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$80 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 6/12. 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
Tue 7/2
Tue 7/9

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 41,909,192 times on KAYAK, and here is why:

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

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

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

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

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
9:35 am - 11:12 amHOU-MDW
25h 37m1 stop
10:26 pm - 9:04 amMDW-HOU
10h 38m1 stop
$170Frontier
Find Deal
Sat, Jun 15 - Sat, Jun 22
9:35 am - 11:12 amHOU-MDW
25h 37m1 stop
5:55 am - 9:52 pmMDW-HOU
15h 57m1 stop
$173Frontier
Find Deal
Sat, Jun 15 - Wed, Jun 19
9:35 am - 11:12 amHOU-MDW
25h 37m1 stop
6:00 am - 2:55 pmMDW-HOU
8h 55m1 stop
$174Frontier
Find Deal
Sat, Jun 15 - Tue, Jun 18
9:43 am - 9:45 pmHOU-MDW
12h 02m1 stop
5:40 am - 9:04 amMDW-HOU
27h 24m1 stop
$179Frontier
Find Deal
Thu, Jun 13 - Sat, Jun 15
9:35 am - 11:12 amHOU-MDW
25h 37m1 stop
8:53 pm - 6:28 pmMDW-HOU
21h 35m1 stop
$180Frontier
Find Deal
Sat, Jun 15 - Sun, Jun 23
9:35 am - 11:12 amHOU-MDW
25h 37m1 stop
6:00 am - 2:55 pmMDW-HOU
8h 55m1 stop
$186Frontier
Find Deal
Sat, Jun 15 - Tue, Jun 25
9:56 am - 10:00 pmHOU-MDW
12h 04m1 stop
6:00 am - 6:40 pmMDW-HOU
12h 40m1 stop
$190Frontier
Find Deal
Thu, Aug 8 - Tue, Aug 13
6:00 am - 11:44 amHOU-MDW
5h 44m1 stop
6:00 am - 12:10 pmMDW-HOU
6h 10m1 stop
$196Delta
Find Deal
Sat, Aug 17 - Tue, Aug 20
9:56 am - 10:00 pmHOU-MDW
12h 04m1 stop
10:55 pm - 9:32 pmMDW-HOU
22h 37m1 stop
$199Frontier
Find Deal
Thu, Aug 1 - Thu, Aug 8
6:00 am - 11:55 amHOU-MDW
5h 55m1 stop
6:00 am - 12:10 pmMDW-HOU
6h 10m1 stop
$334Delta
Find Deal
Tue, Jul 2 - Wed, Jul 10

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 Sunday and avoid Mondays if you are looking for the best rates. For your return to Houston Hobby Airport, you’ll find the best rates on Saturdays and the most expensive ones on Fridays.

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 June, where tickets cost $127 on average. On the other hand, the most expensive months are November and March, where the average cost of tickets is $575 and $376 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 ($170) and Delta ($196). Frontier proposed the cheapest one-way flight at $80.

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 8 nonstop flights that take off from Houston Hobby Airport and land in Chicago Midway Airport, with an average flight time of 2h 30m. The most common departure time is 6:00 pm and most flights take off in the morning. Each week, there are 43 flights. The most frequent day of departure is Monday, when 19% 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.

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 5:45 am and will be landing in Chicago Midway Airport at 8:10 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

January

High season

April

Cheapest flight

$80
Best time to beat the crowds with an average 43% drop in price.
Most popular time to fly and prices are also 42% 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 $80 for a one-way ticket and $170 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 $561 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 $149 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 5949 reviews
7.8Entertainment
7.3Food
8.7Crew
8.3Boarding
8.1Comfort
Airline reviews

Very helpful, convenient, nice crew members, no extra fees, helped us saving 4 hrs of travel by booking is on an earlier flight

10.0 ExcellentAntonia, May 2024HOU - VPS
Read more about Southwest reviews

Very helpful, convenient, nice crew members, no extra fees, helped us saving 4 hrs of travel by booking is on an earlier flight

Our first flight was so delayed that we had 10 mins to board the next one. We requested if the flight attendant could allow us off there plane first and they denied our request even though I have seen this done before. Luck was on our side that we didn’t miss our next flight.

Delay after delay after delay. Very disappointing I am about ready to give up on Southwest. One of the crewmembers sat and played games on her phone for the entire trip from Chicago to Baltimore. Unbelievable, very unprofessional, and very disappointing.

Not good.,At first delayed due to weather, then still had to load all the luggage, then a mechanical issue. Upon finally arriving, clothes wet as suitcases sat out in the rain. In a hard side suitcase! Ruined some paper items inside. Not happy!

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.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

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.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

Worst experience I have seen. The flight was cancelled without any reason.

Well I mean u get what u pay for so 🤷‍♂️

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

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.
6/12Wed
1 stopFrontier
12h 24mHOU-MDW
$80
6/8Sat
1 stopFrontier
11h 57mHOU-MDW
$81
9/17Tue
1 stopDelta
5h 24mHOU-MDW
$98
7/23Tue
1 stopFrontier
5h 35mHOU-MDW
$100
6/22Sat
1 stopFrontier
11h 55mHOU-MDW
$106
6/17Mon
1 stopFrontier
24h 19mHOU-MDW
$110
7/1Mon
1 stopFrontier
28h 20mHOU-MDW
$111
6/7Fri
1 stopAllegiant Air
5h 40mHOU-MDW
$133
6/9Sun
2 stops
25h 24mHOU-MDW
$217
10/18Fri
1 stopDelta
7h 29mHOU-MDW
$300

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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.
6/5Wed
multi-stopFrontier
19h 01mHOU-MDW
6/12Wed
multi-stopFrontier
26h 58mMDW-HOU
$229
6/3Mon
multi-stopFrontier
23h 18mHOU-MDW
6/8Sat
multi-stopFrontier
10h 38mMDW-HOU
$239
6/5Wed
multi-stopFrontier
19h 01mHOU-MDW
6/8Sat
multi-stopFrontier
27h 24mMDW-HOU
$243
6/7Fri
multi-stopFrontier
22h 57mHOU-MDW
6/13Thu
multi-stopFrontier
13h 16mMDW-HOU
$278
6/4Tue
multi-stopFrontier
13h 08mHOU-MDW
6/8Sat
multi-stopFrontier
10h 38mMDW-HOU
$289
6/4Tue
multi-stopFrontier
13h 08mHOU-MDW
6/8Sat
multi-stopFrontier
10h 38mMDW-HOU
$303
6/5Wed
multi-stopFrontier
19h 01mHOU-MDW
6/11Tue
multi-stopFrontier
8h 55mMDW-HOU
$308
6/4Tue
multi-stopFrontier
13h 08mHOU-MDW
6/6Thu
multi-stopFrontier
13h 16mMDW-HOU
$368
6/7Fri
multi-stopDelta
5h 55mHOU-MDW
6/10Mon
multi-stopDelta
5h 49mMDW-HOU
$558
6/3Mon
multi-stopDelta
5h 57mHOU-MDW
6/4Tue
multi-stopDelta
5h 42mMDW-HOU
$628

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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:

$750