Cheap Flights to Regional District of Okanagan-Similkameen from $58 (2026/2027)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Regional District of Okanagan-Similkameen's top cities

A town by a lake surrounded by hills.

Osoyoos

Flights
Osoyoos

How Much Does it Cost To Fly To Regional District of Okanagan-Similkameen?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Oct 24 - Sat, Oct 31
YVR
Vancouver Intl.
YLW
Kelowna Intl.
$116 Roundtrip, found 4 days ago
$116
Roundtrip
found 4 days ago
Select Air North flight, departing Sat, Oct 24 from Vancouver Intl. to Kelowna Intl., returning Sat, Oct 31, priced at $116 found 4 days ago
Thu, Feb 4 - Wed, Feb 10
YVR
Vancouver Intl.
YYF
Penticton Regional
$212 Roundtrip, found 11 hours ago
$212
Roundtrip
found 11 hours ago
Select Pacific Coastal Airlines flight, departing Thu, Feb 4 from Vancouver Intl. to Penticton Regional, returning Wed, Feb 10, priced at $212 found 11 hours ago
Fri, Jan 22 - Sun, Jan 31
SEA
Seattle - Tacoma Intl.
YLW
Kelowna Intl.
$268 Roundtrip, found 1 hour ago
$268
Roundtrip
found 1 hour ago
Select WestJet flight, departing Fri, Jan 22 from Seattle - Tacoma Intl. to Kelowna Intl., returning Sun, Jan 31, priced at $268 found 1 hour ago
Fri, Oct 16 - Thu, Oct 22
YXX
Abbotsford Intl.
YLW
Kelowna Intl.
$275 Roundtrip, found 6 days ago
$275
Roundtrip
found 6 days ago
Select WestJet flight, departing Fri, Oct 16 from Abbotsford Intl. to Kelowna Intl., returning Thu, Oct 22, priced at $275 found 6 days ago
Tue, Mar 9 - Mon, Mar 15
MSP
Minneapolis - St. Paul Intl.
YLW
Kelowna Intl.
$337 Roundtrip, found 8 hours ago
$337
Roundtrip
found 8 hours ago
Select Air Canada flight, departing Tue, Mar 9 from Minneapolis - St. Paul Intl. to Kelowna Intl., returning Mon, Mar 15, priced at $337 found 8 hours ago
Thu, Feb 4 - Wed, Feb 10
YXX
Abbotsford Intl.
YYF
Penticton Regional
$341 Roundtrip, found 11 hours ago
$341
Roundtrip
found 11 hours ago
Select WestJet flight, departing Thu, Feb 4 from Abbotsford Intl. to Penticton Regional, returning Wed, Feb 10, priced at $341 found 11 hours ago
Thu, Dec 3 - Sun, Dec 6
YYZ
Pearson Intl.
YLW
Kelowna Intl.
$354 Roundtrip, found 6 days ago
$354
Roundtrip
found 6 days ago
Select Air Canada flight, departing Thu, Dec 3 from Pearson Intl. to Kelowna Intl., returning Sun, Dec 6, priced at $354 found 6 days ago
Fri, Oct 30 - Sun, Nov 1
SFO
San Francisco Intl.
YLW
Kelowna Intl.
$374 Roundtrip, found 22 hours ago
$374
Roundtrip
found 22 hours ago
Select Air Canada flight, departing Fri, Oct 30 from San Francisco Intl. to Kelowna Intl., returning Sun, Nov 1, priced at $374 found 22 hours ago
Sat, Jan 23 - Sat, Jan 30
DEN
Denver Intl.
YLW
Kelowna Intl.
$411 Roundtrip, found 1 day ago
$411
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Sat, Jan 23 from Denver Intl. to Kelowna Intl., returning Sat, Jan 30, priced at $411 found 1 day ago
OriginDestinationTravel DatesFlights From*
YEGKelownaOctober 24 to October 30$111
YVRKelownaNovember 2 to November 9$117
YYCKelownaDecember 25 to January 3$142
YYJKelownaNovember 24 to December 1$145
YVRPentictonOctober 22 to October 25$247
SEAKelownaJanuary 12 to January 17$277
YYZKelownaDecember 3 to December 6$354
YYJPentictonNovember 13 to November 16$365
LAXKelownaDecember 15 to January 5$445
YEGPentictonOctober 24 to October 30$455
YQMKelownaDecember 3 to December 10$463
YYZPentictonNovember 27 to November 28$568
YYCPentictonDecember 23 to December 29$587
SEAPentictonNovember 4 to November 5$648
PHLKelownaNovember 24 to December 1$775
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
YEGKelownaOctober 11 to October 18$162
YYCKelownaOctober 10 to October 11$237
YVRKelownaOctober 11 to October 11$239
YVRPentictonOctober 10 to October 13$474
YYZKelownaOctober 11 to October 21$667
SEAKelownaOctober 10 to October 14$826
LAXKelownaOctober 10 to October 19$834
YYCPentictonOctober 10 to October 13$925
YYZPentictonOctober 10 to October 13$1,221
SEAPentictonOctober 9 to October 12$1,682
*Prices include taxes and fees

Best Regional District of Okanagan-Similkameen Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Villa's At Eldorado Resort
4.0-star property

