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Kelowna

$92+ Cheap flights from Chicago (CHI) to Kelowna (YLW)

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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YLW
out 15 — out 221
qua 10/15
qua 10/22
1 adult, Economy
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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 setembro 15, 2025.

Round-trip from

$185
(oojo)

One-way from

$92
(Expedia)

Popular in

December

Cheapest in

March

Average price

$362
From Chicago (CHI) to Kelowna
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One-way flight from Chicago (CHI) to Kelowna
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Highest demand for flights based on searches. 15% potential increase in price ($90 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($25 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 setembro 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 9/155:30 pmORD - YLW
2 stops26h 17mMultiple Airlines
sex 9/198:45 pmYLW - ORD
1 stop13h 54mMultiple Airlines
Deal found 9/13$454
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 9/165:30 pmORD - YLW
2 stops17h 52mMultiple Airlines
sex 9/198:45 pmYLW - ORD
1 stop13h 54mMultiple Airlines
Deal found 9/13$462
This FlightHub deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 9/155:30 pmORD - YLW
2 stops22h 02mWestJet
sex 9/198:15 pmYLW - ORD
2 stops14h 24mWestJet
Deal found 9/13$676
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 9/155:30 pmORD - YLW
2 stops26h 17mMultiple Airlines
sáb 9/202:47 pmYLW - ORD
1 stop7h 16mMultiple Airlines
Deal found 9/13$687
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 9/165:30 pmORD - YLW
2 stops17h 52mMultiple Airlines
sáb 9/202:47 pmYLW - ORD
1 stop7h 16mMultiple Airlines
Deal found 9/13$695
This Mytrip deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 9/287:15 pmMDW - YLW
3 stops28h 34mMultiple Airlines
qua 10/111:55 amYLW - MDW
2 stops27h 40mMultiple Airlines
Deal found 9/15$704
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 9/148:01 pmORD - YLW
2 stops40h 54mMultiple Airlines
sex 9/198:45 pmYLW - ORD
1 stop13h 54mMultiple Airlines
Deal found 9/14$725
This FlightHub deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 9/165:30 pmORD - YLW
2 stops22h 02mWestJet
sáb 9/2010:00 amYLW - ORD
2 stops9h 30mWestJet
Deal found 9/13$746
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 9/155:30 pmORD - YLW
2 stops26h 17mMultiple Airlines
dom 9/212:47 pmYLW - ORD
1 stop7h 16mMultiple Airlines
Deal found 9/13$818
This FlightHub deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 9/155:30 pmORD - YLW
2 stops17h 52mWestJet
dom 9/218:15 pmYLW - ORD
2 stops11h 55mWestJet
Deal found 9/13$820
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 9/165:30 pmORD - YLW
2 stops17h 52mMultiple Airlines
dom 9/212:47 pmYLW - ORD
1 stop7h 16mMultiple Airlines
Deal found 9/13$826

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 2,558,603 searches. Data last updated setembro 15, 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

sex 2/27

2:20 pm-7:08 pm

1 stop6h 48m

Kelowna

seg 3/2

5:20 am-1:35 pm

1 stop6h 15m

$185

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

dom 1/25

3:40 pm-10:58 pm

1 stop9h 18m

Kelowna

sáb 1/31

5:20 am-2:41 pm

1 stop7h 21m

$210

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

dom 1/25

6:47 am-10:58 pm

2 stops18h 11m

Kelowna

sáb 1/31

5:20 am-2:41 pm

1 stop7h 21m

$295

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

sex 2/27

9:10 pm-8:09 pm

2 stops24h 59m

Kelowna

seg 3/2

10:25 am-6:21 am

2 stops17h 56m

$314

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

dom 1/4

3:40 pm-10:58 pm

1 stop9h 18m

Kelowna

dom 1/11

8:55 pm-2:41 pm

1 stop15h 46m

$406

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

dom 1/4

3:40 pm-10:58 pm

1 stop9h 18m

Kelowna

dom 1/11

8:55 pm-9:32 pm

2 stops22h 37m

$436

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

dom 9/28

7:15 pm-9:49 pm

3 stops28h 34m

Kelowna

qua 10/1

11:55 am-5:35 pm

2 stops27h 40m

$704

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

dom 1/25

2:00 pm-11:55 pm

2 stops11h 55m

Kelowna

sáb 1/31

7:55 pm-12:01 pm

2 stops14h 06m

$815

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

qui 10/16

5:30 pm-11:39 pm

1 stop8h 09m

$92

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

sáb 9/27

6:15 am-1:21 pm

2 stops33h 06m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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, January is the cheapest month in which you can book a flight from Chicago to Kelowna (average of $399). Flying from Chicago to Kelowna in December is currently the most expensive (average of $662). 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.

What is the cheapest time of day to fly from CHI to YLW?

Find hourly flight availability from Chicago to Kelowna. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated setembro 15, 2025.

It’s optimal to fly from Chicago to Kelowna in the evening. By choosing this option you can save up to 74% on the cost of your flight, compared to a flight in the morning.

Reviews of airlines servicing Kelowna

Get insights into the airlines that provide service to Kelowna. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kelowna. Reviews last updated setembro 15, 2025.
Read reviews from past customers who have flown Air Canada from Chicago to Kelowna. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
10,000 reviews

Comfort

7.1

Entertainment

6.8

Food

6.3

Overall

7.1

Crew

7.8

Boarding

7.3

Reviews

1 / 20
8.0
Excellent

Graeme,Sep 2025

YWG - YVR

Why not start boarding from the higher seat numbers? Easier movement for everyone. Easier to put baggage in over head lockers. Unable to get a coffee due to air turbulence, but not offered the chance to have a coffee once it had ceased.
Air Canada
7.1
Good
10,000 reviews
Air Canada
7.1
Good
10,000 reviews

Comfort

7.1

Entertainment

6.8

Food

6.3

Overall

7.1

Crew

7.8

Boarding

7.3

Reviews

1 / 20
8.0
Excellent

Graeme,Sep 2025

YWG - YVR

Why not start boarding from the higher seat numbers? Easier movement for everyone. Easier to put baggage in over head lockers. Unable to get a coffee due to air turbulence, but not offered the chance to have a coffee once it had ceased.

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?

    For a flight from Chicago to Kelowna, you will be flying into Kelowna. Kelowna (YLW) is just 7.0 mi from the center of the city. Kelowna is the only Kelowna airport and it handles 0 inbound flights from Chicago per day. 3 airlines have flights to Kelowna from Chicago on a regular basis.

  • How long is the flight from Chicago to Kelowna?

    There are many flights that can get you from Chicago to Kelowna in 6h 48m. Fly via WestJet, Air Canada, or United Airlines to get the fastest option. There are 1594 mi between Chicago and Kelowna. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Chicago to Kelowna round-trip?

    Currently priced at $319, Air Canada will fly you from Chicago to Kelowna and back. In addition to Air Canada, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Alaska Airlines and United Airlines - these airlines can fly you to your destination from $408 and $432, respectively. Users have found that Air Canada is 34% cheaper than the other options available to this destination.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Kelowna (average of $399). Flying from Chicago to Kelowna in December is currently the most expensive (average of $662). 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

Traveling to a place near Kelowna?

Book flights to Kelowna if you plan to visit one of these locations
Salmon Arm

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Top 3 airlines flying from Chicago to Kelowna

Discover the top 3 airlines that operate flights from Chicago to Kelowna. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated setembro 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$319Average$909FlexibilityNo cancel feeOn-time67%
Alaska AirlinesCheapest$408Average$630FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$437Average$1,214FlexibilityNo cancel feeOn-time69%

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