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$55 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 8/21. 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
Wed 7/10
Wed 7/17

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 42,898,604 times on KAYAK, and here is why:

Save 21% 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 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
10:26 pm - 9:04 amMDW-HOU
10h 38m1 stop
12:50 pm - 5:10 pmHOU-MDW
28h 20m1 stop
$121Frontier
Find Deal
Sat, Jun 22 - Mon, Jun 24
10:26 pm - 9:04 amMDW-HOU
10h 38m1 stop
12:50 pm - 5:10 pmHOU-MDW
28h 20m1 stop
$124Frontier
Find Deal
Sat, Jun 22 - Mon, Jun 24
9:45 pm - 9:49 pmMDW-HOU
24h 04m1 stop
3:15 pm - 8:50 pmHOU-MDW
5h 35m1 stop
$153Frontier
Find Deal
Tue, Jul 9 - Tue, Jul 16
10:55 pm - 9:32 pmMDW-HOU
22h 37m1 stop
12:32 pm - 5:10 pmHOU-MDW
28h 38m1 stop
$168Frontier
Find Deal
Thu, Aug 1 - Mon, Aug 5
12:06 pm - 6:28 pmMDW-HOU
6h 22m1 stop
3:46 pm - 12:00 pmHOU-MDW
20h 14m1 stop
$182Frontier
Find Deal
Mon, Jun 24 - Tue, Jun 25
6:00 am - 2:25 pmMDW-HOU
8h 25m1 stop
5:12 pm - 7:45 amHOU-MDW
14h 33m1 stop
$184Frontier
Find Deal
Tue, Jul 23 - Fri, Jul 26
10:26 pm - 9:04 amMDW-HOU
10h 38m1 stop
12:50 pm - 5:10 pmHOU-MDW
28h 20m1 stop
$188Frontier
Find Deal
Sat, Jun 22 - Mon, Jun 24
9:45 pm - 9:49 pmMDW-HOU
24h 04m1 stop
3:15 pm - 8:50 pmHOU-MDW
5h 35m1 stop
$191Frontier
Find Deal
Tue, Jul 9 - Tue, Jul 16
6:00 am - 12:10 pmMDW-HOU
6h 10m1 stop
10:04 am - 4:08 pmHOU-MDW
6h 04m1 stop
$314Delta
Find Deal
Sat, Aug 10 - Tue, Aug 27
10:28 am - 3:31 pmMDW-HOU
5h 03m1 stop
4:21 pm - 9:46 pmHOU-MDW
5h 25m1 stop
$432Delta
Find Deal
Sat, Jul 20 - Sat, Jul 27

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 $55. KAYAK users also found Chicago Midway Airport to Houston Hobby Airport round-trip flights on Frontier from $121 and on Delta from $314.

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

Each day, there are between 4 and 12 nonstop flights that take off from Chicago Midway Airport and land in Houston Hobby Airport, with an average flight time of 2h 30m. The most common departure time is 1:00 pm and most flights take off in the afternoon. Each week, there are 55 flights. The most frequent day of departure is Friday, 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 5:10 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

$55
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 $55 for a one-way ticket and $121 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 $387 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 $188 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 10295 reviews
8.0Entertainment
7.9Comfort
8.2Boarding
7.4Food
8.6Crew
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

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!

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

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

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.

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.
8/21Wed
1 stopFrontier
7h 34mMDW-HOU
$55
6/18Tue
1 stopFrontier
8h 55mMDW-HOU
$59
6/22Sat
1 stopFrontier
10h 38mMDW-HOU
$64
7/30Tue
1 stopFrontier
8h 25mMDW-HOU
$70
7/31Wed
1 stopFrontier
15h 34mMDW-HOU
$75
7/9Tue
1 stopFrontier
24h 04mMDW-HOU
$76
8/8Thu
1 stopFrontier
22h 37mMDW-HOU
$82
8/14Wed
1 stopFrontier
7h 34mMDW-HOU
$96
6/15Sat
1 stopDelta
6h 36mMDW-HOU
$325
7/3Wed
2 stopsDelta
8h 57mMDW-HOU
$451

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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.
6/13Thu
multi-stopFrontier
13h 16mMDW-HOU
6/14Fri
multi-stopFrontier
10h 47mHOU-MDW
$194
6/14Fri
multi-stopFrontier
26h 48mMDW-HOU
6/21Fri
multi-stopFrontier
10h 47mHOU-MDW
$236
6/13Thu
multi-stopFrontier
13h 16mMDW-HOU
6/16Sun
multi-stopFrontier
26h 04mHOU-MDW
$239
6/13Thu
multi-stopFrontier
13h 16mMDW-HOU
6/17Mon
multi-stopFrontier
28h 20mHOU-MDW
$240
6/13Thu
multi-stopFrontier
13h 16mMDW-HOU
6/15Sat
multi-stopFrontier
25h 37mHOU-MDW
$243
6/14Fri
multi-stopFrontier
26h 48mMDW-HOU
6/17Mon
multi-stopFrontier
28h 20mHOU-MDW
$248
6/14Fri
multi-stopFrontier
26h 48mMDW-HOU
6/18Tue
multi-stopFrontier
20h 14mHOU-MDW
$258
6/14Fri
multi-stopFrontier
26h 48mMDW-HOU
6/16Sun
multi-stopFrontier
26h 04mHOU-MDW
$262
6/15Sat
multi-stopDelta
6h 36mMDW-HOU
6/22Sat
multi-stopDelta
4h 49mHOU-MDW
$438
6/11Tue
multi-stopDelta
5h 22mMDW-HOU
6/16Sun
multi-stopDelta
5h 55mHOU-MDW
$601

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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