CA $135 Cheap Flights from Chicago (MDW) to Houston (HOU)

View CA $135 flight on Tue, May 19, 2026Opens 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 $135 for one-way flights and CA $285 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Jun 3 - Sat, Jun 6
MDW
Chicago
HOU
Houston
CA $285 Roundtrip, found 1 day ago
CA $285
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jun 3 from Chicago to Houston, returning Sat, Jun 6, priced at CA $285 found 1 day ago

Alternative airports near Houston

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to George Bush Intercontinental IAH. Cheapest option available. Average driving time to city centre is 24 minutes. Flights from CA $365
IAH
George Bush Intercontinental
Cheapest
Average driving time to city centre24 min
Flights from CA $365

Frequently asked questions

What is the cheapest month to fly from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby)?
February is typically the cheapest month to fly from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby), with average round-trip fares around 637 CAD. This is about 18% lower than the average price throughout the year. February often sees lower prices as it falls outside of peak holiday travel, when demand tends to decrease. Other cheap months to fly from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby) include January and September.
Which airlines fly direct from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby)?
Enter MDW to HOU and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby)?
To find a cheap flight from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby)?
The best airline to fly with from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby) will differ from traveler to traveler. If you like to fly early, WN offers early morning flights. If price is the most important factor, F9 typically offers the lowest fares. WN offers the most daily flights from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby), which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby)?
Based on booking data from the past year, the best time to find a good deal on a round-trip flight from Chicago, IL (MDW-Midway Intl.) (MDW) to Houston, TX (HOU-William P. Hobby) (HOU) is typically in January or February. During these months, you can expect average prices around 637 CAD. While these might not be the absolute busiest travel times, they offer a great balance of lower fares and still provide plenty of flight options for your trip.
How many flights per day from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby)?
There are approximately 6 nonstop flights per day from Chicago, IL (MDW-Midway Intl.) (MDW) to Houston, TX (HOU-William P. Hobby) (HOU). For even more choice, look at flights that include layovers, as there are around 123 connecting flights per day. Some common connection points include Love Field (DAL), Nashville Intl. (BNA), and Denver Intl. (DEN).
What is the earliest flight from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby)?
The earliest flight from Chicago Midway International Airport (MDW) to William P. Hobby Airport (HOU) typically departs at approximately 5:00 AM local time, operated by F9. This is a seasonal service active in April. An early departure like this can help maximize your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby)?
You'll find the most flights from Chicago, IL (MDW-Midway Intl.) (MDW) to Houston, TX (HOU-William P. Hobby) (HOU) on a Friday, with around 60 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include Southwest Airlines, Delta Air Lines, and Frontier Airlines. Fridays offer notably more flight options compared to other days of the week.
What are the most popular departure times for flights from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby)?
The most popular departure times for flights from Chicago Midway International Airport (MDW) to William P. Hobby Airport (HOU) are in the morning, between 9am and 12pm. About 24% of passengers prefer this time window. This timing works well for many travelers as it allows for a productive morning before flying, and an afternoon arrival at your destination.
How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby)?
Direct flights from MDW to HOU usually take about 2 hours 50 minutes, traveling roughly 938 miles. If you opt for a connecting flight, expect to add around 5 hours to your journey. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby)?
Select the "Business class" and "First class" filters when looking for MDW to HOU flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby) flight with Expedia?
It's easy to earn miles on a Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Houston from Midway Intl. (MDW)?
When traveling from Midway Intl. (MDW) to Houston, you can fly into William P. Hobby (HOU) and George Bush Intercontinental (IAH). Some flights may connect through major hubs like Nashville Intl. (BNA), Louisville Intl. (SDF), Detroit Metropolitan Wayne County (DTW) before reaching Houston. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby) at the last minute?
Typically, booking a last minute flight from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby) flight and hotel package?
Securing a Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby)?
If you booked your Chicago, IL (MDW-Midway Intl.) to Houston, TX (HOU-William P. Hobby) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Midway Intl.
Destination airport
William P. Hobby
Airlines serving
Delta
Roundtrip price
CA $284
Distance
1500 km
Average flight time
2 hours 58 mins

Book with confidence

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 4 airlines that cover this route. There are 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 $285 rising to CA $311.  

Here are more money-saving tips: 

  • Fly in June 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.

Chicago to Houston Flights

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