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Cheap flights from Chicago to Kelowna from C$ 157

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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YLW
7 Mar — 14 Mar1
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 5 February 2026.

Fri 10/42:20 p.m.
ORD
-
YLW
1 stop6h 48m
WestJet
Fri 17/45:20 a.m.
YLW
-
ORD
1 stop6h 15m
WestJet
Deal found 1/2C$ 311
Fri 10/42:20 p.m.
ORD
-
YLW
1 stop6h 48m
Multiple Airlines
Fri 17/46:05 a.m.
YLW
-
ORD
2 stops33h 36m
Multiple Airlines
Deal found 4/2C$ 393
Tue 3/33:54 p.m.
ORD
-
YLW
1 stop7h 18m
Alaska Airlines
Wed 4/31:35 p.m.
YLW
-
ORD
1 stop8h 21m
Alaska Airlines
Deal found 2/2C$ 460
Wed 4/36:02 p.m.
ORD
-
YLW
2 stops26h 03m
Multiple Airlines
Wed 11/32:55 p.m.
YLW
-
ORD
1 stop11h 54m
Multiple Airlines
Deal found 2/2C$ 517
Tue 3/38:00 a.m.
ORD
-
YLW
2 stops13h 59m
Air Canada
Wed 4/35:20 a.m.
YLW
-
ORD
1 stop7h 21m
Air Canada
Deal found 1/2C$ 548
Sun 1/33:54 p.m.
ORD
-
YLW
1 stop7h 18m
Multiple Airlines
Fri 20/35:20 a.m.
YLW
-
ORD
1 stop6h 15m
Multiple Airlines
Deal found 3/2C$ 550
Wed 4/33:35 p.m.
ORD
-
YLW
1 stop9h 38m
Air Canada
Wed 11/38:30 p.m.
YLW
-
ORD
1 stop16h 11m
Air Canada
Deal found 2/2C$ 561
Wed 11/29:53 a.m.
MDW
-
YLW
2 stops25h 36m
WestJet
Sun 22/26:35 p.m.
YLW
-
MDW
2 stops13h 19m
WestJet
Deal found 2/2C$ 1,293
Thu 12/39:30 a.m.
MDW
-
YLW
2 stops11h 02m
WestJet
Tue 17/37:55 p.m.
YLW
-
MDW
2 stops12h 01m
WestJet
Deal found 4/2C$ 1,320
Thu 26/27:20 p.m.
MDW
-
YLW
2 stops24h 41m
WestJet
Sun 1/34:00 p.m.
YLW
-
MDW
2 stops24h 40m
WestJet
Deal found 3/2C$ 1,338
Wed 11/210:46 a.m.
MDW
-
YLW
2 stops13h 02m
WestJet
Sun 15/27:35 p.m.
YLW
-
MDW
2 stops12h 19m
WestJet
Deal found 1/2C$ 1,344
Mon 2/39:50 a.m.
MDW
-
YLW
2 stops48h 10m
WestJet
Wed 4/310:10 a.m.
YLW
-
MDW
2 stops30h 30m
WestJet
Deal found 3/2C$ 1,430

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 5 February 2026.

Round-trip from

C$ 311

One-way from

C$ 157

Popular in

October

Cheapest in

July

Average price

C$ 724
WestJet
  • WestJet
  • 10/4-17/4
  • 2 total stops
  • 13h 03m total
  • Chicago to Kelowna
Search Deals
WestJet
  • WestJet
  • 9/6
  • 1 total stop
  • 19h 45m total
  • Chicago to Kelowna
Search Deals
Highest demand for flights based on searches. 26% potential increase in price (C$ 368 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease (C$ 109 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 5 February 2026.
Use the filters below to find and compare flights from Chicago to Kelowna that are best for you.

Fly from

Chicago

Fly to

Kelowna

Route

Depart

Return

Price

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Fri 10/4

2:20 p.m.-7:08 p.m.

1 stop6h 48m

Kelowna

Fri 17/4

5:20 a.m.-1:35 p.m.

1 stop6h 15m

C$ 311

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Fri 10/4

2:20 p.m.-7:08 p.m.

1 stop6h 48m

Kelowna

Fri 17/4

6:05 a.m.-5:41 p.m.

2 stops33h 36m

C$ 393

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 3/3

3:54 p.m.-9:12 p.m.

1 stop7h 18m

Kelowna

Wed 4/3

1:35 p.m.-11:56 p.m.

1 stop8h 21m

C$ 460

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 3/3

8:00 a.m.-7:59 p.m.

2 stops13h 59m

Kelowna

Wed 4/3

5:20 a.m.-2:41 p.m.

1 stop7h 21m

C$ 548

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sun 1/3

3:54 p.m.-9:12 p.m.

1 stop7h 18m

Kelowna

Fri 20/3

5:20 a.m.-1:35 p.m.

1 stop6h 15m

C$ 550

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Wed 4/3

3:35 p.m.-11:13 p.m.

1 stop9h 38m

Kelowna

Wed 11/3

8:30 p.m.-2:41 p.m.

1 stop16h 11m

C$ 561

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 12/3

9:30 a.m.-6:32 p.m.

2 stops11h 02m

Kelowna

Tue 17/3

7:55 p.m.-9:56 a.m.

2 stops12h 01m

C$ 1,320

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 26/2

7:20 p.m.-6:01 p.m.

2 stops24h 41m

Kelowna

Sun 1/3

4:00 p.m.-6:40 p.m.

2 stops24h 40m

C$ 1,338

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 2/3

9:50 a.m.-8:00 a.m.

2 stops48h 10m

Kelowna

Wed 4/3

10:10 a.m.-6:40 p.m.

2 stops30h 30m

C$ 1,430

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 20/2

9:50 a.m.-6:26 p.m.

2 stops10h 36m

Kelowna

Sun 22/2

6:35 p.m.-9:54 a.m.

2 stops13h 19m

C$ 1,476

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 30 results
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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

How much does it cost to fly round-trip from Chicago to Kelowna?

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 Alaska Airlines can get you from Chicago to Kelowna in just under 6h 48m. Your travel time can differ by up to 30m. 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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Why should you use Cheapflights to find cheap flight tickets from Chicago to Kelowna?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago to Kelowna.

Can Cheapflights find flights from Chicago to Kelowna with no change fees?

Yes, we can. To see specific flights from Chicago to Kelowna with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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