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Cheap flights from Chicago to Kelowna from C$ 257

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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YLW
27 Jul — 3 Aug1
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 27 June 2026.

Thu 24/95:30 p.m.
ORD
-
YLW
1 stop8h 20m
WestJet
Mon 28/96:05 a.m.
YLW
-
ORD
1 stop8h 35m
WestJet
Deal found 22/6C$ 524
Wed 12/85:30 p.m.
ORD
-
YLW
1 stop6h 35m
WestJet
Tue 22/96:05 a.m.
YLW
-
ORD
1 stop8h 35m
WestJet
Deal found 26/6C$ 531
Thu 1/105:30 p.m.
ORD
-
YLW
1 stop6h 35m
WestJet
Mon 5/107:50 a.m.
YLW
-
ORD
1 stop6h 50m
WestJet
Deal found 25/6C$ 536
Fri 4/97:00 a.m.
ORD
-
YLW
2 stops14h 00m
Multiple Airlines
Sun 6/97:50 a.m.
YLW
-
ORD
1 stop6h 50m
Multiple Airlines
Deal found 22/6C$ 592
Mon 28/93:40 p.m.
ORD
-
YLW
1 stop9h 47m
Air Canada
Thu 1/105:25 a.m.
YLW
-
ORD
1 stop7h 18m
Air Canada
Deal found 22/6C$ 602
Thu 10/95:30 p.m.
ORD
-
YLW
1 stop6h 35m
WestJet
Mon 14/96:05 a.m.
YLW
-
ORD
1 stop8h 35m
WestJet
Deal found 25/6C$ 612
Thu 1/103:40 p.m.
ORD
-
YLW
1 stop9h 32m
Air Canada
Mon 5/107:25 p.m.
YLW
-
ORD
2 stops11h 35m
Air Canada
Deal found 22/6C$ 616
Thu 13/810:25 a.m.
MDW
-
YLW
1 stop13h 27m
Porter Airlines
Mon 17/810:50 p.m.
YLW
-
MDW
1 stop13h 45m
Porter Airlines
Deal found 23/6C$ 890
Thu 13/810:20 a.m.
MDW
-
YLW
1 stop13h 32m
Multiple Airlines
Mon 17/88:15 p.m.
YLW
-
MDW
2 stops16h 20m
Multiple Airlines
Deal found 22/6C$ 900
Thu 24/91:19 p.m.
MDW
-
YLW
2 stops10h 46m
Delta
Mon 28/98:15 p.m.
YLW
-
MDW
2 stops13h 40m
Delta
Deal found 22/6C$ 1,009
Mon 10/89:24 a.m.
MDW
-
YLW
3 stops27h 51m
WestJet
Mon 17/812:05 p.m.
YLW
-
MDW
3 stops22h 34m
WestJet
Deal found 26/6C$ 1,154
Fri 4/91:25 p.m.
MDW
-
YLW
3 stops31h 05m
WestJet
Sun 6/98:15 p.m.
YLW
-
MDW
3 stops14h 24m
WestJet
Deal found 22/6C$ 1,220

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 27 June 2026.

Round-trip from

C$ 524

One-way from

C$ 257
WestJet
  • WestJet
  • 24/9-28/9
  • 2 total stops
  • 16h 55m total
  • Chicago to Kelowna
Search Deals
12/8
  • 12/8
  • 3 total stops
  • 28h 17m 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 27 June 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 - YLW

ORDYLW

Chicago O'Hare Intl

Thu 24/9

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

1 stop8h 20m

Kelowna

Mon 28/9

6:05 a.m.-4:40 p.m.

1 stop8h 35m

C$ 524
Quickest round-trip

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Wed 12/8

5:30 p.m.-10:05 p.m.

1 stop6h 35m

Kelowna

Tue 22/9

6:05 a.m.-4:40 p.m.

1 stop8h 35m

C$ 531

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Thu 10/9

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

1 stop9h 47m

Kelowna

Mon 14/9

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

1 stop8h 10m

C$ 629

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Mon 20/7

5:30 p.m.-10:05 p.m.

1 stop6h 35m

Kelowna

Wed 22/7

6:05 a.m.-4:40 p.m.

1 stop8h 35m

C$ 633

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Thu 6/8

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

1 stop8h 20m

Kelowna

Mon 10/8

10:55 a.m.-4:40 p.m.

1 stop27h 45m

C$ 644

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Fri 4/9

1:59 p.m.-11:50 p.m.

2 stops11h 51m

Kelowna

Sun 6/9

6:05 a.m.-4:40 p.m.

1 stop8h 35m

C$ 724

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Mon 28/9

5:00 a.m.-12:17 p.m.

2 stops9h 17m

Kelowna

Thu 1/10

5:25 a.m.-2:43 p.m.

1 stop7h 18m

C$ 732

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Thu 13/8

5:30 p.m.-7:25 p.m.

1 stop27h 55m

Kelowna

Mon 17/8

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

1 stop18h 25m

C$ 744

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 13/8

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

1 stop13h 32m

Kelowna

Mon 17/8

8:15 p.m.-2:35 p.m.

2 stops16h 20m

C$ 900

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 13/8

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

1 stop13h 32m

Kelowna

Mon 17/8

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

1 stop13h 45m

C$ 907

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/6

Showing 1-10 of 26 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, Air Canada, and Porter Airlines can get you from Chicago to Kelowna in just under 8h 20m. Your travel time can differ by up to 5h 12m. 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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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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Not ready to book yet? You can track prices for flights from Chicago to Kelowna on Cheapflights with our Price Alert feature and get notified when better prices are available.

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