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Cheap flights from Chicago to Kelowna from C$ 199

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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YLW
22 Apr — 29 Apr1
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 23 March 2026.

Sun 3/55:30 p.m.
ORD
-
YLW
1 stop8h 20m
WestJet
Sun 10/56:05 a.m.
YLW
-
ORD
1 stop8h 35m
WestJet
Deal found 19/3C$ 436
Sun 26/45:30 p.m.
ORD
-
YLW
1 stop6h 35m
WestJet
Thu 30/47:50 a.m.
YLW
-
ORD
1 stop6h 50m
WestJet
Deal found 21/3C$ 443
Sat 25/42:00 p.m.
ORD
-
YLW
1 stop10h 11m
Air Canada
Wed 29/45:20 a.m.
YLW
-
ORD
1 stop7h 25m
Air Canada
Deal found 21/3C$ 469
Thu 14/55:30 p.m.
ORD
-
YLW
1 stop8h 20m
WestJet
Mon 18/58:15 p.m.
YLW
-
ORD
1 stop18h 25m
WestJet
Deal found 22/3C$ 475
Mon 4/56:00 a.m.
ORD
-
YLW
1 stop10h 47m
Multiple Airlines
Thu 7/57:50 a.m.
YLW
-
ORD
1 stop6h 50m
Multiple Airlines
Deal found 19/3C$ 476
Sat 25/44:15 p.m.
ORD
-
YLW
1 stop7h 56m
Air Canada
Tue 28/411:15 p.m.
YLW
-
ORD
1 stop7h 55m
Air Canada
Deal found 19/3C$ 480
Tue 5/58:48 p.m.
ORD
-
YLW
1 stop19h 59m
Alaska Airlines
Tue 12/53:37 p.m.
YLW
-
ORD
1 stop12h 43m
Alaska Airlines
Deal found 21/3C$ 536
Fri 1/51:24 p.m.
MDW
-
YLW
2 stops10h 41m
Delta
Mon 4/56:05 a.m.
YLW
-
MDW
2 stops9h 53m
Delta
Deal found 22/3C$ 722
Wed 8/411:00 a.m.
MDW
-
YLW
2 stops12h 48m
Multiple Airlines
Thu 9/44:00 p.m.
YLW
-
MDW
3 stops21h 20m
Multiple Airlines
Deal found 18/3C$ 877
Wed 29/411:00 a.m.
MDW
-
YLW
3 stops14h 50m
Multiple Airlines
Mon 4/512:05 p.m.
YLW
-
MDW
3 stops19h 40m
Multiple Airlines
Deal found 22/3C$ 1,000
Mon 29/61:00 p.m.
MDW
-
YLW
2 stops12h 50m
Delta
Fri 3/76:05 a.m.
YLW
-
MDW
2 stops10h 26m
Delta
Deal found 19/3C$ 1,054
Thu 21/51:22 p.m.
MDW
-
YLW
3 stops32h 58m
Multiple Airlines
Sun 24/512:40 p.m.
YLW
-
MDW
2 stops19h 00m
Multiple Airlines
Deal found 19/3C$ 1,124

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 23 March 2026.

Round-trip from

C$ 436

One-way from

C$ 199

Popular in

October

Cheapest in

March

Average price

C$ 230
WestJet
  • WestJet
  • 3/5-10/5
  • 2 total stops
  • 16h 55m total
  • Chicago to Kelowna
Search Deals
Air Canada
  • Air Canada
  • 9/4
  • 1 total stop
  • 9h 13m total
  • Chicago to Kelowna
Search Deals
Highest demand for flights based on searches. 28% potential increase in price (C$ 403 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 14% potential price decrease (C$ 126 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 23 March 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

Sat 25/4

6:25 a.m.-5:48 p.m.

2 stops13h 23m

Kelowna

Tue 28/4

10:25 a.m.-8:15 p.m.

1 stop7h 50m

C$ 573

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Thu 14/5

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

1 stop8h 20m

Kelowna

Mon 18/5

4:45 p.m.-4:40 p.m.

2 stops21h 55m

C$ 593

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sat 25/4

6:25 a.m.-5:48 p.m.

2 stops13h 23m

Kelowna

Wed 29/4

10:25 a.m.-12:29 a.m.

2 stops12h 04m

C$ 595

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sat 25/4

8:00 a.m.-2:47 p.m.

1 stop8h 47m

Kelowna

Wed 29/4

6:30 p.m.-10:23 a.m.

2 stops13h 53m

C$ 612

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sun 3/5

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

1 stop8h 20m

Kelowna

Sun 10/5

3:15 p.m.-10:46 a.m.

3 stops17h 31m

C$ 617

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Thu 14/5

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

1 stop8h 20m

Kelowna

Mon 18/5

3:36 p.m.-6:20 a.m.

1 stop12h 44m

C$ 665
Quickest round-trip

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Thu 21/5

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

1 stop8h 20m

Kelowna

Sun 24/5

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

1 stop6h 50m

C$ 668

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 5/5

1:24 p.m.-10:05 p.m.

2 stops10h 41m

Kelowna

Tue 12/5

6:05 a.m.-6:33 p.m.

2 stops10h 28m

C$ 722

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 1/5

1:24 p.m.-10:05 p.m.

2 stops10h 41m

Kelowna

Mon 4/5

6:05 a.m.-5:58 p.m.

2 stops9h 53m

C$ 722

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Mon 4/5

1:36 p.m.-10:05 p.m.

2 stops10h 29m

Kelowna

Mon 11/5

6:05 a.m.-8:14 p.m.

2 stops12h 09m

C$ 722

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/3

Showing 1-10 of 35 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?

    Air Canada, WestJet, and United Airlines can get you from Chicago to Kelowna in just under 8h 20m. Your travel time can differ by up to 5h 03m. 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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