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Kelowna

$112+ 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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YLW
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$269
(oojo)

One-way from

$112
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$545
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. 11% potential increase in price ($74 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This oojo deal was found by Cheapflights users on 7/29. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/175:30 pmORD - YLW
1 stop6h 19mWestJet
Mon 9/228:15 amYLW - ORD
1 stop6h 28mWestJet
Deal found 7/29$269
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
Sat 8/307:00 amORD - YLW
2 stops12h 44mMultiple Airlines
Tue 9/28:15 pmYLW - ORD
1 stop18h 28mMultiple Airlines
Deal found 7/28$341
This Alaska Airlines deal was found by Cheapflights users on 7/29. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/138:00 amORD - YLW
1 stop7h 57mAlaska Airlines
Sat 9/202:47 pmYLW - ORD
1 stop7h 16mAlaska Airlines
Deal found 7/29$343
This Air Canada deal was found by Cheapflights users on 7/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/273:40 pmORD - YLW
1 stop9h 08mAir Canada
Sun 8/317:15 amYLW - ORD
1 stop11h 01mAir Canada
Deal found 7/29$488
This Mytrip deal was found by Cheapflights users on 7/28. 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.
Fri 8/2910:45 amMDW - YLW
1 stop13h 40mMultiple Airlines
Mon 9/111:30 pmYLW - MDW
1 stop14h 54mMultiple Airlines
Deal found 7/28$596
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/319:20 amMDW - YLW
2 stops10h 02mDelta
Sat 11/89:05 amYLW - MDW
2 stops11h 09mDelta
Deal found 7/28$855
This Mytrip deal was found by Cheapflights users on 7/31. 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.
Fri 8/299:15 amMDW - YLW
2 stops15h 10mWestJet
Tue 9/28:15 pmYLW - MDW
3 stops19h 22mWestJet
Deal found 7/31$969

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 July 31, 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

Wed 9/17

5:30 pm-9:49 pm

1 stop6h 19m

Kelowna

Mon 9/22

8:15 am-4:43 pm

1 stop6h 28m

$269

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sat 8/30

7:00 am-5:44 pm

2 stops12h 44m

Kelowna

Tue 9/2

8:15 pm-4:43 pm

1 stop18h 28m

$341

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sat 9/13

8:00 am-1:57 pm

1 stop7h 57m

Kelowna

Sat 9/20

2:47 pm-12:03 am

1 stop7h 16m

$343

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Wed 8/27

3:40 pm-10:48 pm

1 stop9h 08m

Kelowna

Sun 8/31

7:15 am-8:16 pm

1 stop11h 01m

$488

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 8/29

10:45 am-10:25 pm

1 stop13h 40m

Kelowna

Mon 9/1

8:15 pm-4:24 pm

2 stops18h 09m

$596

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 10/31

9:20 am-5:22 pm

2 stops10h 02m

Kelowna

Sat 11/8

9:05 am-10:14 pm

2 stops11h 09m

$855

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 8/29

9:15 am-10:25 pm

2 stops15h 10m

Kelowna

Tue 9/2

8:15 pm-5:37 pm

3 stops19h 22m

$969

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sat 9/6

1:40 pm-11:30 pm

2 stops11h 50m

$112

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sat 8/30

7:00 am-5:44 pm

2 stops12h 44m

$182

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sat 8/30

6:20 am-1:57 pm

1 stop9h 37m

$202

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 17 results
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

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 July 31, 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 July 31, 2025.
Read reviews from past customers who have flown Alaska Airlines, Porter Airlines, and Delta 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Porter Airlines
8.0
Very good
318 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,900 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
WestJet
7.2
Good
2,978 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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.

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

    Currently priced at $269, WestJet will fly you from Chicago to Kelowna and back. In addition to WestJet, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Alaska Airlines and Air Canada - these airlines can fly you to your destination from $343 and $488, respectively. Users have found that WestJet is 51% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Chicago to Kelowna one-way?

    To fly one-way, consider booking your trip with WestJet, which is currently one of the cheapest options available, starting at $112. Alaska Airlines flights start at $202 while deals on Porter Airlines start at $347 one-way.

  • 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$342Average$1,214FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$370Average$909FlexibilityNo cancel feeOn-time67%
Alaska AirlinesCheapest$414Average$630FlexibilityNo cancel feeOn-time75%

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