$179+ 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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YLW
Jul 23 — Jul 301
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Kelowna with Cheapflights
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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 23, 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 23, 2026.
This Trip.com deal was found by Cheapflights users on 6/18. 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.
Wed 10/216:00 am
ORD
- YLW
1 stop8h 57m
Multiple Airlines
Mon 10/265:20 am
YLW
- ORD
1 stop6h 15m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$359
This Justfly.com deal was found by Cheapflights users on 6/21. 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.
Thu 9/245:30 pm
ORD
- YLW
1 stop8h 20m
WestJet
Mon 9/286:05 am
YLW
- ORD
1 stop8h 35m
WestJet
Deal found 6/21![WestJet logo]()
$369
This FlightHub deal was found by Cheapflights users on 6/19. 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 10/15:30 pm
ORD
- YLW
1 stop6h 35m
WestJet
Mon 10/57:50 am
YLW
- ORD
1 stop6h 50m
WestJet
Deal found 6/19![WestJet logo]()
$371
This Trip.com deal was found by Cheapflights users on 6/18. 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.
Sat 8/85:30 pm
ORD
- YLW
1 stop6h 35m
WestJet
Sat 8/157:50 am
YLW
- ORD
1 stop6h 50m
WestJet
Deal found 6/18![WestJet logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 9/47:00 am
ORD
- YLW
2 stops14h 00m
Multiple Airlines
Sun 9/67:50 am
YLW
- ORD
1 stop6h 50m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$417
This Air Canada deal was found by Cheapflights users on 6/22. 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 9/283:40 pm
ORD
- YLW
1 stop9h 47m
Air Canada
Thu 10/15:25 am
YLW
- ORD
1 stop7h 18m
Air Canada
Deal found 6/22![Air Canada logo]()
$424
This Air Canada deal was found by Cheapflights users on 6/18. 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 9/303:40 pm
ORD
- YLW
1 stop9h 32m
Air Canada
Mon 10/511:30 pm
YLW
- ORD
1 stop7h 30m
Air Canada
Deal found 6/18![Air Canada logo]()
$429
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 9/245:30 pm
ORD
- YLW
1 stop6h 35m
Multiple Airlines
Mon 9/288:15 pm
YLW
- ORD
2 stops13h 47m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$430
This Air Canada deal was found by Cheapflights users on 6/21. 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 10/13:40 pm
ORD
- YLW
1 stop9h 32m
Air Canada
Mon 10/56:05 pm
YLW
- ORD
2 stops12h 55m
Air Canada
Deal found 6/21![Air Canada logo]()
$434
This Mytrip deal was found by Cheapflights users on 6/20. 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 7/710:25 am
MDW
- YLW
3 stops22h 35m
Multiple Airlines
Tue 7/1412:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$623
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 8/1310:20 am
MDW
- YLW
1 stop13h 32m
Multiple Airlines
Mon 8/178:15 pm
YLW
- MDW
2 stops16h 20m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$634
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 8/1310:20 am
MDW
- YLW
1 stop13h 32m
Porter Airlines
Mon 8/1710:50 pm
YLW
- MDW
1 stop13h 45m
Porter Airlines
Deal found 6/22![Porter 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 23, 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 23, 2026.
This Justfly.com deal was found by Cheapflights users on 6/21. 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.
