$193+ 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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YLW
Jul 7 — Jul 141
Round-trip
1 adult, Economy
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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
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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
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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 June 7, 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 June 7, 2026.
This Booking.com deal was found by Cheapflights users on 6/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/205:30 pm
ORD
- YLW
1 stop8h 20m
WestJet
Mon 7/277:50 am
YLW
- ORD
1 stop6h 50m
WestJet
Deal found 6/4![WestJet logo]()
$481
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Tue 7/219:13 pm
ORD
- YLW
2 stops22h 47m
Multiple Airlines
Fri 7/241:46 pm
YLW
- ORD
1 stop8h 13m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$529
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/205:30 pm
ORD
- YLW
1 stop16h 50m
Multiple Airlines
Mon 7/278:15 pm
YLW
- ORD
2 stops22h 37m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$530
This Alaska Airlines deal was found by Cheapflights users on 6/6. 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.
Mon 10/56:00 am
ORD
- YLW
1 stop8h 57m
Alaska Airlines
Wed 10/71:47 pm
YLW
- ORD
1 stop8h 12m
Alaska Airlines
Deal found 6/6![Alaska Airlines logo]()
$532
This Expedia deal was found by Cheapflights users on 6/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/18:20 pm
ORD
- YLW
1 stop18h 36m
Alaska Airlines
Wed 8/51:46 pm
YLW
- ORD
1 stop8h 13m
Alaska Airlines
Deal found 6/7![Alaska Airlines logo]()
$541
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
Sun 8/26:00 am
ORD
- YLW
1 stop8h 56m
Multiple Airlines
Thu 8/67:50 am
YLW
- ORD
1 stop6h 50m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$542
This Air Canada deal was found by Cheapflights users on 6/4. 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 7/23:40 pm
ORD
- YLW
1 stop9h 49m
Air Canada
Thu 7/911:00 pm
YLW
- ORD
1 stop8h 00m
Air Canada
Deal found 6/4![Air Canada logo]()
$551
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 8/11:50 pm
ORD
- YLW
2 stops25h 30m
Multiple Airlines
Wed 8/58:15 pm
YLW
- ORD
1 stop18h 25m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$567
This FlightHub deal was found by Cheapflights users on 6/6. 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.
Tue 8/115:30 pm
ORD
- YLW
1 stop6h 35m
WestJet
Sun 8/1612:05 pm
YLW
- ORD
1 stop26h 35m
WestJet
Deal found 6/6![WestJet logo]()
$574
This Kiwi.com deal was found by Cheapflights users on 6/2. 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.
Fri 7/36:19 pm
ORD
- YLW
2 stops27h 46m
Multiple Airlines
Fri 7/101:46 pm
YLW
- ORD
1 stop8h 13m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$577
This Alaska Airlines deal was found by Cheapflights users on 6/7. 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 8/113:43 pm
ORD
- YLW
1 stop23h 13m
Alaska Airlines
Sun 8/161:46 pm
YLW
- ORD
1 stop8h 13m
Alaska Airlines
Deal found 6/7![Alaska Airlines logo]()
$593
This Mytrip deal was found by Cheapflights users on 6/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/3010:25 am
MDW
- YLW
2 stops13h 40m
Multiple Airlines
Tue 7/712:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$639
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 June 7, 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 June 7, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/6. 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.
Mon 10/56:00 am
ORD
- YLW
1 stop8h 57m
Alaska Airlines
Wed 10/71:47 pm
YLW
- ORD
1 stop8h 12m
Alaska Airlines
Deal found 6/6![Alaska Airlines logo]()
$532
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
Sun 8/26:00 am
ORD
- YLW
1 stop8h 56m
Multiple Airlines
Thu 8/67:50 am
YLW
- ORD
1 stop6h 50m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$542
This FlightHub deal was found by Cheapflights users on 6/6. 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.
