HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kelowna

$99+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YLW
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Kelowna with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 February 3, 2026.

This Trip.com deal was found by Cheapflights users on 2/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/102:20 pm
ORD
-
YLW
1 stop6h 48m
WestJet
Fri 4/175:20 am
YLW
-
ORD
1 stop6h 15m
WestJet
Deal found 2/1$228
This Air Canada deal was found by Cheapflights users on 1/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/33:35 pm
ORD
-
YLW
1 stop9h 38m
Air Canada
Wed 3/45:20 am
YLW
-
ORD
1 stop7h 21m
Air Canada
Deal found 1/31$239
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Mon 3/22:20 pm
ORD
-
YLW
1 stop6h 48m
WestJet
Fri 3/65:20 am
YLW
-
ORD
1 stop6h 15m
WestJet
Deal found 2/1$315
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 4/102:20 pm
ORD
-
YLW
1 stop6h 48m
Multiple Airlines
Fri 4/177:35 pm
YLW
-
ORD
2 stops13h 09m
Multiple Airlines
Deal found 2/1$334
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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.
Tue 3/33:54 pm
ORD
-
YLW
1 stop7h 18m
Alaska Airlines
Wed 3/41:35 pm
YLW
-
ORD
1 stop8h 21m
Alaska Airlines
Deal found 2/2$337
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/46:02 pm
ORD
-
YLW
2 stops26h 03m
Multiple Airlines
Wed 3/112:55 pm
YLW
-
ORD
1 stop11h 54m
Multiple Airlines
Deal found 2/2$379
This Orbitz deal was found by Cheapflights users on 2/3. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/13:54 pm
ORD
-
YLW
1 stop7h 18m
Multiple Airlines
Fri 3/205:20 am
YLW
-
ORD
1 stop6h 15m
Multiple Airlines
Deal found 2/3$403
This Mytrip deal was found by Cheapflights users on 2/1. 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.
Mon 3/211:00 am
MDW
-
YLW
2 stops14h 12m
Multiple Airlines
Fri 3/611:40 pm
YLW
-
MDW
1 stop10h 10m
Multiple Airlines
Deal found 2/1$563
This Justfly.com deal was found by Cheapflights users on 2/2. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/119:53 am
MDW
-
YLW
2 stops25h 36m
WestJet
Sun 2/226:35 pm
YLW
-
MDW
2 stops13h 19m
WestJet
Deal found 2/2$947
This FlightHub deal was found by Cheapflights users on 2/3. 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.
Thu 2/267:20 pm
MDW
-
YLW
2 stops24h 41m
WestJet
Sun 3/14:00 pm
YLW
-
MDW
2 stops24h 40m
WestJet
Deal found 2/3$980
This FlightHub deal was found by Cheapflights users on 2/1. 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 2/1110:46 am
MDW
-
YLW
2 stops13h 02m
WestJet
Sun 2/157:35 pm
YLW
-
MDW
2 stops12h 19m
WestJet
Deal found 2/1$984
This WestJet deal was found by Cheapflights users on 2/2. 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.
Mon 3/21:49 pm
MDW
-
YLW
2 stops44h 11m
WestJet
Wed 3/410:10 am
YLW
-
MDW
2 stops30h 30m
WestJet
Deal found 2/2$1,047

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 February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$228
(Trip.com)

One-way from

$99
(Air Canada)

Popular in

October

Cheapest in

July

Average price

$530
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. 26% potential increase in price ($198 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($58 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 3, 2026.
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

Tue 3/3

3:35 pm-11:13 pm

1 stop9h 38m

Kelowna

Wed 3/4

5:20 am-2:41 pm

1 stop7h 21m

$239

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Fri 4/10

2:20 pm-7:08 pm

1 stop6h 48m

Kelowna

Fri 4/17

7:35 pm-10:44 am

2 stops13h 09m

$334

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 3/3

3:54 pm-9:12 pm

1 stop7h 18m

Kelowna

Wed 3/4

1:35 pm-11:56 pm

1 stop8h 21m

$337

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Mon 3/2

2:20 pm-11:12 pm

2 stops10h 52m

Kelowna

Fri 3/6

5:20 am-1:35 pm

1 stop6h 15m

$359

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sun 3/1

3:54 pm-9:12 pm

1 stop7h 18m

Kelowna

Fri 3/20

5:20 am-1:35 pm

1 stop6h 15m

$403

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Wed 3/4

3:35 pm-11:13 pm

1 stop9h 38m

Kelowna

Wed 3/11

8:30 pm-2:41 pm

1 stop16h 11m

$411

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sat 3/14

7:39 pm-2:05 pm

1 stop20h 26m

Kelowna

Thu 3/19

5:45 pm-1:35 pm

2 stops17h 50m

$419

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 3/2

11:00 am-11:12 pm

2 stops14h 12m

Kelowna

Fri 3/6

11:40 pm-11:50 am

1 stop10h 10m

$563

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 2/26

7:20 pm-6:01 pm

2 stops24h 41m

Kelowna

Sun 3/1

4:00 pm-6:40 pm

2 stops24h 40m

$980

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 3/2

9:50 am-8:00 am

2 stops48h 10m

Kelowna

Wed 3/4

10:10 am-6:40 pm

2 stops30h 30m

$1,047

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/31

Showing 1-10 of 28 results
1
2
3
  • Most accurate provider: When it comes to deals on Chicago-Kelowna flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Kelowna flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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

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

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 7h 18m. Fly via Air Canada, Alaska Airlines, or WestJet 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 $379, respectively. Users have found that United Airlines is 69% 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$166Average$947FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$319Average$909FlexibilityNo cancel feeOn-time67%
Alaska AirlinesCheapest$379Average$630FlexibilityNo cancel feeOn-time75%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights