$69 Cheap Flights from Houston (HOU) to Chicago (ORD)

View $69 flight on Fri, Feb 20, 2026Opens in a new window

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

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Cheap Flights from Houston to Chicago (HOU-ORD)

Prices were available within the past 7 days and start at $69 for one-way flights and $137 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Feb 19 - Sat, Feb 21
HOU
Houston
ORD
Chicago
$137 Roundtrip, found 19 hours ago
$137
Roundtrip
found 19 hours ago
Select Southwest Airlines flight, departing Thu, Feb 19 from Houston to Chicago, returning Sat, Feb 21, priced at $137 found 19 hours ago
Sun Country Airlines
Wed, Nov 26 - Fri, Nov 28
HOU
Houston
ORD
Chicago
$323 Roundtrip, just found
$323
Roundtrip
just found
Select Sun Country Airlines flight, departing Wed, Nov 26 from Houston to Chicago, returning Fri, Nov 28, priced at $323 just found

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

February is typically the cheapest month to fly

From $57 - $395 per traveler.

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. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $125
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $125

Frequently asked questions

How much does a flight from William P. Hobby Airport (HOU) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight from $69 or cheap return flight from $137 from William P. Hobby Airport (HOU) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from William P. Hobby Airport (HOU) to O'Hare Intl. Airport (ORD)?
February is the most affordable month to fly from HOU to ORD. Avoiding peak travel times is often the key to landing a great deal.
Which airlines fly direct from William P. Hobby Airport (HOU) to O'Hare Intl. Airport (ORD)?
Although Houston, TX (HOU-William P. Hobby) has no direct flights to O'Hare Intl. Airport (ORD), other airports have nonstop options. Taking off from George Bush Intercontinental Airport (IAH) will get you to Chicago without any detours.
What is the cheapest airline that flies from William P. Hobby Airport (HOU) to O'Hare Intl. Airport (ORD)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest HOU to ORD flight.
How many flights per day from William P. Hobby Airport (HOU) to O'Hare Intl. Airport (ORD)?
Direct flights from William P. Hobby Airport (HOU) to O'Hare Intl. Airport (ORD) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filters. Enter your dates and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from HOU to ORD?
Generally you'll have the most choice when it comes to flights on a Friday. Tuesdays are often the quietest.* But this can change based on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from William P. Hobby Airport (HOU) to O'Hare Intl. Airport (ORD)?
To touch down at O'Hare Intl. Airport (ORD) on schedule, book a flight that leaves from William P. Hobby Airport (HOU) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from William P. Hobby Airport (HOU)?
If you're taking a direct flight from William P. Hobby Airport (HOU) to Chicago, Midway Intl. Airport (MDW) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from William P. Hobby Airport (HOU) to O'Hare Intl. Airport (ORD) last-minute?
Holding off until just before your trip to book a ticket from HOU to ORD often results in higher prices. Although you may find some last-minute offers, they aren't always guaranteed. Be flexible with your travel plans for the best chance of getting a bargain.
Is it cheaper to book a HOU to ORD flight and hotel package?
You can save money by securing a HOU to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. After selecting your ideal accommodations and flights, consider other add-ons like tours, car rentals and activities.
Can I cancel or change the date of my flight from William P. Hobby Airport (HOU) to O'Hare Intl. Airport (ORD)?
If you booked your HOU to ORD flight in the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for more details.

Travel information

Origin airport
William P. Hobby
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Southwest Airlines, Sun Country Airlines
Roundtrip price
$136
Distance
945 mi

Book with confidence

Houston to Chicago Flights

The cheapest times to fly from Houston to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Houston to Chicago are during the month of February. You can find some of the cheapest flights from Houston to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Houston to Chicago

Sunday is one of the best days to book for cheap flights from Houston to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Houston to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Houston to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $69 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Houston to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Houston to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Houston to Chicago Flights

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*Available to One Key members.