Tue 8/115:30 pm
ORD
- YLW
1 stop6h 35m
WestJet
Sun 8/1612:05 pm
YLW
- ORD
1 stop26h 35m
WestJet
Deal found 6/6![WestJet logo]()
$574
This Air Canada deal was found by Cheapflights users on 6/2. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/183:40 pm
ORD
- YLW
1 stop9h 49m
Air Canada
Wed 8/195:25 am
YLW
- ORD
1 stop7h 11m
Air Canada
Deal found 6/2![Air Canada logo]()
$599
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/2010:25 am
MDW
- YLW
1 stop13h 27m
Porter Airlines
Mon 7/2710:50 pm
YLW
- MDW
1 stop13h 45m
Porter Airlines
Deal found 6/4![Porter Airlines logo]()
$712
This Kiwi.com deal was found by Cheapflights users on 6/2. 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.
Fri 7/36:19 pm
ORD
- YLW
2 stops27h 46m
Multiple Airlines
Fri 7/101:46 pm
YLW
- ORD
1 stop8h 13m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$577
This Alaska Airlines deal was found by Cheapflights users on 6/7. 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 8/113:43 pm
ORD
- YLW
1 stop23h 13m
Alaska Airlines
Sun 8/161:46 pm
YLW
- ORD
1 stop8h 13m
Alaska Airlines
Deal found 6/7![Alaska Airlines logo]()
$593
This Mytrip deal was found by Cheapflights users on 6/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/3010:25 am
MDW
- YLW
2 stops13h 40m
Multiple Airlines
Tue 7/712:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$639
This Mytrip deal was found by Cheapflights users on 6/4. 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 7/2010:25 am
MDW
- YLW
1 stop13h 27m
Multiple Airlines
Mon 7/273:15 pm
YLW
- MDW
2 stops16h 25m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$699
This Kiwi.com deal was found by Cheapflights users on 6/2. 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.
Mon 6/293:20 pm
MDW
- YLW
1 stop21h 27m
Porter Airlines
Sun 7/510:50 pm
YLW
- MDW
1 stop13h 45m
Porter Airlines
Deal found 6/2![Porter Airlines logo]()
$923
This Mytrip deal was found by Cheapflights users on 6/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/249:54 am
MDW
- YLW
3 stops28h 01m
Multiple Airlines
Tue 6/3012:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$753
This Mytrip deal was found by Cheapflights users on 6/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/91:49 pm
MDW
- YLW
2 stops34h 03m
Multiple Airlines
Tue 7/1412:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$762
This Mytrip deal was found by Cheapflights users on 6/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/2910:25 am
MDW
- YLW
2 stops15h 25m
Multiple Airlines
Sun 7/57:50 pm
YLW
- MDW
2 stops16h 45m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$770
This Mytrip deal was found by Cheapflights users on 6/4. 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.
Tue 7/219:54 am
MDW
- YLW
2 stops11h 06m
Multiple Airlines
Fri 7/2412:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$915
This Mytrip deal was found by Cheapflights users on 6/4. 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.
Sat 7/1110:25 am
MDW
- YLW
3 stops23h 55m
Multiple Airlines
Fri 7/179:05 pm
YLW
- MDW
3 stops34h 08m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$940
Last-minute flights from Chicago to KelownaDiscover last-minute flight deals from Chicago to Kelowna. Data last updated June 7, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kelowna. Data last updated June 7, 2026 and is based on user searches.
This United deal was found by Cheapflights users on 6/3. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/243:40 pm
ORD
- YLW
1 stop9h 49m
Multiple Airlines
Tue 6/3011:00 pm
YLW
- ORD
1 stop8h 00m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$670
This Kiwi.com deal was found by Cheapflights users on 6/2. 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.
Mon 6/2910:25 am
MDW
- YLW
2 stops25h 20m
Multiple Airlines
Sun 7/510:50 pm
YLW
- MDW
1 stop13h 45m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$693
This Mytrip deal was found by Cheapflights users on 6/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/3010:25 am
MDW
- YLW
2 stops13h 40m
Multiple Airlines
Tue 7/712:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$639
This Air Canada deal was found by Cheapflights users on 6/4. 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 7/23:40 pm
ORD
- YLW
1 stop9h 49m
Air Canada
Thu 7/911:00 pm
YLW
- ORD
1 stop8h 00m
Air Canada
Deal found 6/4![Air Canada logo]()
$551
This FlightHub deal was found by Cheapflights users on 6/4. 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 7/25:30 pm
ORD
- YLW
1 stop16h 50m
Multiple Airlines
Thu 7/91:46 pm
YLW
- ORD
1 stop8h 13m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$683
This Kiwi.com deal was found by Cheapflights users on 6/2. 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.
Fri 7/36:19 pm
ORD
- YLW
2 stops27h 46m
Multiple Airlines
Fri 7/101:46 pm
YLW
- ORD
1 stop8h 13m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$577
This Kiwi.com deal was found by Cheapflights users on 6/2. 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.
Thu 7/99:57 pm
ORD
- YLW
2 stops21h 03m
Multiple Airlines
Tue 7/141:46 pm
YLW
- ORD
1 stop8h 13m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$616
This Mytrip deal was found by Cheapflights users on 6/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/910:25 am
MDW
- YLW
3 stops22h 35m
Multiple Airlines
Tue 7/1412:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$663
This oojo deal was found by Cheapflights users on 6/7. 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.
Thu 7/165:30 pm
ORD
- YLW
1 stop16h 50m
WestJet
Thu 7/235:05 am
YLW
- ORD
1 stop9h 35m
WestJet
Deal found 6/7![WestJet logo]()
$629
This Booking.com deal was found by Cheapflights users on 6/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/205:30 pm
ORD
- YLW
1 stop8h 20m
WestJet
Mon 7/277:50 am
YLW
- ORD
1 stop6h 50m
WestJet
Deal found 6/4![WestJet logo]()
$481
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/205:30 pm
ORD
- YLW
1 stop16h 50m
Multiple Airlines
Mon 7/278:15 pm
YLW
- ORD
2 stops22h 37m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$530
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Tue 7/219:13 pm
ORD
- YLW
2 stops22h 47m
Multiple Airlines
Fri 7/241:46 pm
YLW
- ORD
1 stop8h 13m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$529
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 June 7, 2026.
Search for one-way flight options from Chicago to Kelowna. Find affordable one-way fares based on user searches. Data last updated June 7, 2026.
This Air Canada deal was found by Cheapflights users on 6/2. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/53:40 pm
ORD
- YLW
1 stop9h 38m
Air Canada
Deal found 6/2![Air Canada logo]()
$193
This Alaska Airlines deal was found by Cheapflights users on 6/2. 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.
Thu 11/52:07 pm
ORD
- YLW
2 stops26h 39m
Alaska Airlines
Deal found 6/2![Alaska Airlines logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/16:24 pm
ORD
- YLW
3 stops29h 41m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 6/2. 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.
Thu 11/52:46 pm
ORD
- YLW
3 stops25h 36m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$306
This Air Canada deal was found by Cheapflights users on 6/4. 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 7/13:40 pm
ORD
- YLW
1 stop9h 49m
Air Canada
Deal found 6/4![Air Canada logo]()
$365
This Air Canada deal was found by Cheapflights users on 6/2. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/188:40 am
ORD
- YLW
1 stop12h 13m
Air Canada
Deal found 6/2![Air Canada logo]()
$373
This Air Canada deal was found by Cheapflights users on 6/2. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/32:15 pm
ORD
- YLW
1 stop9h 46m
Air Canada
Deal found 6/2![Air Canada logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 6/2. 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 6/171:40 am
ORD
- YLW
3 stops32h 40m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$393
This Alaska Airlines deal was found by Cheapflights users on 6/2. 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.
