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Kelowna

$87+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YLW
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Thu 12/257:25 amORD - YLW
2 stops15h 29mWestJet
Fri 1/95:20 amYLW - ORD
1 stop6h 15mWestJet
Deal found 12/17$556
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/274:30 pmORD - YLW
2 stops52h 46mMultiple Airlines
Fri 1/95:20 amYLW - ORD
1 stop6h 15mMultiple Airlines
Deal found 12/17$565
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Fri 12/264:30 pmORD - YLW
2 stops30h 11mMultiple Airlines
Fri 1/95:20 amYLW - ORD
1 stop6h 15mMultiple Airlines
Deal found 12/17$609
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Wed 12/247:00 amORD - YLW
2 stops34h 00mMultiple Airlines
Fri 1/95:20 amYLW - ORD
1 stop6h 15mMultiple Airlines
Deal found 12/17$636
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Wed 12/247:00 amORD - YLW
2 stops34h 00mMultiple Airlines
Mon 1/125:20 amYLW - ORD
1 stop6h 15mMultiple Airlines
Deal found 12/17$678
This Air Canada deal was found by Cheapflights users on 12/17. 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.
Thu 12/257:10 amORD - YLW
2 stops12h 28mAir Canada
Fri 1/910:25 amYLW - ORD
2 stops16h 50mAir Canada
Deal found 12/17$679
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Thu 12/253:27 pmORD - YLW
1 stop9h 48mMultiple Airlines
Fri 1/95:20 amYLW - ORD
1 stop6h 15mMultiple Airlines
Deal found 12/17$691
This Delta deal was found by Cheapflights users on 12/17. 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 12/269:29 amMDW - YLW
2 stops15h 15mDelta
Fri 1/99:00 amYLW - MDW
2 stops29h 16mDelta
Deal found 12/17$929
This FlightHub deal was found by Cheapflights users on 12/17. 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.
Wed 12/249:50 amMDW - YLW
2 stops37h 04mWestJet
Tue 1/64:00 pmYLW - MDW
2 stops24h 32mWestJet
Deal found 12/17$944
This Delta deal was found by Cheapflights users on 12/17. 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.
Thu 12/256:08 pmMDW - YLW
2 stops30h 36mDelta
Fri 1/99:00 amYLW - MDW
2 stops29h 16mDelta
Deal found 12/17$979
This WestJet deal was found by Cheapflights users on 12/17. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/249:50 amMDW - YLW
2 stops50h 11mWestJet
Mon 1/127:00 pmYLW - MDW
2 stops13h 27mWestJet
Deal found 12/17$1,003
This WestJet deal was found by Cheapflights users on 12/17. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/249:50 amMDW - YLW
2 stops48h 15mWestJet
Thu 1/811:40 pmYLW - MDW
2 stops31h 12mWestJet
Deal found 12/17$1,009

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$201
(Kiwi.com)

One-way from

$87
(Kiwi.com)

Popular in

October

Cheapest in

March

Average price

$1,054
Provider with most accurate pricing for Chicago (CHI)-Kelowna flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Kelowna flights.
Search Deals
From Chicago (CHI) to Kelowna
Search Deals
One-way flight from Chicago (CHI) to Kelowna
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($172 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($56 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 2,558,603 searches. Data last updated December 18, 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

Sat 1/31

8:00 am-6:59 pm

2 stops12h 59m

Kelowna

Sat 2/7

9:05 am-11:50 pm

1 stop12h 45m

$253

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Thu 2/26

9:00 am-7:08 pm

2 stops12h 08m

Kelowna

Sun 3/1

7:55 pm-1:35 pm

1 stop15h 40m

$255

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Thu 1/8

6:06 pm-1:15 pm

1 stop21h 09m

Kelowna

Tue 1/13

7:55 pm-12:08 pm

2 stops14h 13m

$257

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Wed 1/21

2:18 pm-7:10 pm

2 stops30h 52m

Kelowna

Sun 1/25

7:55 pm-1:35 pm

1 stop15h 40m

$258

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Fri 1/30

2:20 pm-7:10 pm

1 stop6h 50m

Kelowna

Mon 2/2

5:20 am-1:35 pm

1 stop6h 15m

$260

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Wed 3/11

3:54 pm-9:12 pm

1 stop7h 18m

Kelowna

Mon 3/16

5:20 am-1:35 pm

1 stop6h 15m

$267

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 2/22

9:04 pm-8:50 pm

2 stops25h 46m

Kelowna

Thu 2/26

7:00 am-11:51 pm

1 stop14h 51m

$274

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 1/13

3:35 pm-11:13 pm

1 stop9h 38m

Kelowna

Sun 1/18

5:20 am-2:41 pm

1 stop7h 21m

$285

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Wed 3/11

3:59 pm-11:53 pm

2 stops9h 54m

Kelowna

Mon 3/16

5:20 am-1:35 pm

1 stop6h 15m

$287

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Thu 2/26

1:05 pm-11:13 pm

1 stop12h 08m

Kelowna

Sun 3/1

11:25 pm-9:50 am

1 stop8h 25m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 27 results
1
2
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Compare providers for flights from Chicago to Kelowna

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Kelowna in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Kelowna flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Kelowna flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Kelowna flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Kelowna flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Kelowna flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 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 December 18, 2025.

It’s optimal to fly from Chicago to Kelowna in the evening. By choosing this option you can save up to 71% on the cost of your flight, compared to a flight at noon.

How much does it cost to fly round-trip from Chicago to Kelowna?

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 December 18, 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
10,534 reviews

Entertainment

6.8

Crew

7.8

Overall

7.1

Boarding

7.3

Food

6.3

Comfort

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SIN - YVR

In the last portion of flight Singapore -Miami after a 14 hr flight, then the flight from Vancouver -Miami they were selling the food very ugly portion for a flight of 6 hours regardless if you treat that flight as domestic , I was impressed with the service but now l will not book a flight with air Canada
Air Canada
7.1
Good
10,534 reviews
Air Canada
7.1
Good
10,534 reviews

Entertainment

6.8

Crew

7.8

Overall

7.1

Boarding

7.3

Food

6.3

Comfort

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SIN - YVR

In the last portion of flight Singapore -Miami after a 14 hr flight, then the flight from Vancouver -Miami they were selling the food very ugly portion for a flight of 6 hours regardless if you treat that flight as domestic , I was impressed with the service but now l will not book a flight with air Canada

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 50m. Fly via WestJet or Delta 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 $166, United Airlines will fly you from Chicago to Kelowna and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Air Canada and Alaska Airlines - these airlines can fly you to your destination from $319 and $342, respectively. Users have found that United Airlines is 71% 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.

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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$319Average$913FlexibilityNo cancel feeOn-time67%
Alaska AirlinesCheapest$342Average$650FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$370Average$947FlexibilityNo cancel feeOn-time69%

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