Flights To Regional District of Okanagan-Similkameen - Cheap Flights Starting at CA $58

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.

Tue, Sep 8 - Tue, Sep 8
YVR
Vancouver Intl.
YLW
Kelowna Intl.
CA $142 Roundtrip, found 3 days ago
CA $142
Roundtrip
found 3 days ago
Select WestJet flight, departing Tue, Sep 8 from Vancouver Intl. to Kelowna Intl., returning Tue, Sep 8, priced at CA $142 found 3 days ago
Tue, Sep 22 - Tue, Oct 6
YEG
Edmonton Intl.
YLW
Kelowna Intl.
CA $162 Roundtrip, found 5 hours ago
CA $162
Roundtrip
found 5 hours ago
Select Flair Airlines flight, departing Tue, Sep 22 from Edmonton Intl. to Kelowna Intl., returning Tue, Oct 6, priced at CA $162 found 5 hours ago
Sun, Sep 6 - Sun, Sep 6
YVR
Vancouver Intl.
YYF
Penticton Regional
CA $162 Roundtrip, found 4 days ago
CA $162
Roundtrip
found 4 days ago
Select WestJet flight, departing Sun, Sep 6 from Vancouver Intl. to Penticton Regional, returning Sun, Sep 6, priced at CA $162 found 4 days ago
Mon, Sep 7 - Fri, Sep 11
YYC
Calgary Intl.
YLW
Kelowna Intl.
CA $176 Roundtrip, found 1 day ago
CA $176
Roundtrip
found 1 day ago
Select Flair Airlines flight, departing Mon, Sep 7 from Calgary Intl. to Kelowna Intl., returning Fri, Sep 11, priced at CA $176 found 1 day ago
Tue, Sep 15 - Wed, Sep 16
YXX
Abbotsford Intl.
YLW
Kelowna Intl.
CA $200 Roundtrip, found 13 hours ago
CA $200
Roundtrip
found 13 hours ago
Select WestJet flight, departing Tue, Sep 15 from Abbotsford Intl. to Kelowna Intl., returning Wed, Sep 16, priced at CA $200 found 13 hours ago
Wed, Aug 19 - Wed, Aug 19
YYJ
Victoria Intl.
YLW
Kelowna Intl.
CA $229 Roundtrip, found 5 hours ago
CA $229
Roundtrip
found 5 hours ago
Select WestJet flight, departing Wed, Aug 19 from Victoria Intl. to Kelowna Intl., returning Wed, Aug 19, priced at CA $229 found 5 hours ago
Wed, Aug 26 - Mon, Aug 31
YYJ
Victoria Intl.
YYF
Penticton Regional
CA $266 Roundtrip, just found
CA $266
Roundtrip
just found
Select WestJet flight, departing Wed, Aug 26 from Victoria Intl. to Penticton Regional, returning Mon, Aug 31, priced at CA $266 just found
Fri, Jul 31 - Fri, Jul 31
YYC
Calgary Intl.
YYF
Penticton Regional
CA $279 Roundtrip, found 3 days ago
CA $279
Roundtrip
found 3 days ago
Select WestJet flight, departing Fri, Jul 31 from Calgary Intl. to Penticton Regional, returning Fri, Jul 31, priced at CA $279 found 3 days ago
OriginDestinationTravel datesFlights from*
YVRKelownaAugust 4 to August 6CA $153
YVRPentictonSeptember 4 to September 6CA $162
YEGKelownaSeptember 22 to October 6CA $162
YYCKelownaSeptember 7 to September 11CA $176
YYJKelownaAugust 19 to August 19CA $229
YYJPentictonJuly 26 to July 29CA $266
YYCPentictonAugust 31 to September 1CA $287
YEGPentictonJuly 21 to July 22CA $290
YYZKelownaOctober 15 to October 22CA $402
SEAKelownaSeptember 29 to October 7CA $505
YYZPentictonOctober 8 to October 15CA $553
LAXPentictonOctober 1 to October 14CA $564
LAXKelownaAugust 17 to August 24CA $604
YQMKelownaSeptember 11 to September 19CA $688
PHLKelownaAugust 10 to August 17CA $1,111
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
YEGKelownaJuly 12 to July 15CA $200
YVRKelownaJuly 11 to July 16CA $272
YYCKelownaJuly 10 to July 12CA $358
YVRPentictonJuly 12 to July 21CA $413
YYJKelownaJuly 12 to July 15CA $483
YYJPentictonJuly 12 to July 16CA $585
YEGPentictonJuly 12 to July 26CA $748
YYCPentictonJuly 10 to July 13CA $897
YYZPentictonJuly 12 to August 17CA $916
SEAKelownaJuly 10 to July 13CA $1,017
YYZKelownaJuly 12 to July 20CA $1,018
YQMKelownaJuly 12 to July 28CA $1,088
LAXKelownaJuly 12 to July 16CA $1,293
SEAPentictonJuly 11 to July 18CA $1,535
LAXPentictonJuly 12 to July 15CA $1,594
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
The Royal Kelowna
4.0-star property