Fri 7/32:12 pm
ORD
- YLW
2 stops24h 44m
Alaska Airlines
Deal found 6/2![Alaska Airlines logo]()
$427
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/110:25 am
MDW
- YLW
3 stops22h 35m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$435
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/110:25 am
MDW
- YLW
2 stops51h 30m
Porter Airlines
Deal found 6/4![Porter Airlines logo]()
$455
This Porter Airlines deal was found by Cheapflights users on 6/2. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/33:20 pm
MDW
- YLW
2 stops22h 35m
Porter Airlines
Deal found 6/2![Porter Airlines logo]()
$534
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 June 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $481 (Booking.com) |
One-way from | $193 (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 2,558,603 searches. Data last updated June 7, 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 - YLW
ORDYLW
Chicago O'Hare Intl
Mon 10/5
6:00 am-12:57 pm
1 stop8h 57m
Kelowna
Wed 10/7
1:47 pm-11:59 pm
1 stop8h 12m
$532
Quickest round-trip
ChicagoKelowna
ORD - YLW
ORDYLW
Chicago O'Hare Intl
Sun 8/2
6:00 am-12:56 pm
1 stop8h 56m
Kelowna
Thu 8/6
7:50 am-4:40 pm
1 stop6h 50m
$542
ChicagoKelowna
ORD - YLW
ORDYLW
Chicago O'Hare Intl
Tue 8/11
5:30 pm-10:05 pm
1 stop6h 35m
Kelowna
Sun 8/16
12:05 pm-4:40 pm
1 stop26h 35m
$574
ChicagoKelowna
ORD - YLW
ORDYLW
Chicago O'Hare Intl
Fri 7/3
6:19 pm-8:05 pm
2 stops27h 46m
Kelowna
Fri 7/10
1:46 pm-11:59 pm
1 stop8h 13m
$577
ChicagoKelowna
ORD - YLW
ORDYLW
Chicago O'Hare Intl
Tue 8/11
3:43 pm-12:56 pm
1 stop23h 13m
Kelowna
Sun 8/16
1:46 pm-11:59 pm
1 stop8h 13m
$593
ChicagoKelowna
ORD - YLW
ORDYLW
Chicago O'Hare Intl
Tue 8/18
3:40 pm-11:29 pm
1 stop9h 49m
Kelowna
Wed 8/19
5:25 am-2:36 pm
1 stop7h 11m
$599
ChicagoKelowna
MDW - YLW
MDWYLW
Chicago Midway
Tue 6/30
10:25 am-10:05 pm
2 stops13h 40m
Kelowna
Tue 7/7
12:50 pm-9:40 am
2 stops18h 50m
$639
ChicagoKelowna
MDW - YLW
MDWYLW
Chicago Midway
Mon 7/20
10:25 am-9:52 pm
1 stop13h 27m
Kelowna
Mon 7/27
3:15 pm-9:40 am
2 stops16h 25m
$699
ChicagoKelowna
MDW - YLW
MDWYLW
Chicago Midway
Mon 7/20
10:25 am-9:52 pm
1 stop13h 27m
Kelowna
Mon 7/27
10:50 pm-2:35 pm
1 stop13h 45m
$712
ChicagoKelowna
MDW - YLW
MDWYLW
Chicago Midway
Wed 6/24
9:54 am-11:55 am
3 stops28h 01m
Kelowna
Tue 6/30
12:50 pm-9:40 am
2 stops18h 50m
$753
Showing 1-10 of 27 resultsSorted 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 June.
| 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
MDW-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
MDW-YLW
No data available for this route at this time. Please check back soon.
Related info for your journey
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Traveling to a place near Kelowna?
Book flights to Kelowna if you plan to visit one of these locationsWest Kelowna
Salmon Arm
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Other flights to Kelowna
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Chicago and Kelowna flights
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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 2,558,603 searches. Data last updated June 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$140 | Average$468 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$342 | Average$450 | FlexibilityNo cancel fee | On-time75% |