S$265 Cheap Flights from Chicago to Kelowna

View S$265 flight on Wed, 23 Jul, 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$265 for one-way flights and S$566 for return, for the period specified. Prices and availability are subject to change. Additional terms apply.
Air Canada
Mon, 21 Jul - Mon, 28 Jul
ORD
Chicago
YLW
Kelowna
S$566
Return
Found 3 days ago
Select Air Canada flight, departing Mon, 21 Jul from Chicago to Kelowna, returning Mon, 28 Jul, priced at S$566 Found 3 days ago
Air Canada
Mon, 21 Jul - Mon, 28 Jul
ORD
Chicago
YLW
Kelowna
S$572
Return
Found 3 days ago
Select Air Canada flight, departing Mon, 21 Jul from Chicago to Kelowna, returning Mon, 28 Jul, priced at S$572 Found 3 days ago
WestJet
Wed, 23 Jul - Wed, 30 Jul
ORD
Chicago
YLW
Kelowna
S$579
Return
Found 1 day ago
Select WestJet flight, departing Wed, 23 Jul from Chicago to Kelowna, returning Wed, 30 Jul, priced at S$579 Found 1 day ago
Air Canada
Mon, 21 Jul - Mon, 28 Jul
ORD
Chicago
YLW
Kelowna
S$585
Return
Found 3 days ago
Select Air Canada flight, departing Mon, 21 Jul from Chicago to Kelowna, returning Mon, 28 Jul, priced at S$585 Found 3 days ago
Air Canada
Mon, 21 Jul - Mon, 28 Jul
ORD
Chicago
YLW
Kelowna
S$596
Return
Found 3 days ago
Select Air Canada flight, departing Mon, 21 Jul from Chicago to Kelowna, returning Mon, 28 Jul, priced at S$596 Found 3 days ago
Air Canada
Mon, 21 Jul - Mon, 28 Jul
ORD
Chicago
YLW
Kelowna
S$601
Return
Found 3 days ago
Select Air Canada flight, departing Mon, 21 Jul from Chicago to Kelowna, returning Mon, 28 Jul, priced at S$601 Found 3 days ago
United
Mon, 21 Jul - Mon, 28 Jul
ORD
Chicago
YLW
Kelowna
S$601
Return
Found 3 days ago
Select United flight, departing Mon, 21 Jul from Chicago to Kelowna, returning Mon, 28 Jul, priced at S$601 Found 3 days ago
WestJet
Wed, 23 Jul - Wed, 30 Jul
ORD
Chicago
YLW
Kelowna
S$602
Return
Found 1 day ago
Select WestJet flight, departing Wed, 23 Jul from Chicago to Kelowna, returning Wed, 30 Jul, priced at S$602 Found 1 day ago
Air Canada
Mon, 21 Jul - Mon, 28 Jul
ORD
Chicago
YLW
Kelowna
S$606
Return
Found 3 days ago
Select Air Canada flight, departing Mon, 21 Jul from Chicago to Kelowna, returning Mon, 28 Jul, priced at S$606 Found 3 days ago
American Airlines
Mon, 21 Jul - Mon, 28 Jul
ORD
Chicago
YLW
Kelowna
S$2,580
Return
Found 3 days ago
Select American Airlines flight, departing Mon, 21 Jul from Chicago to Kelowna, returning Mon, 28 Jul, priced at S$2,580 Found 3 days ago
Chicago to Kelowna route information
Origin airport
O'Hare Intl.
Destination airport
Kelowna Intl.
Return price
S$566
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 WestJet, Air Canada, United, 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$265 and roundtrip prices from S$566*.
 

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$566. 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.

Explore a world of travel with Expedia

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