CA $149 Cheap Flights from Chicago (MDW) to Houston (HOU)

View CA $149 flight on Sat, Oct. 11, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Houston William Hobby Airport (HOU)

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Cheap flights from Chicago (MDW) to Houston (HOU)

Prices were available within the past 7 days and start at CA $149 for one-way flights and CA $377 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Oct. 18 - Sat, Oct. 25
MDW
Chicago
HOU
Houston
CA $377 Roundtrip, found 3 days ago
CA $377
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Oct. 18 from Chicago to Houston, returning Sat, Oct. 25, priced at CA $377 found 3 days ago

Find the cheapest month to fly from Chicago (MDW) to Houston (HOU)

October is typically the cheapest month to fly

From CA $98 - CA $373 per traveller.

Graph displaying average flight prices per month

Flight from Chicago to Houston (MDW - HOU) route information
Origin airport
Midway Intl.
Destination airport
William P. Hobby
Airlines serving
Delta
Roundtrip price
CA $376
Distance
1500 km
Average flight time
2 hours 33 mins

Chicago to Houston Flights

The easy way to book your flights from Chicago to Houston 

With Expedia, it’s simple to find and book flights to Houston from Chicago whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 3 airlines that cover this route. There are Southwest Airlines nonstop flights to William P. Hobby, too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Chicago to Houston today, tomorrow, or this week.  

 

Save dollars with cheap flights from Midway Intl., MDW to William P. Hobby, HOU 

Sort your search results by price to find great deals on your flight from Chicago to Houston—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Houston from Chicago currently is just CA $377 rising to CA $377.  

Here are more money-saving tips: 

  • Fly in October when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Houston  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Houston from Chicago 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Houston with Expedia today.

Frequently asked questions

How much is a flight from Midway Airport to William P. Hobby Airport (HOU)?
If you're planning on travelling between Midway Intl. Airport (MDW) and William P. Hobby Airport (HOU), round-trip flights start from CA $377. This figure is based on fares quoted within the last 7 days on Expedia for flights departing within the next year, so don't let a good deal slip through your fingers. Book now and save yourself money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from MDW to HOU?
The majority of flights can be cancelled online, but whether or not you incur a fee all comes down to your airline. If you do need to cancel your break, follow the instructions in the Customer Service Portal.
How do I find cheap flights from Midway Intl. Airport (MDW) to William P. Hobby Airport that have flexible change policies?
Plenty of carriers will allow you to move your flight without a change fee. All you pay is any additional cost for the new flight. When looking for MDW to William P. Hobby Airport (HOU) flights, you'll see a "No change fees" filter for you to tick.
How many hours is the flight from Midway Airport to William P. Hobby Airport (HOU)?
The flight time from Midway Intl. Airport (MDW) to William P. Hobby Airport is only 2 hours and 50 minutes. If you're lucky, you might just get through a whole movie before arriving!
How far is the flight from Midway Airport to HOU?
The flight distance between Midway Intl. Airport (MDW) and HOU is 1,500 kilometres. Work your way through your travel song playlist or make a start on the latest bestseller and the journey will zip on by.
Which airlines fly direct from Midway Intl. Airport (MDW) to William P. Hobby Airport?
Offering 121 flights every month, Southwest Airlines (WN) is a top choice when flying directly from MDW to William P. Hobby Airport (HOU).
Are Midway Intl. Airport (MDW) to HOU flight tickets cheaper when they're purchased at the last minute?
Flight prices always go up and down, so not always. While last-minute flight deals between MDW and William P. Hobby Airport (HOU) are of course possible, it's also a good idea to keep a close eye on prices well before you fly. In fact, some air carriers release their prices up to a year ahead of the departure date. Expedia is constantly updating the biggest airfare bargains around, so keep checking back and be ready to pounce when fare prices drop.

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*Available to Expedia members.