Villa's At Eldorado Resort

Dec 21 - Dec 26

5 night stay

Winnipeg (YWG) to Kelowna (YLW)

WestJet • Non-stop roundtrip • Coach
Price was $1,621, price is now $1,355 per person
$1,355
per person
found 1 day ago
Grizzly Ridge Getaway Brand New, Hot Tub, Sleeps 11
4.0-star property

Grizzly Ridge Getaway Brand New, Hot Tub, Sleeps 11

Dec 21 - Dec 26

5 night stay

Winnipeg (YWG) to Kelowna (YLW)

WestJet • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,874, price is now $2,297 per person
$2,297
per person
found 1 day ago
Winter Escape On Perfection Pool Hot Tub
2.0-star property

Winter Escape On Perfection Pool Hot Tub

Dec 21 - Dec 26

5 night stay

Winnipeg (YWG) to Kelowna (YLW)

WestJet • Non-stop roundtrip • Coach
Price was $1,911, price is now $1,573 per person
$1,573
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Winnipeg to Regional District of Okanagan-Similkameen
View all trips

Travelers ❤️ These Regional District of Okanagan-Similkameen 🏨

Walnut Beach Resort

Walnut Beach Resort

4 out of 5
4200 Lakeshore Dr Osoyoos BC
Book a stay at this beach hotel in Osoyoos. Enjoy free WiFi, free parking, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions sẃiẃs Provincial Park and Tumbleweed Spirits are located nearby.
9.2/10 Wonderful! (1,700 reviews)
"The property is starting to get a little dated, but in a very minor way. It’s still a beautiful property that’s a perfect location for a getaway. The views are great, everything is clean and well organized. We particularly liked the secure underground parking. Very convenient. The restaurant is very ..."

Reviewed on Oct 8, 2026

Opens in a new windowWalnut Beach Resort
Sandman Hotel Penticton

Sandman Hotel Penticton

3 out of 5
939 Burnaby Ave W Penticton BC
Book a stay at this business-friendly hotel in Penticton. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Roll N Stones Fun Centre and Penticton Community Centre are located nearby.
Opens in a new windowSandman Hotel Penticton
Watermark Beach Resort

Watermark Beach Resort

4 out of 5
15 Park Place Osoyoos BC
Book a stay at this beach hotel in Osoyoos. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the restaurant in our reviews. Popular attractions Gyro Beach and Osoyoos and District Museum and Archives are located nearby.
9.6/10 Exceptional! (1,365 reviews)
"Friendly staff very nice accommodations great view of the lake"

Reviewed on Oct 7, 2026

Opens in a new windowWatermark Beach Resort
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Balcomo, a Ramada by Wyndham

Balcomo, a Ramada by Wyndham

3 out of 5
1050 Eckhardt Ave. West Penticton BC
Book a stay at this golf hotel in Penticton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Roll N Stones Fun Centre and South Okanagan Events Centre are located nearby.
Opens in a new windowBalcomo, a Ramada by Wyndham
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Okanagan-Similkameen?
To give you an idea of prices, the cheapest roundtrip flight to Okanagan-Similkameen cost $111 within the last seven days. An easy way to score a good deal is to be flexible with your dates. This price was available on Travelocity for flights to Okanagan-Similkameen departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Okanagan-Similkameen?
According to Travelocity's direct return flight demand between January and December last year, October is the cheapest month to board a plane to Okanagan-Similkameen. Search for flights throughout this month and get a terrific deal today.
How can I check my flight status to Okanagan-Similkameen?
Go to our helpful customer portal, Trips. You'll find everything related to your flight to Okanagan-Similkameen here, including details about flight delays, gate changes and more. You can find Trips at the top of the Travelocity homepage. Simply create your free account and find the answers you're after. Alternatively, you can access your itinerary on the move and get real-time travel updates with the Travelocity app. All your itineraries are in one convenient place, making it easy to share details with any members of your family flying with you.
How do I find the best deals on flights to Okanagan-Similkameen?
There are several ways — book ahead of time, avoid vacation periods and be flexible with your dates. If your dates aren't set in stone, search for your flight to Okanagan-Similkameen on Travelocity and hit "Flexible dates" above your results. This will show you any cheaper airfares on a nearby day. $111 was the lowest price paid for a return flight to Okanagan-Similkameen in the last seven days. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Okanagan-Similkameen with Travelocity?
Look for cheap flights to Okanagan-Similkameen with Travelocity and begin packing for your next break. With round-the-clock customer support before, during and after your trip and our Price Match Guarantee, we take the difficulty out of finding cheap family flights, places to stay and more. Score a top deal today and get ready for the adventure of your dreams.
How much is a flight to Okanagan-Similkameen on average?
Based on prices found over the last seven days, roundtrip flights to Okanagan-Similkameen cost between $111 and $1,682. Whenever you're ready to take off, Travelocity will help you find a fare that'll fit your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What can I expect on a flight to Okanagan-Similkameen?
That mainly depends on where you're traveling from and which airline you take off with. You'll likely find all kinds of flights to Okanagan-Similkameen, from business class trips to cheap flights for family vacations. Most airlines on long-haul flights generally offer food and drinks, a variety of entertainment programs as well as games to keep your little ones busy.