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Cheap flights from Chicago to Kelowna from C$ 267

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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YLW
10 Jun — 17 Jun1
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 11 May 2026.

Thu 13/85:30 p.m.
ORD
-
YLW
1 stop6h 35m
WestJet
Mon 17/87:50 a.m.
YLW
-
ORD
1 stop6h 50m
WestJet
Deal found 9/5C$ 613
Sat 6/69:55 a.m.
ORD
-
YLW
1 stop13h 56m
Air Canada
Sat 13/610:50 p.m.
YLW
-
ORD
1 stop8h 10m
Air Canada
Deal found 8/5C$ 645
Tue 11/85:30 p.m.
ORD
-
YLW
2 stops18h 15m
WestJet
Sun 16/86:35 p.m.
YLW
-
ORD
2 stops20h 05m
WestJet
Deal found 10/5C$ 659
Sat 26/93:40 p.m.
ORD
-
YLW
1 stop9h 32m
Air Canada
Tue 29/911:30 p.m.
YLW
-
ORD
1 stop7h 30m
Air Canada
Deal found 6/5C$ 677
Tue 20/102:15 p.m.
ORD
-
YLW
2 stops10h 57m
Air Canada
Sat 24/105:25 a.m.
YLW
-
ORD
1 stop7h 23m
Air Canada
Deal found 9/5C$ 684
Sat 30/56:00 a.m.
ORD
-
YLW
1 stop10h 46m
Alaska Airlines
Tue 9/63:36 p.m.
YLW
-
ORD
2 stops11h 24m
Alaska Airlines
Deal found 8/5C$ 686
Tue 14/76:00 a.m.
MDW
-
YLW
2 stops40h 20m
Multiple Airlines
Tue 21/711:45 a.m.
YLW
-
MDW
1 stop19h 55m
Multiple Airlines
Deal found 10/5C$ 838
Tue 14/73:20 p.m.
MDW
-
YLW
1 stop21h 27m
Porter Airlines
Tue 21/711:45 a.m.
YLW
-
MDW
1 stop19h 55m
Porter Airlines
Deal found 10/5C$ 964
Tue 14/71:18 p.m.
MDW
-
YLW
3 stops23h 57m
WestJet
Tue 21/75:05 a.m.
YLW
-
MDW
3 stops11h 20m
WestJet
Deal found 10/5C$ 1,310
Sun 21/69:17 a.m.
MDW
-
YLW
3 stops12h 48m
Multiple Airlines
Sun 28/612:50 p.m.
YLW
-
MDW
2 stops18h 50m
Multiple Airlines
Deal found 7/5C$ 1,342
Fri 19/69:54 a.m.
MDW
-
YLW
2 stops11h 31m
WestJet
Mon 22/65:05 a.m.
YLW
-
MDW
2 stops11h 13m
WestJet
Deal found 7/5C$ 1,481
Mon 29/61:26 p.m.
MDW
-
YLW
2 stops10h 39m
WestJet
Sun 5/76:00 a.m.
YLW
-
MDW
2 stops10h 18m
WestJet
Deal found 10/5C$ 1,486

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 11 May 2026.

Round-trip from

C$ 613

One-way from

C$ 267
WestJet
  • WestJet
  • 13/8-17/8
  • 2 total stops
  • 13h 25m total
  • Chicago to Kelowna
Search Deals
WestJet
  • WestJet
  • 5/6
  • 1 total stop
  • 6h 35m 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 11 May 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

Tue 11/8

5:30 p.m.-9:45 a.m.

2 stops18h 15m

Kelowna

Sun 16/8

6:35 p.m.-4:40 p.m.

2 stops20h 05m

C$ 659
Quickest round-trip

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 20/10

3:40 p.m.-11:12 p.m.

1 stop9h 32m

Kelowna

Sat 24/10

5:25 a.m.-2:48 p.m.

1 stop7h 23m

C$ 665

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 14/7

6:00 a.m.-8:20 p.m.

2 stops40h 20m

Kelowna

Tue 21/7

11:45 a.m.-9:40 a.m.

1 stop19h 55m

C$ 838

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 21/6

9:17 a.m.-8:05 p.m.

3 stops12h 48m

Kelowna

Sun 28/6

12:50 p.m.-9:40 a.m.

2 stops18h 50m

C$ 1,342

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 11/8

1:27 p.m.-11:50 p.m.

2 stops12h 23m

Kelowna

Sun 16/8

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

2 stops10h 28m

C$ 1,488

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 13/8

1:27 p.m.-10:05 p.m.

2 stops10h 38m

Kelowna

Mon 17/8

6:00 a.m.-6:01 p.m.

2 stops10h 01m

C$ 1,519

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 10/8

12:46 p.m.-11:50 p.m.

2 stops13h 04m

Kelowna

Tue 18/8

6:00 a.m.-6:01 p.m.

2 stops10h 01m

C$ 1,519

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sat 26/9

2:00 p.m.-11:50 p.m.

2 stops11h 50m

Kelowna

Tue 29/9

9:10 a.m.-6:05 p.m.

2 stops30h 55m

C$ 1,649

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 20/10

9:30 a.m.-10:05 p.m.

2 stops14h 35m

Kelowna

Sat 24/10

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

2 stops22h 42m

C$ 1,666
Cheapest one-way
Quickest one-way

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Fri 5/6

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

1 stop6h 35m

C$ 267

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/5

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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 Delta can get you from Chicago to Kelowna in just under 12h 23m. Your travel time can differ by up to 5h 52m. The distance from Chicago to Kelowna is about 2586 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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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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