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$76 Find cheap flights from Chicago Midway Airport to Houston Hobby 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 Midway to Hobby departing on 6/8. 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 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
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.

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
6:00 am - 1:34 pmMDW-HOU
7h 34m1 stop
7:30 pm - 11:52 amHOU-MDW
16h 22m1 stop
$138Frontier
Find Deal
Wed, Aug 28 - Tue, Sep 3
6:00 am - 1:34 pmMDW-HOU
7h 34m1 stop
5:24 pm - 11:52 amHOU-MDW
18h 28m1 stop
$169Frontier
Find Deal
Wed, Aug 28 - Mon, Sep 2
5:55 am - 9:52 pmMDW-HOU
15h 57m1 stop
9:56 am - 12:00 pmHOU-MDW
26h 04m1 stop
$173Frontier
Find Deal
Wed, Jun 12 - Sun, Jun 16
5:40 am - 9:04 amMDW-HOU
27h 24m1 stop
12:50 pm - 1:09 pmHOU-MDW
24h 19m1 stop
$174Frontier
Find Deal
Sat, Jun 15 - Mon, Jun 17
6:00 am - 6:31 pmMDW-HOU
12h 31m1 stop
7:30 pm - 11:52 amHOU-MDW
16h 22m1 stop
$188Frontier
Find Deal
Thu, Aug 29 - Tue, Sep 3
10:38 am - 6:10 pmMDW-HOU
7h 32m1 stop
10:30 am - 5:16 pmHOU-MDW
6h 46m1 stop
$227Delta
Find Deal
Tue, Oct 1 - Tue, Oct 29
10:11 am - 4:19 pmMDW-HOU
6h 08m1 stop
1:00 pm - 5:59 pmHOU-MDW
4h 59m1 stop
$257Delta
Find Deal
Sat, Nov 9 - Tue, Nov 12
7:50 pm - 10:20 pmMDW-HOU
2h 30mnonstop
3:45 pm - 10:00 pmHOU-MDW
6h 15m1 stop
$306Southwest
Find Deal
Mon, Jun 24 - Thu, Jun 27
10:55 pm - 1:20 amMDW-HOU
2h 25mnonstop
6:35 pm - 9:10 pmHOU-MDW
2h 35mnonstop
$312Southwest
Find Deal
Mon, Jun 24 - Thu, Jun 27
9:07 pm - 8:48 pmMDW-HOU
23h 41m3 stops
1:54 pm - 10:04 amHOU-MDW
20h 10m2 stops
Fri, Jul 12 - Sun, Jul 14

Flights from Midway to Hobby - Travel Insights & Trends

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.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Houston Hobby Airport?

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

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 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 April, where tickets cost $198 on average. On the other hand, the most expensive months are March and January, where the average cost of tickets is $323 and $319 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Houston Hobby Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
To get a below average price on the flight from Chicago Midway Airport to Houston Hobby Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 48 days before departure.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, Frontier offered the best one-way deal for that route, at $76. KAYAK users also found Chicago Midway Airport to Houston Hobby Airport round-trip flights on Frontier from $138 and on Delta from $227.

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

Each day, there are between 4 and 10 nonstop flights that take off from Chicago Midway Airport and land in Houston Hobby Airport, with an average flight time of 2h 29m. The most common departure time is 7:00 pm and most flights take off in the evening. Each week, there are 47 flights. The most frequent day of departure is Wednesday, when 21% of all weekly flights depart. The fewest flights depart on a Saturday.

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

The average nonstop flight takes 2h 25m, covering a distance of 938 miles.

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

Early birds can take the earliest flight from Chicago Midway Airport at 5:10 am and will be landing in Houston Hobby Airport at 7:40 am.

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

If you prefer to fly at night, the latest flight from Chicago Midway Airport to Houston Hobby Airport jets off at 10:55 pm and lands at 1:20 am.

Good to know

Low season

January

High season

May

Cheapest flight

$76
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 18% lower on average.
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 3 days, the lowest price for a flight from Chicago Midway Airport to Houston Hobby Airport was $76 for a one-way ticket and $138 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?

