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Cheap flights from Chicago to Kelowna from C$ 127

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 16/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YLW
15 Oct — 22 Oct1
1 adult
1 adult, Economy

Cheap 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 15 September 2025.

Round-trip from

C$ 256

One-way from

C$ 127

Popular in

December

Cheapest in

March

Average price

C$ 500
WestJet
  • WestJet
  • 27/2-2/3
  • 2 total stops
  • 13h 03m total
  • Chicago to Kelowna
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WestJet
  • WestJet
  • 16/10
  • 1 total stop
  • 8h 09m total
  • Chicago to Kelowna
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Highest demand for flights based on searches. 15% potential increase in price (C$ 170 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease (C$ 48 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Kelowna

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 15 September 2025.

Mon 15/95:30 p.m.ORD - YLW
2 stops26h 17mMultiple Airlines
Fri 19/98:45 p.m.YLW - ORD
1 stop13h 54mMultiple Airlines
Deal found 13/9C$ 627
Tue 16/95:30 p.m.ORD - YLW
2 stops17h 52mMultiple Airlines
Fri 19/98:45 p.m.YLW - ORD
1 stop13h 54mMultiple Airlines
Deal found 13/9C$ 638
Mon 15/95:30 p.m.ORD - YLW
2 stops22h 02mWestJet
Fri 19/98:15 p.m.YLW - ORD
2 stops14h 24mWestJet
Deal found 13/9C$ 934
Mon 15/95:30 p.m.ORD - YLW
2 stops26h 17mMultiple Airlines
Sat 20/92:47 p.m.YLW - ORD
1 stop7h 16mMultiple Airlines
Deal found 13/9C$ 949
Tue 16/95:30 p.m.ORD - YLW
2 stops17h 52mMultiple Airlines
Sat 20/92:47 p.m.YLW - ORD
1 stop7h 16mMultiple Airlines
Deal found 13/9C$ 960
Sun 28/99:20 a.m.MDW - YLW
2 stops27h 40mMultiple Airlines
Wed 1/1011:55 a.m.YLW - MDW
2 stops27h 40mMultiple Airlines
Deal found 15/9C$ 973
Sun 14/98:01 p.m.ORD - YLW
2 stops40h 54mMultiple Airlines
Fri 19/98:45 p.m.YLW - ORD
1 stop13h 54mMultiple Airlines
Deal found 14/9C$ 1,002
Tue 16/95:30 p.m.ORD - YLW
2 stops22h 02mWestJet
Sat 20/910:00 a.m.YLW - ORD
2 stops9h 30mWestJet
Deal found 13/9C$ 1,031
Mon 15/95:30 p.m.ORD - YLW
2 stops26h 17mMultiple Airlines
Sun 21/92:47 p.m.YLW - ORD
1 stop7h 16mMultiple Airlines
Deal found 13/9C$ 1,130
Mon 15/95:30 p.m.ORD - YLW
2 stops17h 52mWestJet
Sun 21/98:15 p.m.YLW - ORD
2 stops11h 55mWestJet
Deal found 13/9C$ 1,133
Tue 16/95:30 p.m.ORD - YLW
2 stops17h 52mMultiple Airlines
Sun 21/92:47 p.m.YLW - ORD
1 stop7h 16mMultiple Airlines
Deal found 13/9C$ 1,141

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 15 September 2025.
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 27/2

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

1 stop6h 48m

Kelowna

Mon 2/3

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

1 stop6h 15m

C$ 256

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sun 25/1

3:40 p.m.-10:58 p.m.

1 stop9h 18m

Kelowna

Sat 31/1

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

1 stop7h 21m

C$ 290

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sun 25/1

6:47 a.m.-10:58 p.m.

2 stops18h 11m

Kelowna

Sat 31/1

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

1 stop7h 21m

C$ 408

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Fri 27/2

9:10 p.m.-8:09 p.m.

2 stops24h 59m

Kelowna

Mon 2/3

10:25 a.m.-6:21 a.m.

2 stops17h 56m

C$ 434

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sun 4/1

3:40 p.m.-10:58 p.m.

1 stop9h 18m

Kelowna

Sun 11/1

8:55 p.m.-2:41 p.m.

1 stop15h 46m

C$ 561

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sun 4/1

3:40 p.m.-10:58 p.m.

1 stop9h 18m

Kelowna

Sun 11/1

8:55 p.m.-9:32 p.m.

2 stops22h 37m

C$ 602

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 28/9

7:15 p.m.-9:49 p.m.

3 stops28h 34m

Kelowna

Wed 1/10

11:55 a.m.-5:35 p.m.

2 stops27h 40m

C$ 973

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 25/1

2:00 p.m.-11:55 p.m.

2 stops11h 55m

Kelowna

Sat 31/1

7:55 p.m.-12:01 p.m.

2 stops14h 06m

C$ 1,126

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Thu 16/10

5:30 p.m.-11:39 p.m.

1 stop8h 09m

C$ 127

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sat 27/9

6:15 a.m.-1:21 p.m.

2 stops33h 06m

C$ 198

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/9

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

What is the cheapest month to book a flight from Chicago to Kelowna?

Currently, October is the cheapest month in which you can book a flight from Chicago to Kelowna (average of C$ 137). Flying from Chicago to Kelowna in March is currently the most expensive (average of C$ 238). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 United Airlines can get you from Chicago to Kelowna in just under 6h 48m. Your travel time can differ by up to 11h 23m. 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.

  • What is the cheapest month to book a flight from Chicago to Kelowna?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Kelowna (average of C$ 137). Flying from Chicago to Kelowna in March is currently the most expensive (average of C$ 238). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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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