$200+ Cheap flights from Chicago (CHI) to Kelowna (YLW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YLW
Oct 29 — Nov 51
Round-trip
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
Best
Last-minute
One-way
Cheapest flights from Chicago to KelownaExplore 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 September 29, 2026.
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 September 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 10/165:30 pm -
1 stop8h 20m
Mon 10/198:15 pm -
2 stops31h 25m
Deal found 9/27![Multiple Airlines logo]()
$411
This Air Canada deal was found by Cheapflights users on 9/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/123:30 pm -
1 stop18h 38m
Thu 11/195:50 am -
1 stop6h 47m
Deal found 9/28![Air Canada logo]()
$424
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 10/155:30 pm -
1 stop6h 35m
Mon 10/198:15 pm -
2 stops31h 25m
Deal found 9/27![Multiple Airlines logo]()
$425
This Air Canada deal was found by Cheapflights users on 9/25. 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.
Mon 11/93:30 pm -
1 stop18h 38m
Mon 11/169:20 pm -
1 stop15h 17m
Deal found 9/25![Air Canada logo]()
$443
This Orbitz deal was found by Cheapflights users on 9/27. 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.
Wed 12/93:19 pm -
1 stop9h 18m
Sun 12/137:00 am -
1 stop8h 49m
Deal found 9/27![Alaska Airlines logo]()
$445
This Air Canada deal was found by Cheapflights users on 9/27. 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 10/153:40 pm -
1 stop9h 47m
Mon 10/1910:50 pm -
1 stop8h 10m
Deal found 9/27![Air Canada logo]()
$452
This Air Canada deal was found by Cheapflights users on 9/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:40 pm -
1 stop18h 35m
Tue 11/39:20 pm -
2 stops10h 03m
Deal found 9/28![Air Canada logo]()
$466
This Kiwi.com deal was found by Cheapflights users on 9/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:30 pm -
1 stop6h 35m
Tue 10/208:45 pm -
2 stops31h 49m
Deal found 9/29![Multiple Airlines logo]()
$510
This Travelocity deal was found by Cheapflights users on 9/29. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:46 pm -
1 stop21h 11m
Tue 10/201:47 pm -
1 stop13h 53m
Deal found 9/29![Alaska Airlines logo]()
$516
Best flights from Chicago to KelownaDiscover carefully curated flight deals from Chicago to Kelowna that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 29, 2026.
Discover carefully curated flight deals from Chicago to Kelowna that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 29, 2026.
This Mytrip deal was found by Cheapflights users on 9/25. 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 2/264:30 pm -
1 stop8h 55m
Sat 3/612:20 am -
1 stop6h 48m
Deal found 9/25![Air Canada logo]()
$391
This Alaska Airlines deal was found by Cheapflights users on 9/29. 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.
Thu 1/218:00 am -
1 stop16h 34m
Wed 1/272:28 pm -
2 stops20h 45m
Deal found 9/29![Alaska Airlines logo]()
$464
This Delta deal was found by Cheapflights users on 9/28. 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.
Thu 11/127:30 am -
2 stops11h 00m
Thu 11/199:15 am -
2 stops10h 32m
Deal found 9/28![Delta logo]()
$536
This Air Canada deal was found by Cheapflights users on 9/25. 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.
Mon 11/93:30 pm -
1 stop18h 38m
Mon 11/169:20 pm -
1 stop15h 17m
Deal found 9/25![Air Canada logo]()
$443
This Air Canada deal was found by Cheapflights users on 9/26. 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 3/33:40 pm -
1 stop8h 47m
Sat 3/612:20 am -
1 stop6h 48m
Deal found 9/26![Air Canada logo]()
$465
This Alaska Airlines deal was found by Cheapflights users on 9/27. 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 1/58:00 am -
1 stop16h 34m
Fri 1/152:28 pm -
2 stops20h 45m
Deal found 9/27![Alaska Airlines logo]()
$515
This Air Canada deal was found by Cheapflights users on 9/24. 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.
Sat 10/318:40 pm -
1 stop18h 35m
Tue 11/39:20 pm -
2 stops10h 03m
Deal found 9/24![Air Canada logo]()
$466
This Orbitz deal was found by Cheapflights users on 9/26. 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.
Wed 3/32:03 pm -
2 stops10h 09m
Mon 3/87:00 am -
2 stops28h 09m
Deal found 9/26![Alaska Airlines logo]()
$520
Last-minute flights from Chicago to KelownaDiscover last-minute flight deals from Chicago to Kelowna. Data last updated September 29, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kelowna. Data last updated September 29, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 10/155:30 pm -
1 stop6h 35m
Mon 10/198:15 pm -
2 stops31h 25m
Deal found 9/27![Multiple Airlines logo]()
$425
This Air Canada deal was found by Cheapflights users on 9/27. 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 10/153:40 pm -
1 stop9h 47m
Mon 10/1910:50 pm -
1 stop8h 10m
Deal found 9/27![Air Canada logo]()
$452
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 10/165:30 pm -
1 stop8h 20m
Mon 10/198:15 pm -
2 stops31h 25m
Deal found 9/27![Multiple Airlines logo]()
$411
This Kiwi.com deal was found by Cheapflights users on 9/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:30 pm -
1 stop6h 35m
Tue 10/208:45 pm -
2 stops31h 49m
Deal found 9/29![Multiple Airlines logo]()
$510
This Travelocity deal was found by Cheapflights users on 9/29. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:46 pm -
1 stop21h 11m
Tue 10/201:47 pm -
1 stop13h 53m
Deal found 9/29![Alaska Airlines logo]()
$516
This Air Canada deal was found by Cheapflights users on 9/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:40 pm -
1 stop18h 35m
Tue 11/39:20 pm -
2 stops10h 03m
Deal found 9/28![Air Canada logo]()
$466
One-way flights from Chicago to KelownaSearch for one-way flight options from Chicago to Kelowna. Find affordable one-way fares based on user searches. Data last updated September 29, 2026.
