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$70 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 5/29. 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
sex 6/21
sex 6/28

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 43,423,329 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.

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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
2:45 pm - 10:02 pmMDW-HOU
7h 17m1 stop
2:30 pm - 9:31 amHOU-MDW
19h 01m1 stop
$140Frontier
Find Deal
ter, jun 4 - qua, jun 5
10:01 pm - 9:34 pmMDW-HOU
23h 33m1 stop
2:30 pm - 9:31 amHOU-MDW
19h 01m1 stop
$142Frontier
Find Deal
sáb, jun 1 - qua, jun 5
2:45 pm - 10:02 pmMDW-HOU
7h 17m1 stop
2:30 pm - 9:31 amHOU-MDW
19h 01m1 stop
$144Frontier
Find Deal
ter, jun 4 - qua, jun 5
10:08 am - 6:55 pmMDW-HOU
8h 47m1 stop
10:44 pm - 11:08 amHOU-MDW
12h 24m1 stop
$148Frontier
Find Deal
sáb, jun 1 - qua, jun 12
2:45 pm - 10:02 pmMDW-HOU
7h 17m1 stop
2:30 pm - 9:31 amHOU-MDW
19h 01m1 stop
$150Frontier
Find Deal
ter, jun 4 - qua, jun 5
10:08 am - 6:55 pmMDW-HOU
8h 47m1 stop
10:24 pm - 11:09 amHOU-MDW
12h 45m1 stop
$155Frontier
Find Deal
sáb, jun 1 - dom, jun 2
5:55 am - 8:53 amMDW-HOU
26h 58m1 stop
9:33 am - 11:12 amHOU-MDW
25h 39m1 stop
$156Frontier
Find Deal
qua, jun 5 - sáb, jun 8
10:41 pm - 11:57 amMDW-HOU
13h 16m1 stop
9:33 am - 9:30 pmHOU-MDW
11h 57m1 stop
$172Frontier
Find Deal
qui, jun 6 - sáb, jun 8
6:00 am - 12:10 pmMDW-HOU
6h 10m1 stop
10:04 am - 2:57 pmHOU-MDW
4h 53m1 stop
$472Delta
Find Deal
ter, jul 23 - ter, jul 30
1:05 pm - 6:21 pmMDW-HOU
5h 16m1 stop
10:30 am - 5:14 pmHOU-MDW
6h 44m1 stop
$487Delta
Find Deal
sex, ago 30 - dom, set 1

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 Fridays.

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 January and March, where the average cost of tickets is $319 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 $70. KAYAK users also found Chicago Midway Airport to Houston Hobby Airport round-trip flights on Frontier from $140 and on Delta from $472.

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

Each day, there are between 6 and 11 nonstop flights that take off from Chicago Midway Airport and land in Houston Hobby Airport, with an average flight time of 2h 31m. The most common departure time is 7:00 pm and most flights take off in the morning. Each week, there are 63 flights. The most frequent day of departure is Thursday, when 17% of all weekly flights depart. The fewest flights depart on a Tuesday.

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.

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

$70
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 22% 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 $70 for a one-way ticket and $140 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 $388 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 $180 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 10585 reviews
8.6Crew
7.9Comfort
7.4Food
8.2Boarding
8.0Entertainment
Airline reviews

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

6.0 GoodPeter, May 2024SLC - HNL
Read more about Delta reviews

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 Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

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

Unfortunately not great, my flight was canceled with no notice given. I attempted to reach out to spirit airlines and have yet to receive any correspondence. I then had to book a new flight at two times the cost of the original.

They changed our gate 30 minutes before boarding began. We noticed about 20 people missed their flight due to doors closing early.

Flight was delayed 2+ hours missed a concert because of it…

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

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

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

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.
5/29qua
1 stopFrontier
8h 40mMDW-HOU
$70
6/4ter
1 stopFrontier
7h 17mMDW-HOU
$74
6/15sáb
1 stopFrontier
10h 38mMDW-HOU
$76
6/5qua
1 stopFrontier
26h 58mMDW-HOU
$80
6/8sáb
1 stopFrontier
27h 24mMDW-HOU
$84
5/30qui
1 stopFrontier
10h 28mMDW-HOU
$87
6/3seg
1 stopAllegiant Air
5h 16mMDW-HOU
$118
5/28ter
1 stopDelta
5h 40mMDW-HOU
$148
6/2dom
1 stopDelta
6h 22mMDW-HOU
$279
6/12qua
1 stopDelta
6h 14mMDW-HOU
$360

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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.
5/25sáb
multi-stopFrontier
23h 33mMDW-HOU
6/1sáb
multi-stopFrontier
11h 08mHOU-MDW
$140
5/25sáb
multi-stopFrontier
23h 33mMDW-HOU
5/28ter
multi-stopFrontier
12h 17mHOU-MDW
$143
5/26dom
multi-stopFrontier
16h 33mMDW-HOU
5/28ter
multi-stopFrontier
12h 17mHOU-MDW
$155
5/26dom
multi-stopFrontier
14h 52mMDW-HOU
6/2dom
multi-stopFrontier
12h 45mHOU-MDW
$213
5/25sáb
multi-stopFrontier
23h 33mMDW-HOU
6/2dom
multi-stopFrontier
12h 45mHOU-MDW
$216
5/25sáb
multi-stopFrontier
23h 33mMDW-HOU
5/30qui
multi-stopFrontier
13h 34mHOU-MDW
$222
5/25sáb
multi-stopFrontier
23h 33mMDW-HOU
5/28ter
multi-stopFrontier
12h 17mHOU-MDW
$236
5/26dom
multi-stopFrontier
16h 33mMDW-HOU
5/31sex
multi-stopFrontier
25h 33mHOU-MDW
$241
5/23qui
multi-stopDelta
6h 29mMDW-HOU
5/25sáb
multi-stopDelta
5h 57mHOU-MDW
$712
5/24sex
multi-stopDelta
6h 29mMDW-HOU
5/28ter
multi-stopDelta
5h 57mHOU-MDW
$767

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Chicago Midway Airport - Houston Hobby Airport Flights

Departure:

Chicago Midway Airport (undefined)United States

Destination:

Houston Hobby Airport (HOU)United States

Return flight deals:

Houston Hobby Airport - Chicago Midway Airport

Cabin classes:

$470