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

HOU - MDW

$80 Find cheap flights from Houston Hobby Airport to Chicago Midway 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 Hobby to Midway departing on 6/4. 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
jue. 6/27
jue. 7/4

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 42,816,550 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
3:46 pm - 12:00 pmHOU-MDW
20h 14m1 stop
10:26 pm - 9:04 amMDW-HOU
10h 38m1 stop
$141Frontier
Find Deal
mar., jun. 11 - sáb., jun. 15
12:50 pm - 1:09 pmHOU-MDW
24h 19m1 stop
5:55 am - 8:53 amMDW-HOU
26h 58m1 stop
$150Frontier
Find Deal
lun., jun. 10 - mié., jun. 12
10:44 pm - 11:08 amHOU-MDW
12h 24m1 stop
10:26 pm - 9:04 amMDW-HOU
10h 38m1 stop
$158Frontier
Find Deal
mié., jun. 12 - sáb., jun. 15
9:35 am - 9:30 pmHOU-MDW
11h 55m1 stop
6:00 am - 2:55 pmMDW-HOU
8h 55m1 stop
$170Frontier
Find Deal
sáb., jun. 15 - mar., jun. 18
12:50 pm - 5:10 pmHOU-MDW
28h 20m1 stop
8:51 pm - 8:17 pmMDW-HOU
23h 26m1 stop
$177Frontier
Find Deal
lun., jun. 10 - jue., jun. 13
9:35 am - 9:30 pmHOU-MDW
11h 55m1 stop
6:00 am - 2:55 pmMDW-HOU
8h 55m1 stop
$183Frontier
Find Deal
sáb., jun. 15 - mar., jun. 18
9:33 am - 11:12 amHOU-MDW
25h 39m1 stop
5:55 am - 8:53 amMDW-HOU
26h 58m1 stop
$185Frontier
Find Deal
sáb., jun. 8 - mié., jun. 12
2:30 pm - 9:31 amHOU-MDW
19h 01m1 stop
5:55 am - 9:52 pmMDW-HOU
15h 57m1 stop
$186Frontier
Find Deal
mié., jun. 12 - mié., jun. 19
4:20 pm - 9:44 pmHOU-MDW
5h 24m1 stop
10:11 am - 3:33 pmMDW-HOU
5h 22m1 stop
$447Delta
Find Deal
mié., sep. 11 - lun., sep. 16
4:20 pm - 9:44 pmHOU-MDW
5h 24m1 stop
1:05 pm - 6:26 pmMDW-HOU
5h 21m1 stop
$498Delta
Find Deal
mar., sep. 10 - mar., sep. 17

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 Sunday and avoid Fridays if you are looking for the best rates. For your return to Houston Hobby Airport, you’ll find the best rates on Saturdays 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 $127 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.

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 ($141) and Delta ($447). Frontier proposed the cheapest one-way flight at $80.

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 4 and 6 nonstop flights that take off from Houston Hobby Airport and land in Chicago Midway Airport, with an average flight time of 2h 30m. The most common departure time is 6:00 pm and most flights take off in the evening. Each week, there are 39 flights. The most frequent day of departure is Tuesday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.

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.

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 5:45 am and will be landing in Chicago Midway Airport at 8:10 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

$80
Best time to beat the crowds with an average 43% 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 $80 for a one-way ticket and $141 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, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Houston to Chicago are Delta and Frontier. With an average price for the route of $577 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 $149 and an overall rating of 6.2.

  • 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 5984 reviews
8.3Boarding
8.1Comfort
7.3Food
7.8Entertainment
8.7Crew
Airline reviews

Our first flight was so delayed that we had 10 mins to board the next one. We requested if the flight attendant could allow us off there plane first and they denied our request even though I have seen this done before. Luck was on our side that we didn’t miss our next flight.

2.0 MediocreRubi, May 2024HOU - SAN
Read more about Southwest reviews

Our first flight was so delayed that we had 10 mins to board the next one. We requested if the flight attendant could allow us off there plane first and they denied our request even though I have seen this done before. Luck was on our side that we didn’t miss our next flight.

Delay after delay after delay. Very disappointing I am about ready to give up on Southwest. One of the crewmembers sat and played games on her phone for the entire trip from Chicago to Baltimore. Unbelievable, very unprofessional, and very disappointing.

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"

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.

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

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 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.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

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.

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

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.

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.
6/4mar.
1 stopFrontier
13h 08mHOU-MDW
$80
6/2dom.
1 stopFrontier
12h 45mHOU-MDW
$90
7/23mar.
1 stopFrontier
5h 35mHOU-MDW
$100
6/21vie.
1 stopFrontier
10h 47mHOU-MDW
$106
8/27mar.
1 stopFrontier
16h 22mHOU-MDW
$109
8/1jue.
1 stopFrontier
12h 04mHOU-MDW
$111
7/1lun.
1 stopDelta
4h 38mHOU-MDW
$199
6/2dom.
2 stops
23h 28mHOU-MDW
$254
10/18vie.
1 stopDelta
7h 29mHOU-MDW
$298
7/1lun.
2 stopsDelta
6h 48mHOU-MDW
$454

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.
6/1sáb.
multi-stopFrontier
11h 08mHOU-MDW
6/4mar.
multi-stopFrontier
16h 02mMDW-HOU
$139
6/1sáb.
multi-stopFrontier
11h 08mHOU-MDW
6/6jue.
multi-stopFrontier
13h 16mMDW-HOU
$140
6/1sáb.
multi-stopFrontier
11h 08mHOU-MDW
6/5mié.
multi-stopFrontier
15h 57mMDW-HOU
$150
6/1sáb.
multi-stopFrontier
11h 08mHOU-MDW
6/4mar.
multi-stopFrontier
7h 17mMDW-HOU
$152
6/1sáb.
multi-stopFrontier
11h 08mHOU-MDW
6/3lun.
multi-stopFrontier
8h 40mMDW-HOU
$177
6/1sáb.
multi-stopFrontier
11h 08mHOU-MDW
6/2dom.
multi-stopFrontier
14h 52mMDW-HOU
$249
5/31vie.
multi-stopAllegiant Air
5h 27mHOU-MDW
6/3lun.
multi-stopAllegiant Air
5h 16mMDW-HOU
$337
5/30jue.
multi-stop
23h 48mHOU-MDW
6/3lun.
multi-stop
5h 16mMDW-HOU
$558
5/31vie.
multi-stopDelta
4h 46mHOU-MDW
6/4mar.
multi-stopDelta
6h 29mMDW-HOU
$667
5/29mié.
multi-stopDelta
5h 26mHOU-MDW
5/31vie.
multi-stopDelta
6h 29mMDW-HOU
$712

Search by stops

Search by airline

Search by price

Houston Hobby Airport - Chicago Midway Airport Flights

Departure:

Houston Hobby Airport (HOU)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Houston Hobby Airport

Cabin classes:

$750