Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

HOU - MDW

Find cheap flights from Houston Hobby Airport to Chicago Midway Airport from $73

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 5/14. 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
Fri 6/7
Fri 6/14

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 43,968,530 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
10:52 pm - 12:00 pmHOU-MDW
13h 08m1 stop
6:00 am - 2:55 pmMDW-HOU
8h 55m1 stop
$140Frontier
Find Deal
Tue, Jun 4 - Tue, Jun 11
10:24 pm - 11:19 amHOU-MDW
12h 55m1 stop
2:45 pm - 10:02 pmMDW-HOU
7h 17m1 stop
$141Frontier
Find Deal
Sun, May 19 - Tue, May 21
10:52 pm - 11:09 amHOU-MDW
12h 17m1 stop
10:08 am - 6:55 pmMDW-HOU
8h 47m1 stop
$142Frontier
Find Deal
Tue, May 28 - Sat, Jun 1
9:33 am - 9:30 pmHOU-MDW
11h 57m1 stop
5:55 am - 9:52 pmMDW-HOU
15h 57m1 stop
$144Frontier
Find Deal
Sat, Jun 8 - Wed, Jun 12
9:33 am - 11:12 amHOU-MDW
25h 39m1 stop
5:55 am - 8:53 amMDW-HOU
26h 58m1 stop
$150Frontier
Find Deal
Sat, Jun 8 - Wed, Jun 12
2:31 pm - 11:09 amHOU-MDW
20h 38m1 stop
10:22 pm - 8:50 amMDW-HOU
10h 28m1 stop
$152Frontier
Find Deal
Wed, May 29 - Thu, May 30
2:16 pm - 7:43 pmHOU-MDW
5h 27m1 stop
2:22 pm - 7:38 pmMDW-HOU
5h 16m1 stop
$267Allegiant Air
Find Deal
Fri, May 31 - Mon, Jun 3
10:30 am - 5:14 pmHOU-MDW
6h 44m1 stop
6:00 am - 12:04 pmMDW-HOU
6h 04m1 stop
$296Delta
Find Deal
Sat, Aug 31 - Sun, Sep 1
8:20 am - 11:00 amHOU-MDW
2h 40mnonstop
3:00 pm - 8:20 pmMDW-HOU
5h 20m1 stop
$402Southwest
Find Deal
Thu, May 23 - Tue, May 28
4:04 pm - 10:01 pmHOU-MDW
5h 57m1 stop
6:00 am - 12:22 pmMDW-HOU
6h 22m1 stop
$418Delta
Find Deal
Sat, Jun 1 - Wed, Jun 5

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 Saturday and avoid Sundays if you are looking for the best rates. For your return to Houston Hobby Airport, you’ll find the best rates on Tuesdays 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 $133 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.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure 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 average of all the values for each month.
To get a below average price on the flight from Houston Hobby Airport to Chicago Midway Airport, you should book around 3 days before departure. For the absolute cheapest price, our data suggests you should book 19 days before departure.

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 ($140) and Allegiant Air ($267). Frontier proposed the cheapest one-way flight at $73.

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 6 and 11 nonstop flights that take off from Houston Hobby Airport and land in Chicago Midway 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 morning. Each week, there are 69 flights. The most frequent day of departure is Monday, when 16% of all weekly flights depart. The fewest flights depart on a Sunday.

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.

How long does a flight from Houston Hobby Airport to Chicago Midway Airport take?

Nonstop flights from Houston Hobby Airport generally make it to Chicago Midway Airport in 2h 30m. The flying distance between the two cities is 938 miles.

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 5:05 am and will be landing in Chicago Midway Airport at 7:30 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

$73
Best time to beat the crowds with an average 44% 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 $73 for a one-way ticket and $140 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, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Houston to Chicago are Southwest and Delta. With an average price for the route of $330 and an overall rating of 8.1, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $575 and an overall rating of 8.0.