    Only American Airlines offers 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 Boeing 737-800 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, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to Houston are Delta and Frontier. With an average price for the route of $376 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 $182 and an overall rating of 6.2.

  • 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.

See more FAQs

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

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

Nonstop 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

Nonstop 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
See more direct flights

Top 3 airlines serving 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.
8.0
DeltaOverall score based on 10410 reviews
8.6Crew
7.9Comfort
8.2Boarding
7.4Food
8.0Entertainment
Airline reviews

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

10.0 ExcellentBarb, Jun 2024MSP - JFK
Read more about Delta reviews

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.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The plane was not on time for boarding or departure or arrivals.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

Seats suck, not enough room, overcrowded planes, hectic situation all together.

On time and fast. Overall it was a pleasant experience.

Delayed several times. Flight was to arrive at midnight and it arrive at 3 am. A 3 hour delay is already bad but one that has you arriving in the wee hour is just disruptive and overall unacceptable. The complete lack of restitution is a joke in keeping with Spirit’s reputation of ranking bottom-low in the pecking order.

Cancelled my flight , currently stuck in Houston and will likely miss my cruise

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

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.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

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

Book cheap flights from Chicago to Houston

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Houston found on KAYAK in the last 72 hours.
6/8Sat
1 stopFrontier
10h 38mMDW-HOU
$76
6/15Sat
1 stopFrontier
27h 24mMDW-HOU
$80
7/2Tue
1 stopFrontier
8h 55mMDW-HOU
$100
6/23Sun
1 stopFrontier
21h 35mMDW-HOU
$110
6/26Wed
1 stopFrontier
15h 57mMDW-HOU
$111
6/25Tue
1 stopFrontier
8h 55mMDW-HOU
$119
7/8Mon
1 stopFrontier
6h 22mMDW-HOU
$129
7/1Mon
1 stopFrontier
6h 22mMDW-HOU
$133
7/10Wed
1 stopDelta
6h 10mMDW-HOU
$159
6/16Sun
1 stopDelta
6h 14mMDW-HOU
$219

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Last minute flights from Midway to Hobby

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 Chicago to Houston that are departing in the next 10 days.
6/5Wed
multi-stopFrontier
26h 58mMDW-HOU
6/10Mon
multi-stopFrontier
24h 19mHOU-MDW
$150
6/3Mon
multi-stopFrontier
8h 40mMDW-HOU
6/8Sat
multi-stopFrontier
11h 57mHOU-MDW
$199
6/5Wed
multi-stopFrontier
15h 57mMDW-HOU
6/9Sun
multi-stopFrontier
26h 04mHOU-MDW
$209
6/5Wed
multi-stopFrontier
26h 58mMDW-HOU
6/9Sun
multi-stopFrontier
9h 15mHOU-MDW
$229
6/3Mon
multi-stopFrontier
8h 40mMDW-HOU
6/12Wed
multi-stopFrontier
12h 24mHOU-MDW
$239
6/3Mon
multi-stopFrontier
8h 40mMDW-HOU
6/13Thu
multi-stopFrontier
12h 02mHOU-MDW
$244
6/3Mon
multi-stopAllegiant Air
5h 16mMDW-HOU
6/7Fri
multi-stopAllegiant Air
5h 40mHOU-MDW
$388
6/6Thu
multi-stopDelta
6h 22mMDW-HOU
6/15Sat
multi-stopDelta
4h 49mHOU-MDW
$528
6/3Mon
multi-stopDelta
6h 36mMDW-HOU
6/5Wed
multi-stopDelta
5h 51mHOU-MDW
$628
6/5Wed
multi-stopDelta
5h 42mMDW-HOU
6/7Fri
multi-stopDelta
4h 53mHOU-MDW
$639

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Chicago Midway Airport - Houston Hobby Airport Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Houston Hobby Airport (HOU)United States

Return flight deals:

Houston Hobby Airport - Chicago Midway Airport

Cabin classes:

$470