£148 Cheap Flights from Kelowna (YLW) to Chicago (ORD)

View £148 flight on Sun, 24 May 2026Opens in a new window

Popular airlines from Kelowna Intl. Airport (YLW) to Chicago O'Hare International Airport (ORD)

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Cheap Flights from Kelowna (YLW) to Chicago (ORD)

Prices were available within the past 7 days and start at £148 for one-way flights and £290 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

WestJet
Sun, 24 May - Tue, 2 Jun
YLW
Kelowna
ORD
Chicago
£290 Return, found 4 days ago
£290
Return
found 4 days ago
Select WestJet flight, departing Sun, 24 May from Kelowna to Chicago, returning Tue, 2 Jun, priced at £290 found 4 days ago
Air Canada
Tue, 8 Sept - Tue, 22 Sept
YLW
Kelowna
ORD
Chicago
£299 Return, found 1 day ago
£299
Return
found 1 day ago
Select Air Canada flight, departing Tue, 8 Sept from Kelowna to Chicago, returning Tue, 22 Sept, priced at £299 found 1 day ago
Air Canada
Tue, 8 Sept - Tue, 22 Sept
YLW
Kelowna
ORD
Chicago
£306 Return, found 1 day ago
£306
Return
found 1 day ago
Select Air Canada flight, departing Tue, 8 Sept from Kelowna to Chicago, returning Tue, 22 Sept, priced at £306 found 1 day ago
Air Canada
Tue, 9 Jun - Mon, 15 Jun
YLW
Kelowna
ORD
Chicago
£312 Return, found 2 days ago
£312
Return
found 2 days ago
Select Air Canada flight, departing Tue, 9 Jun from Kelowna to Chicago, returning Mon, 15 Jun, priced at £312 found 2 days ago
WestJet
Sun, 24 May - Tue, 2 Jun
YLW
Kelowna
ORD
Chicago
£313 Return, found 4 days ago
£313
Return
found 4 days ago
Select WestJet flight, departing Sun, 24 May from Kelowna to Chicago, returning Tue, 2 Jun, priced at £313 found 4 days ago
Air Canada
Tue, 8 Sept - Tue, 22 Sept
YLW
Kelowna
ORD
Chicago
£318 Return, found 1 day ago
£318
Return
found 1 day ago
Select Air Canada flight, departing Tue, 8 Sept from Kelowna to Chicago, returning Tue, 22 Sept, priced at £318 found 1 day ago
Air Canada
Tue, 9 Jun - Mon, 15 Jun
YLW
Kelowna
ORD
Chicago
£318 Return, found 2 days ago
£318
Return
found 2 days ago
Select Air Canada flight, departing Tue, 9 Jun from Kelowna to Chicago, returning Mon, 15 Jun, priced at £318 found 2 days ago
Alaska Airlines
Tue, 9 Jun - Mon, 15 Jun
YLW
Kelowna
ORD
Chicago
£322 Return, found 2 days ago
£322
Return
found 2 days ago
Select Alaska Airlines flight, departing Tue, 9 Jun from Kelowna to Chicago, returning Mon, 15 Jun, priced at £322 found 2 days ago
Air Canada
Tue, 8 Sept - Tue, 22 Sept
YLW
Kelowna
ORD
Chicago
£324 Return, found 1 day ago
£324
Return
found 1 day ago
Select Air Canada flight, departing Tue, 8 Sept from Kelowna to Chicago, returning Tue, 22 Sept, priced at £324 found 1 day ago
Air Canada
Tue, 9 Jun - Mon, 15 Jun
YLW
Kelowna
ORD
Chicago
£326 Return, found 2 days ago
£326
Return
found 2 days ago
Select Air Canada flight, departing Tue, 9 Jun from Kelowna to Chicago, returning Mon, 15 Jun, priced at £326 found 2 days ago

Frequently asked questions

What is the cheapest month to fly from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
September is typically the cheapest month to fly from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.), with average return fares of approximately £298. This is about 26% lower than the average price throughout the year. September often sees lower prices as the summer travel rush ends and before the holiday season begins, leading to reduced demand. Other cheap months to fly from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) include May and August.*Averages based on flights available on Expedia in the last year.
How do I find cheap flights from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Kelowna, BC (YLW-Kelowna Intl.) 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 time to fly from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best time to fly from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) is typically September or August. While we don't have specific popularity data for these months, they are historically the cheapest times to fly, with average return flights around £298. Traveling during these months can help you save on airfare, allowing you to make the most of your trip to Chicago.*Prices based on flights available on Expedia in the last year.
How many flights per day from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are approximately 20 connecting flights per day from Kelowna International (YLW) to O'Hare Intl. (ORD). Some common connection points include Vancouver Intl. (YVR), Seattle - Tacoma Intl. (SEA), and Calgary Intl. (YYC).
What is the earliest flight from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically departs at approximately 5:05 AM local time. This service is seasonal, active in April and May, and is operated by WestJet and Delta Air Lines. An early departure like this can help you maximise 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 Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You'll typically find the most flights from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) on a Sunday, with around 26 flights available. This gives you a good selection of options for your journey. Major airlines on this route include Air Canada, WestJet, and Alaska Airlines.
What are the most popular departure times for flights from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) are in the early morning, from 6am to 9am. About 23% of passengers prefer this time. Many major carriers, including WestJet, Delta and Air Canada, offer flights during this window. This timing works well because it allows you to get an early start on your travel day and arrive in Chicago with plenty of time for your activities.
How long does it take to fly from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Flying from YLW to ORD with a connection usually takes about 7 hours 20 minutes, traveling roughly 1,595 miles. 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 Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Select the "Business class" and "First class" filters when looking for YLW to ORD 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 Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) 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 from Kelowna International (YLW)?
From Kelowna International (YLW), you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW) in Chicago. Some flights may connect through major hubs like Vancouver Intl. (YVR), Calgary Intl. (YYC), Pearson Intl. (YYZ) 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 Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) 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 Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) 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 Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Kelowna, BC (YLW-Kelowna Intl.) 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
Kelowna Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, Alaska Airlines, WestJet
Return price
£290
Distance
2551 km

Book with confidence

Compare flights from Kelowna to Chicago easily and book with confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Kelowna to Chicago. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to O'Hare Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Kelowna Intl. to O'Hare Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from Kelowna Intl. (YLW) to O'Hare Intl. (ORD)

The easiest way to view the best deals on flights from Kelowna to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Kelowna Intl. to O'Hare Intl. start at just £290 and range up to £326.  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near Kelowna and Chicago
  • booking your flight during May, the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your Kelowna to Chicago flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Kelowna Intl. to O'Hare Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

Compare flights from Kelowna to Chicago easily and book with confidence

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*Available to Expedia members.