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CA $211 Cheap Flights from Houston (HOU) to Chicago (ORD)

View CA $211 flight on Wed, Nov 11, 2026Opens in a new window

Popular airlines from Houston William Hobby Airport (HOU) to Chicago O'Hare International Airport (ORD)

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

Prices were available within the past 7 days and start at CA $211 for one-way flights and CA $420 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Nov 11 - Tue, Nov 17
HOU
Houston
ORD
Chicago
CA $420 Roundtrip, found 1 day ago
CA $420
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Nov 11 from Houston to Chicago, returning Tue, Nov 17, priced at CA $420 found 1 day ago
Delta
Fri, Oct 23 - Tue, Oct 27
HOU
Houston
ORD
Chicago
CA $433 Roundtrip, found 3 days ago
CA $433
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Oct 23 from Houston to Chicago, returning Tue, Oct 27, priced at CA $433 found 3 days ago

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city centre is 16 minutes. Flights from CA $863
MDW
Midway Intl.
Closest
Average driving time to city centre16 min
Flights from CA $863

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

February is typically the cheapest month to fly

From CA $98 - CA $197 per traveller.

Frequently asked questions

How much does a flight from Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from CA $211 and cheap return flights from CA $420 HOU to ORD with Expedia. One-way flights typically cost between CA$224 and CA$886. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when HOU to ORD ticket fares go up or down.
What is the cheapest month to fly from Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.)?
The cheapest months to fly from HOU to ORD are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Houston, TX (HOU) to Chicago, IL (ORD)?
Enter HOU to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.)?
Frontier Airlines is one of the cheapest airlines offering nonstop return flights from William P. Hobby (HOU) to O'Hare Intl. (ORD), with tickets starting from around CA$77 for flights that can be booked for departure within the next year. Sun Country Airlines is one of the cheapest airlines offering connecting return flights from William P. Hobby (HOU) to O'Hare Intl. (ORD), with tickets starting from around CA$289. These prices are per adult for economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
How do I find cheap flights from Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.), 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 Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, Frontier Airlines typically offers the lowest fares. Delta offers the most daily flights from Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.), 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 Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.)?
There are approximately 26 connecting flights per day from William P. Hobby (HOU) to O'Hare Intl. (ORD). Some common connection points include Hartsfield-Jackson Atlanta Intl. (ATL), Dallas-Fort Worth Intl. (DFW), and Love Field (DAL).
What is the earliest flight from Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.) typically departs at around 5:00 AM. This service is operated by American Airlines. This is a seasonal service, active in January and December. An early departure like this can help you make the most of 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 Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.)?
You'll typically find the most flights from Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.) on a Friday, with around 88 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include United, American Airlines, and Delta. Friday offers notably more flight options compared to other days of the week, making it a great day to find a flight that fits your schedule.
What are the most popular departure times for flights from Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from William P. Hobby (HOU) to O'Hare Intl. (ORD) are in the early morning, from 6am to 9am. Many major carriers, including American Airlines, United and Southwest Airlines, offer flights during this window. Many travellers prefer these times because they can get an early start to their day in Chicago.
How long does it take to fly from Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.)?
Flying from HOU to ORD with a connection usually takes about 5 hours, traveling roughly 1,521 kilometers. 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 Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.)?
You can fly business class or first class between HOU and ORD. You can fly business class with Frontier Airlines and Delta.First class cabins are available on Alaska Airlines, Spirit Airlines, United, Delta, and American Airlines.
How do I earn miles on a Houston, TX (HOU) to Chicago, IL (ORD) flight with Expedia?
It's easy to earn miles on a Houston, TX (HOU) to Chicago, IL (ORD) 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 Chicago, IL (ORD) from Houston, TX (HOU)?
If you're planning to travel to Chicago from William P. Hobby (HOU), you can fly directly into O'Hare Intl. (ORD). Some flights may connect through major hubs like Portland Intl. (PDX), Seattle - Tacoma Intl. (SEA), or Evers Intl. (JAN) before reaching Chicago. 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 Houston, TX (HOU) to Chicago, IL (ORD) at the last minute?
Typically, booking a last minute flight from Houston, TX (HOU) to Chicago, IL (ORD) 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 Houston, TX (HOU) to Chicago, IL (ORD) flight and hotel package?
Securing a Houston, TX (HOU) to Chicago, IL (ORD) 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 Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Houston, TX (HOU-William P. Hobby) to Chicago, IL (ORD-O'Hare Intl.) 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
William P. Hobby
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta
Roundtrip price
CA $419
Distance
1512 km

Book with confidence

Houston to Chicago Flights

The easy way to book your flights from Houston to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Houston whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 9 airlines that cover this route. There are nonstop flights to O'Hare Intl., 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 Houston to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from William P. Hobby, HOU to O'Hare Intl., ORD 

Sort your search results by price to find great deals on your flight from Houston to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Houston currently is just CA $420 rising to CA $433.  

Here are more money-saving tips: 

  • Fly in November when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • 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 Chicago from Houston 

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 Chicago with Expedia today.

Houston to Chicago Flights

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