Search for one-way flight options from Chicago to Kelowna. Find affordable one-way fares based on user searches. Data last updated September 29, 2026.
This Air Canada deal was found by Cheapflights users on 9/25. 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.
Mon 11/93:30 pm -
1 stop18h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Air Canada logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 11/97:50 pm -
2 stops20h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$234
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 September 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $391 (Mytrip) |
One-way from | $200 (Air Canada) |
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 7,457,451 searches. Data last updated September 29, 2026.
Use the filters below to find and compare flights from Chicago to Kelowna that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoKelowna
ORD Chicago O'Hare Intl - YLW Kelowna
ORDYLW
Chicago O'Hare Intl
Mon 11/9
3:30 pm-9:08 am
1 stop18h 38m
Kelowna
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$200
ChicagoKelowna
ORD Chicago O'Hare Intl - YLW Kelowna
ORDYLW
Chicago O'Hare Intl
Mon 11/9
6:30 am-10:55 am
3 stops29h 25m
Kelowna
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$258
ChicagoKelowna
ORD Chicago O'Hare Intl - YLW Kelowna
ORDYLW
Chicago O'Hare Intl
Fri 2/26
4:30 pm-12:25 am
1 stop8h 55m
Kelowna
Sat 3/6
12:20 am-8:08 am
1 stop6h 48m
$391
ChicagoKelowna
ORD Chicago O'Hare Intl - YLW Kelowna
ORDYLW
Chicago O'Hare Intl
Mon 11/9
3:30 pm-9:08 am
1 stop18h 38m
Kelowna
Mon 11/16
9:20 pm-1:37 pm
1 stop15h 17m
$443
ChicagoKelowna
ORD Chicago O'Hare Intl - YLW Kelowna
ORDYLW
Chicago O'Hare Intl
Thu 1/21
8:00 am-11:34 pm
1 stop16h 34m
Kelowna
Wed 1/27
2:28 pm-12:13 pm
2 stops20h 45m
$464
Quickest round-trip
ChicagoKelowna
ORD Chicago O'Hare Intl - YLW Kelowna
ORDYLW
Chicago O'Hare Intl
Wed 3/3
3:40 pm-11:27 pm
1 stop8h 47m
Kelowna
Sat 3/6
12:20 am-8:08 am
1 stop6h 48m
$465
ChicagoKelowna
ORD Chicago O'Hare Intl - YLW Kelowna
ORDYLW
Chicago O'Hare Intl
Sat 10/31
8:40 pm-1:15 pm
1 stop18h 35m
Kelowna
Tue 11/3
9:20 pm-8:23 am
2 stops10h 03m
$466
ChicagoKelowna
ORD Chicago O'Hare Intl - YLW Kelowna
ORDYLW
Chicago O'Hare Intl
Tue 1/5
8:00 am-11:34 pm
1 stop16h 34m
Kelowna
Fri 1/15
2:28 pm-12:13 pm
2 stops20h 45m
$515
ChicagoKelowna
ORD Chicago O'Hare Intl - YLW Kelowna
ORDYLW
Chicago O'Hare Intl
Wed 3/3
2:03 pm-11:12 pm
2 stops10h 09m
Kelowna
Mon 3/8
7:00 am-12:09 pm
2 stops28h 09m
$520
ChicagoKelowna
ORD Chicago O'Hare Intl - YLW Kelowna
ORDYLW
Chicago O'Hare Intl
Thu 11/12
7:30 am-5:30 pm
2 stops11h 00m
Kelowna
Thu 11/19
9:15 am-8:47 pm
2 stops10h 32m
$536
Sorted by cheapest first
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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- 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.
CHI-YLW
ORD-YLW
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
CHI-YLW
ORD-YLW
No data available for this route at this time. Please check back soon.
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 September 29, 2026.
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.
Comfort
7.1
Entertainment
6.8
Crew
7.8
Food
6.3
Boarding
7.3
Overall
7.1
Reviews
1 / 20
6.0
GoodAnonymous,Aug 2026
PDX - YVR
Comfort
7.1
Entertainment
6.8
Crew
7.8
Food
6.3
Boarding
7.3
Overall
7.1
Reviews
1 / 20
6.0
GoodAnonymous,Aug 2026
PDX - YVR
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.
Traveling to a place near Kelowna?
Book flights to Kelowna if you plan to visit one of these locationsWest Kelowna
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.
Alternative routes
Complete your trip
Flights by cabin class
Kelowna flight routes
Other flight options
Other flights from Chicago
Popular flights
Alternative routes for Chicago to Kelowna
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Kelowna by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Kelowna by cabin class
Find flights from Chicago to Kelowna, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Kelowna
Explore flights to Kelowna departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 29, 2026.
Chicago and Kelowna flights
Browse other Chicago and Kelowna flight options. Last updated on September 29, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on September 29, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Chicago to Kelowna
Discover the top 2 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 7,457,451 searches. Data last updated September 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$140 | Average$468 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$178 | Average$341 | FlexibilityNo cancel fee | On-time60% |