier
21h 07mHOU-MDW
5/11Sat
multi-stopFrontier
18h 01mMDW-HOU
$235
5/7Tue
multi-stopFrontier
6h 06mHOU-MDW
5/13Mon
multi-stopFrontier
9h 44mMDW-HOU
$253
5/8Wed
multi-stopFrontier
21h 07mHOU-MDW
5/10Fri
multi-stopFrontier
9h 32mMDW-HOU
$268
5/7Tue
nonstopSouthwest
2h 25mHOU-MDW
5/9Thu
nonstopSouthwest
2h 40mMDW-HOU
$508
5/7Tue
multi-stopSouthwest
4h 10mHOU-MDW
5/9Thu
nonstopSouthwest
2h 40mMDW-HOU
$517
5/4Sat
multi-stopDelta
6h 37mHOU-MDW
5/7Tue
multi-stopDelta
6h 22mMDW-HOU
$518
5/7Tue
multi-stopSouthwest
6h 00mHOU-MDW
5/9Thu
nonstopSouthwest
2h 35mMDW-HOU
$522
5/4Sat
multi-stopDelta
6h 37mHOU-MDW
5/6Mon
multi-stopDelta
5h 40mMDW-HOU
$568
5/4Sat
multi-stopDelta
6h 37mHOU-MDW
5/6Mon
multi-stopDelta
9h 00mMDW-HOU
$942

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Houston Hobby Airport - Chicago Midway Airport Flights

Departure:

Houston Hobby Airport (HOU)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Houston Hobby Airport

Cabin classes:

$595