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Find cheap flights from Chicago Midway Airport to Houston Hobby Airport from $59

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 5/18. 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 5/27
Mon 6/3

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 44,335,567 times on KAYAK, and here is why:

Save 22% 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
10:30 am - 3:30 pmMDW-HOU
29h 00m1 stop
2:31 pm - 5:12 pmHOU-MDW
26h 41m1 stop
$98Frontier
Find Deal
Sat, May 11 - Mon, May 20
10:01 pm - 9:34 pmMDW-HOU
23h 33m1 stop
2:31 pm - 5:12 pmHOU-MDW
26h 41m1 stop
$99Frontier
Find Deal
Sat, May 18 - Mon, May 20
10:30 am - 3:30 pmMDW-HOU
29h 00m1 stop
6:28 pm - 6:54 amHOU-MDW
12h 26m1 stop
$108Frontier
Find Deal
Sat, May 11 - Wed, May 15
6:31 pm - 7:13 pmMDW-HOU
24h 42m1 stop
3:59 pm - 10:05 pmHOU-MDW
6h 06m1 stop
$110Frontier
Find Deal
Sun, May 12 - Tue, May 14
9:45 pm - 12:15 amMDW-HOU
2h 30mnonstop
7:40 am - 6:25 pmHOU-MDW
10h 45m1 stop
$267Southwest
Find Deal
Mon, May 13 - Tue, May 14
8:45 am - 10:15 pmMDW-HOU
13h 30m2 stops
7:40 am - 6:25 pmHOU-MDW
10h 45m1 stop
$281Southwest
Find Deal
Mon, May 13 - Tue, May 14
9:45 pm - 12:15 amMDW-HOU
2h 30mnonstop
8:10 pm - 10:40 pmHOU-MDW
2h 30mnonstop
$282Southwest
Find Deal
Mon, May 13 - Tue, May 14
6:00 am - 12:22 pmMDW-HOU
6h 22m1 stop
4:04 pm - 10:01 pmHOU-MDW
5h 57m1 stop
$288Delta
Find Deal
Tue, May 7 - Sat, May 11
6:00 am - 12:10 pmMDW-HOU
6h 10m1 stop
4:04 pm - 10:01 pmHOU-MDW
5h 57m1 stop
$318Delta
Find Deal
Sat, May 4 - Sat, May 11
6:00 am - 12:10 pmMDW-HOU
6h 10m1 stop
4:04 pm - 10:01 pmHOU-MDW
5h 57m1 stop
$328Delta
Find Deal
Sat, May 4 - Tue, May 7

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 Tuesday and avoid Wednesdays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Saturdays 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 January, where tickets cost $191 on average. On the other hand, the most expensive months are June and March, where the average cost of tickets is $320 and $313 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 78 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 $59. KAYAK users also found Chicago Midway Airport to Houston Hobby Airport round-trip flights on Frontier from $98 and on Southwest from $267.

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

Each day, there are between 4 and 8 nonstop flights that take off from Chicago Midway Airport and land in Houston Hobby Airport, with an average flight time of 2h 37m. The most common departure time is 5:00 pm and most flights take off in the morning. Each week, there are 37 flights. The most frequent day of departure is Sunday, when 22% 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.

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 5:30 am and will be landing in Houston Hobby Airport at 8:00 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 9:45 pm and lands at 12:15 am.

Good to know

Low season

April

High season

November

Cheapest flight

$59
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 25% 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 $59 for a one-way ticket and $98 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 $394 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 $178 and an overall rating of 6.3.

  • 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 10966 reviews
8.2boarding
8.6crew
8.0entertainment
7.4food
7.9comfort
Airline reviews

Delta is one of the best airlines I have flown

10.0 ExcellentKellie, Apr 2024ANC - SEA
Read more about Delta reviews

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

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.

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…

I MISS MY FLY AND THEY NOT EVEN TRY TO GET ME ALEAST A CREDIT TO BUY ANOTHER TICKET BUT IS FINE I WOULD NEVER BUY A TICKET WITH SPIRIT EVER AGAIN

It’s a flying bus, no reclining seats, entertainment, charge ports. As if someone was out on limb to make my flight experience atrocious

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 was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

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.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

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.
5/18Sat
1 stopFrontier
23h 33mMDW-HOU
$59
9/4Wed
1 stopFrontier
7h 34mMDW-HOU
$75
5/29Wed
1 stopFrontier
8h 40mMDW-HOU
$80
5/8Wed
1 stopFrontier
10h 22mMDW-HOU
$86
5/5Sun
1 stopFrontier
24h 42mMDW-HOU
$90
5/26Sun
1 stopFrontier
16h 33mMDW-HOU
$91
8/17Sat
1 stopDelta
6h 07mMDW-HOU
$99
5/19Sun
1 stopFrontier
16h 33mMDW-HOU
$100
6/2Sun
1 stopFrontier
14h 52mMDW-HOU
$107
10/12Sat
1 stopDelta
6h 08mMDW-HOU
$193

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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.
5/1Wed
multi-stopFrontier
10h 22mMDW-HOU
5/3Fri
multi-stopFrontier
23h 24mHOU-MDW
$170
4/29Mon
multi-stopFrontier
9h 44mMDW-HOU
5/3Fri
multi-stopFrontier
23h 24mHOU-MDW
$208
4/28Sun
multi-stopFrontier
24h 46mMDW-HOU
5/3Fri
multi-stopFrontier
23h 24mHOU-MDW
$248
4/29Mon
multi-stopFrontier
9h 44mMDW-HOU
4/30Tue
multi-stopFrontier
6h 06mHOU-MDW
$258
4/29Mon
multi-stopFrontier
9h 44mMDW-HOU
5/1Wed
multi-stopFrontier
15h 52mHOU-MDW
$260
5/1Wed
multi-stopFrontier
10h 22mMDW-HOU
5/1Wed
multi-stopFrontier
21h 22mHOU-MDW
$261
4/28Sun
multi-stopFrontier
24h 46mMDW-HOU
4/30Tue
multi-stopFrontier
6h 06mHOU-MDW
$271
4/27Sat
multi-stopFrontier
29h 00mMDW-HOU
4/30Tue
multi-stopFrontier
19h 39mHOU-MDW
$290
4/30Tue
multi-stopDelta
5h 24mMDW-HOU
5/4Sat
multi-stopDelta
6h 37mHOU-MDW
$438
4/29Mon
multi-stopDelta
5h 39mMDW-HOU
5/4Sat
multi-stopDelta
6h 37mHOU-MDW
$488

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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