  • 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 6075 reviews
7.3Food
8.1Comfort
8.7Crew
8.3Boarding
7.8Entertainment
Airline reviews

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!

2.0 MediocreChristine, May 2024TPA - MDW
Read more about Southwest reviews

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.

Pros: "The ease of being able to switch my flight last minute"
Cons: "You could tell it was the end of the day for some employees"
Pros: "I like the boarding process. I like free checked bags."
Cons: "The wifi didn’t work. Not even able to watch a movie."
Cons: "Took an hour at Phoenix Sky Airport and 40 minutes at Midway Chicago to get luggage. Ridiculous Takes Southwest Air forever to deliver luggage"

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

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.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

I didn’t like that I could not select my seat and was assigned a seat when I checked in at LAX

Great experience overall. Check in at Austin was congested as they only have about 6 check in kiosks, one was broken, and there was a lot of Spring Break travelers.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

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!!

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 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.

I paid for extra leg room. The flimsy plastic seat underneath the floatation seat did not line up with the arm rests. It seemed as if the plastic part was zip tied on but immovable. This caused severe uncomfortable for the duration of the flight.

Plane was clean but they do not allow bag drop until 1 hour before flight. Just encouraging late fees and other issues. The worst I have experienced. Total hostage situation, pay or you miss your flight.

Everything was good, and most importantly on time. They have been extremely tardy in some of my flights

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.
5/14Tue
1 stopFrontier
6h 06mHOU-MDW
$73
6/8Sat
1 stopFrontier
11h 57mHOU-MDW
$74
5/14Tue
1 stopFrontier
6h 06mHOU-MDW
$78
6/10Mon
1 stopAllegiant Air
5h 40mHOU-MDW
$122
6/18Tue
1 stopDelta
4h 38mHOU-MDW
$139
6/3Mon
1 stopAllegiant Air
5h 27mHOU-MDW
$152
5/30Thu
2 stops
23h 48mHOU-MDW
$192
6/25Tue
1 stopDelta
4h 55mHOU-MDW
$198
5/27Mon
2 stopsSun Country Air
21h 30mHOU-MDW
$285
5/30Thu
3 stops
25h 42mHOU-MDW
$414

Search by stops

Search by airline

Search by price

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.
5/13Mon
multi-stopFrontier
19h 34mHOU-MDW
5/20Mon
multi-stopFrontier
8h 30mMDW-HOU
$235
5/10Fri
multi-stopFrontier
23h 24mHOU-MDW
5/14Tue
multi-stopFrontier
9h 39mMDW-HOU
$249
5/13Mon
multi-stopFrontier
19h 34mHOU-MDW
5/16Thu
multi-stopFrontier
10h 28mMDW-HOU
$254
5/10Fri
multi-stopFrontier
23h 24mHOU-MDW
5/30Thu
multi-stopFrontier
10h 28mMDW-HOU
$271
5/13Mon
nonstopSouthwest
2h 30mHOU-MDW
5/15Wed
nonstopSouthwest
2h 30mMDW-HOU
$412
5/13Mon
multi-stopSouthwest
4h 05mHOU-MDW
5/15Wed
nonstopSouthwest
2h 30mMDW-HOU
$417
5/13Mon
multi-stopSouthwest
4h 00mHOU-MDW
5/15Wed
multi-stopSouthwest
4h 40mMDW-HOU
$435
5/11Sat
multi-stopDelta
5h 57mHOU-MDW
5/14Tue
multi-stopDelta
5h 42mMDW-HOU
$448
5/11Sat
multi-stopDelta
5h 57mHOU-MDW
5/13Mon
multi-stopDelta
5h 42mMDW-HOU
$568
5/9Thu
multi-stopDelta
5h 51mHOU-MDW
5/14Tue
multi-stopDelta
6h 29mMDW-HOU
$572

Search by stops

Search by airline

Search by price

Houston Hobby Airport - Chicago Midway Airport Flights

Departure:

Houston Hobby Airport (undefined)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Houston Hobby Airport

Cabin classes:

$750