S$233 Cheap Flights from Chicago to Kelowna

View S$233 flight on Mon, 18 Aug, 2025Opens in a new window

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

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Cheap Flights from Chicago to Kelowna (ORD-YLW)

Prices were available within the past 7 days and start at S$233 for one-way flights and S$491 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

WestJet
Fri, 22 Aug - Fri, 29 Aug
ORD
Chicago
YLW
Kelowna
S$491 Return, found 12 hours ago
S$491
Return
found 12 hours ago
Select WestJet flight, departing Fri, 22 Aug from Chicago to Kelowna, returning Fri, 29 Aug, priced at S$491 found 12 hours ago
WestJet
Mon, 18 Aug - Mon, 25 Aug
ORD
Chicago
YLW
Kelowna
S$499 Return, found 4 days ago
S$499
Return
found 4 days ago
Select WestJet flight, departing Mon, 18 Aug from Chicago to Kelowna, returning Mon, 25 Aug, priced at S$499 found 4 days ago
Air Canada
Mon, 18 Aug - Mon, 25 Aug
ORD
Chicago
YLW
Kelowna
S$500 Return, found 4 days ago
S$500
Return
found 4 days ago
Select Air Canada flight, departing Mon, 18 Aug from Chicago to Kelowna, returning Mon, 25 Aug, priced at S$500 found 4 days ago
Air Canada
Mon, 18 Aug - Mon, 25 Aug
ORD
Chicago
YLW
Kelowna
S$518 Return, found 4 days ago
S$518
Return
found 4 days ago
Select Air Canada flight, departing Mon, 18 Aug from Chicago to Kelowna, returning Mon, 25 Aug, priced at S$518 found 4 days ago
Air Canada
Mon, 18 Aug - Mon, 25 Aug
ORD
Chicago
YLW
Kelowna
S$526 Return, found 4 days ago
S$526
Return
found 4 days ago
Select Air Canada flight, departing Mon, 18 Aug from Chicago to Kelowna, returning Mon, 25 Aug, priced at S$526 found 4 days ago
Air Canada
Fri, 22 Aug - Fri, 29 Aug
ORD
Chicago
YLW
Kelowna
S$528 Return, found 12 hours ago
S$528
Return
found 12 hours ago
Select Air Canada flight, departing Fri, 22 Aug from Chicago to Kelowna, returning Fri, 29 Aug, priced at S$528 found 12 hours ago
WestJet
Mon, 18 Aug - Mon, 25 Aug
ORD
Chicago
YLW
Kelowna
S$530 Return, found 4 days ago
S$530
Return
found 4 days ago
Select WestJet flight, departing Mon, 18 Aug from Chicago to Kelowna, returning Mon, 25 Aug, priced at S$530 found 4 days ago
WestJet
Fri, 22 Aug - Fri, 29 Aug
ORD
Chicago
YLW
Kelowna
S$530 Return, found 12 hours ago
S$530
Return
found 12 hours ago
Select WestJet flight, departing Fri, 22 Aug from Chicago to Kelowna, returning Fri, 29 Aug, priced at S$530 found 12 hours ago
United
Fri, 22 Aug - Fri, 29 Aug
ORD
Chicago
YLW
Kelowna
S$548 Return, found 12 hours ago
S$548
Return
found 12 hours ago
Select United flight, departing Fri, 22 Aug from Chicago to Kelowna, returning Fri, 29 Aug, priced at S$548 found 12 hours ago
American Airlines
Fri, 22 Aug - Fri, 29 Aug
ORD
Chicago
YLW
Kelowna
S$2,704 Return, found 12 hours ago
S$2,704
Return
found 12 hours ago
Select American Airlines flight, departing Fri, 22 Aug from Chicago to Kelowna, returning Fri, 29 Aug, priced at S$2,704 found 12 hours ago

Find the cheapest month to fly from Chicago (ORD) to Kelowna (YLW)

May is typically the cheapest month to fly

From S$255 - S$741 per traveller.

Graph displaying average flight prices per month

Chicago to Kelowna route information
Origin airport
O'Hare Intl.
Destination airport
Kelowna Intl.
Airlines serving
Air Canada, American Airlines, United, WestJet
Return price
S$491
Distance
2551 km

Perfect flights from Chicago to Kelowna

Your Journey from Chicago to Kelowna

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to Kelowna caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Air Canada, WestJet, United, Delta, Alaska Airlines, American Airlines. Our selection of flights from O'Hare Intl. to Kelowna Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Chicago to Kelowna Flights

Experience the joy of finding cheap flights from O'Hare Intl. to Kelowna Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$233 and roundtrip prices from S$491*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to Kelowna with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Kelowna

Picture yourself stepping off the plane in Kelowna and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Chicago to Kelowna Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Chicago to Kelowna.
 

Beyond the Flight – Exploring Kelowna

With Expedia, your adventure extends beyond the flight. Explore Kelowna at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Chicago to Kelowna with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Chicago to Kelowna with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from O'Hare Airport to Kelowna Intl. Airport (YLW)?
Round-trip journeys from O'Hare Intl. Airport (ORD) to Kelowna Intl. Airport start from S$491. This is based on fares quoted within the last 7 days on Expedia for flights departing within the next year --- make your booking ASAP to avoid missing out. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from ORD to Kelowna Intl. Airport?
Most flights can be cancelled online, but every airline has different terms and conditions. If you do have to cancel your flight, visit our Customer Service Portal and follow the instructions.
How do I find cheap flights from O'Hare Intl. Airport (ORD) to Kelowna Intl. Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for ORD to Kelowna Intl. Airport (YLW) flights, you'll see a "no change fees" filter for you to select.
How many hours is the flight from ORD to Kelowna Intl. Airport (YLW)?
You may like to bring your own on-board entertainment, as it takes about 6 hours and 12 minutes to fly to Kelowna Intl. Airport from ORD. A set of noise-cancelling headphones will be handy too.
How far is the flight from ORD to YLW?
Around 2,600 kilometres separates Chicago and Kelowna, so pack something to help you while away a couple of hours. That novel you've yet to start will be just the ticket.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Kelowna Intl. Airport?
Direct flights aren't available, so you'll need to make at least one stop between O'Hare Intl. Airport (ORD) and Kelowna Intl. Airport (YLW). Take advantage of the layover time to stretch your legs and enjoy some personal space.
Are O'Hare Airport to Kelowna Intl. Airport (YLW) flight tickets cheaper when they're purchased at the last minute?
Booking your trip from ORD to YLW at the last minute could be your ticket to a cheap deal. However, it could end up costing a good deal more! If you'd rather avoid the risk, book well ahead of your departure date. In fact, Expedia has some of the best bargains as far ahead as 12 months in advance. If your preferred carrier hasn't released tickets yet, check back regularly as deals are updated on Expedia all the time.

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