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Cheap flights from Chicago to Kelowna from C$ 237

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YLW
9 Sep — 16 Sep1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Chicago to Kelowna

Enter your travel dates to find the best prices.

Cheapest flights from Chicago to Kelowna
Explore the most affordable flight options available from Chicago to Kelowna. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 10 August 2026.

Sun 13/95:30 p.m. -
1 stop8h 20m
Sun 20/97:50 a.m. -
1 stop6h 50m
Deal found 9/8C$ 479
Thu 24/95:30 p.m. -
1 stop8h 20m
Mon 28/96:30 p.m. -
1 stop20h 10m
Deal found 7/8C$ 489
Thu 1/105:30 p.m. -
1 stop8h 20m
Mon 5/107:50 a.m. -
1 stop6h 50m
Deal found 9/8C$ 491
Thu 24/95:30 p.m. -
1 stop8h 20m
Thu 1/106:30 p.m. -
1 stop20h 10m
Deal found 10/8C$ 496
Thu 17/95:30 p.m. -
1 stop8h 20m
Thu 24/98:15 p.m. -
1 stop18h 25m
Deal found 8/8C$ 521
Thu 24/911:45 a.m. -
1 stop12h 07m
Mon 28/97:50 p.m. -
2 stops13h 10m
Deal found 7/8C$ 666
Thu 24/911:45 a.m. -
1 stop12h 07m
Mon 28/910:50 p.m. -
1 stop13h 45m
Deal found 7/8C$ 694
Sun 30/810:20 a.m. -
1 stop13h 32m
Sat 5/96:35 p.m. -
2 stops18h 00m
Deal found 6/8C$ 833
Mon 31/810:25 a.m. -
2 stops13h 40m
Sat 5/92:30 p.m. -
2 stops18h 30m
Deal found 6/8C$ 847
Fri 28/810:25 a.m. -
1 stop13h 27m
Sat 5/96:35 p.m. -
2 stops18h 00m
Deal found 6/8C$ 964
Sun 13/911:45 a.m. -
3 stops21h 15m
Sun 20/912:50 p.m. -
2 stops20h 10m
Deal found 9/8C$ 988

Find flight deals from Chicago to Kelowna

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Kelowna (YLW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 10 August 2026.

Round-trip from

C$ 479

One-way from

C$ 237
WestJet
  • WestJet
  • 13/9-20/9
  • 2 total stops
  • 15h 10m total
  • Chicago to Kelowna
Search Deals
WestJet
  • WestJet
  • 1/10
  • 1 total stop
  • 16h 50m total
  • Chicago to Kelowna
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Kelowna that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 10 August 2026.
Use the filters below to find and compare flights from Chicago to Kelowna that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKelowna

ORD Chicago O'Hare Intl - YLW Kelowna

ORDYLW

Chicago O'Hare Intl

Thu 24/9

5:30 p.m.-11:50 p.m.

1 stop8h 20m

Kelowna

Mon 28/9

8:15 p.m.-4:40 p.m.

1 stop18h 25m

C$ 489

ChicagoKelowna

ORD Chicago O'Hare Intl - YLW Kelowna

ORDYLW

Chicago O'Hare Intl

Thu 17/9

5:30 p.m.-11:50 p.m.

1 stop8h 20m

Kelowna

Thu 24/9

8:15 p.m.-4:40 p.m.

1 stop18h 25m

C$ 521
Quickest round-trip

ChicagoKelowna

ORD Chicago O'Hare Intl - YLW Kelowna

ORDYLW

Chicago O'Hare Intl

Sun 13/9

5:30 p.m.-11:50 p.m.

1 stop8h 20m

Kelowna

Sun 20/9

7:50 a.m.-4:40 p.m.

1 stop6h 50m

C$ 545

ChicagoKelowna

ORD Chicago O'Hare Intl - YLW Kelowna

ORDYLW

Chicago O'Hare Intl

Thu 24/9

5:30 p.m.-11:50 p.m.

1 stop8h 20m

Kelowna

Thu 1/10

7:50 p.m.-4:40 p.m.

2 stops18h 50m

C$ 552

ChicagoKelowna

ORD Chicago O'Hare Intl - YLW Kelowna

ORDYLW

Chicago O'Hare Intl

Sun 13/9

5:30 p.m.-11:50 p.m.

1 stop8h 20m

Kelowna

Sun 20/9

8:15 p.m.-12:23 a.m.

2 stops26h 08m

C$ 577

ChicagoKelowna

ORD Chicago O'Hare Intl - YLW Kelowna

ORDYLW

Chicago O'Hare Intl

Thu 24/9

3:40 p.m.-11:27 p.m.

1 stop9h 47m

Kelowna

Mon 28/9

10:50 p.m.-9:00 a.m.

1 stop8h 10m

C$ 620

ChicagoKelowna

ORD Chicago O'Hare Intl - YLW Kelowna

ORDYLW

Chicago O'Hare Intl

Sun 6/9

5:30 p.m.-11:50 p.m.

1 stop8h 20m

Kelowna

Sun 13/9

8:15 p.m.-12:23 a.m.

2 stops26h 08m

C$ 627

ChicagoKelowna

ORD Chicago O'Hare Intl - YLW Kelowna

ORDYLW

Chicago O'Hare Intl

Thu 24/9

5:30 p.m.-10:55 a.m.

2 stops19h 25m

Kelowna

Mon 28/9

7:50 p.m.-4:40 p.m.

2 stops18h 50m

C$ 673

ChicagoKelowna

MDW Chicago Midway - YLW Kelowna

MDWYLW

Chicago Midway

Thu 24/9

11:45 a.m.-9:52 p.m.

1 stop12h 07m

Kelowna

Mon 28/9

10:50 p.m.-2:35 p.m.

1 stop13h 45m

C$ 694

ChicagoKelowna

MDW Chicago Midway - YLW Kelowna

MDWYLW

Chicago Midway

Sun 30/8

10:20 a.m.-9:52 p.m.

1 stop13h 32m

Kelowna

Sat 5/9

6:35 p.m.-2:35 p.m.

2 stops18h 00m

C$ 833

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/8

Showing 1-10 of 24 resultsSorted by cheapest first
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Best time to book a flight from Chicago to Kelowna

Have a flexible travel schedule? Discover the best time to fly to Kelowna from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Kelowna

No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Kelowna. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Kelowna from Chicago?

    Located just 11.2 km from the city centre, Kelowna is the airport most travellers will use when flying to Kelowna from Chicago. Booking flights from Chicago to Kelowna (YLW) should be relatively easy as there are 0 daily inbound flights from Chicago from 0 different airlines.

  • How long is the flight from Chicago to Kelowna?

    WestJet and Porter Airlines can get you from Chicago to Kelowna in just under 8h 20m. Your travel time can differ by up to 3h 47m. The distance from Chicago to Kelowna is about 2565 km. Both multi-stop and direct flights can be found to your destination and back.

  • Can I find deals for flights from Chicago to Kelowna that include hotel bookings?

    Yes. In addition to deals on Chicago to Kelowna flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Kelowna?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Kelowna.

  • Can I find deals for business class flights from Chicago to Kelowna?

    Yes. Cheapflights offers flight deals from Chicago to Kelowna by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Travelling to a place near Kelowna?

Book flights to Kelowna if you plan to visit one of these locations
Salmon Arm
West Kelowna
Big White

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