The Royal Kelowna

Oct 3 - Oct 6

3 night stay

Winnipeg (YWG) to Kelowna (YLW)

WestJet • Non-stop roundtrip • Coach
Price was CA $1,233, price is now CA $950 per person
CA $950
per person
found 18 hours ago
The White Pearl - Luxury Chalet W/mountain Views
3.5-star property

The White Pearl - Luxury Chalet W/mountain Views

Aug 21 - Aug 27

6 night stay

Calgary (YYC) to Kelowna (YLW)

Air Canada • Roundtrip • Coach
Price was CA $3,421, price is now CA $2,513 per person
CA $2,513
per person
found 8 hours ago
Western Star Chalet Ski In Out w Mtn View
4.0-star property

Western Star Chalet Ski In Out w Mtn View

Aug 21 - Aug 27

6 night stay

Calgary (YYC) to Kelowna (YLW)

Air Canada • Roundtrip • Coach
Price was CA $2,758, price is now CA $2,117 per person
CA $2,117
per person
found 8 hours 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 🏨

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 South Okanagan Events Centre and Okanagan Beach are located nearby.
7.6/10 Good! (1,219 reviews)
"We booked a room 6 months in advance, the room was available when we arrived and the room was clean except the bathroom had a soiled toilet seat, which someone came in to clean when we requested this. The AC unit only had the fan operational and it only had maximum fan speed available. We were double-charged ..."

Reviewed on Jul 7, 2026

Opens in a new windowSandman Hotel Penticton
Penticton Lakeside Resort and Conference Centre

Penticton Lakeside Resort and Conference Centre

3.5 out of 5
21 Lakeshore Dr W Penticton BC
Book a stay at this beach resort in Penticton. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Okanagan Beach and South Okanagan Events Centre are located nearby.
8.6/10 Excellent! (1,033 reviews)
"Be advised that the party on the deck can go loudly until 2:00am on Saturday night. When we checked out of our Lakeview room and mentioned the noise when asked how our stay was the Lady didn't even reply or comment. Everything else was great."

Reviewed on Jul 7, 2026

Opens in a new windowPenticton Lakeside Resort and Conference Centre
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 Osoyoos Lake and Nk'Mip Cellars are located nearby.
9.2/10 Wonderful! (1,480 reviews)
"The restaurant served delicious Mediterranean food. The outdoor pool is fantastic. Perfect temperature and great for swimming laps. The view from the room was great!!"

Reviewed on Jul 6, 2026

Opens in a new windowWalnut Beach Resort
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Days Inn & Conference Centre by Wyndham Penticton

Days Inn & Conference Centre by Wyndham Penticton

2.5 out of 5
152 Riverside Dr Penticton BC
Book a stay at this business-friendly hotel in Penticton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions South Okanagan Events Centre and Okanagan Beach are located nearby.
8.2/10 Very good! (1,560 reviews)
"Excellent"

Reviewed on Jul 6, 2026

Opens in a new windowDays Inn & Conference Centre by Wyndham Penticton
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 CA $142 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, September 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. CA $142 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 CA $142 and CA $1,594. 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.