Thu 9/245:30 pm
ORD
- YLW
1 stop8h 20m
WestJet
Mon 9/286:05 am
YLW
- ORD
1 stop8h 35m
WestJet
Deal found 6/21![WestJet logo]()
$369
This Air Canada deal was found by Cheapflights users on 6/22. 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 9/283:40 pm
ORD
- YLW
1 stop9h 47m
Air Canada
Thu 10/15:25 am
YLW
- ORD
1 stop7h 18m
Air Canada
Deal found 6/22![Air Canada logo]()
$424
This Mytrip deal was found by Cheapflights users on 6/20. 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 9/245:30 pm
ORD
- YLW
1 stop6h 35m
Multiple Airlines
Mon 9/285:05 am
YLW
- ORD
3 stops11h 28m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$463
This Delta deal was found by Cheapflights users on 6/22. 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 9/41:59 pm
ORD
- YLW
2 stops11h 51m
Delta
Sun 9/66:05 am
YLW
- ORD
1 stop8h 35m
Delta
Deal found 6/22![Delta logo]()
$510
This United Airlines deal was found by Cheapflights users on 6/21. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/285:00 am
ORD
- YLW
2 stops9h 17m
United Airlines
Thu 10/15:25 am
YLW
- ORD
1 stop7h 18m
United Airlines
Deal found 6/21![United Airlines logo]()
$516
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 8/1310:20 am
MDW
- YLW
1 stop13h 32m
Porter Airlines
Mon 8/1710:50 pm
YLW
- MDW
1 stop13h 45m
Porter Airlines
Deal found 6/22![Porter Airlines logo]()
$639
This FlightHub deal was found by Cheapflights users on 6/19. 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 8/65:30 pm
ORD
- YLW
1 stop8h 20m
WestJet
Mon 8/108:15 pm
YLW
- ORD
1 stop18h 25m
WestJet
Deal found 6/19![WestJet logo]()
$455
This Air Canada deal was found by Cheapflights users on 6/19. 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 7/143:45 pm
ORD
- YLW
1 stop8h 16m
Air Canada
Fri 7/1711:00 pm
YLW
- ORD
1 stop8h 00m
Air Canada
Deal found 6/19![Air Canada logo]()
$499
This United Airlines deal was found by Cheapflights users on 6/20. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:35 pm
ORD
- YLW
2 stops10h 37m
United Airlines
Sat 9/265:25 am
YLW
- ORD
1 stop7h 18m
United Airlines
Deal found 6/20![United Airlines logo]()
$516
This Justfly.com deal was found by Cheapflights users on 6/18. 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.
Mon 10/55:30 pm
ORD
- YLW
1 stop6h 35m
Multiple Airlines
Wed 10/71:47 pm
YLW
- ORD
1 stop8h 12m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$520
This Delta deal was found by Cheapflights users on 6/22. 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 10/111:17 am
ORD
- YLW
2 stops12h 48m
Delta
Mon 10/56:05 am
YLW
- ORD
2 stops12h 25m
Delta
Deal found 6/22![Delta logo]()
$525
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 8/1310:20 am
MDW
- YLW
1 stop13h 32m
Multiple Airlines
Mon 8/178:15 pm
YLW
- MDW
2 stops16h 20m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$634
This Delta deal was found by Cheapflights users on 6/22. 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 9/241:19 pm
MDW
- YLW
2 stops10h 46m
Delta
Mon 9/288:15 pm
YLW
- MDW
2 stops13h 40m
Delta
Deal found 6/22![Delta logo]()
$711
This Mytrip deal was found by Cheapflights users on 6/20. 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 7/710:25 am
MDW
- YLW
2 stops27h 30m
Porter Airlines
Tue 7/1412:50 pm
YLW
- MDW
2 stops18h 50m
Porter Airlines
Deal found 6/20![Porter Airlines logo]()
$849
This Mytrip deal was found by Cheapflights users on 6/18. 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 7/221:18 pm
MDW
- YLW
3 stops24h 37m
Multiple Airlines
Sun 7/2612:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$762
This Mytrip deal was found by Cheapflights users on 6/22. 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 9/41:25 pm
MDW
- YLW
3 stops31h 05m
WestJet
Sun 9/68:15 pm
YLW
- MDW
3 stops14h 24m
WestJet
Deal found 6/22![WestJet logo]()
$860
This Mytrip deal was found by Cheapflights users on 6/20. 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 7/710:25 am
MDW
- YLW
3 stops15h 25m
Multiple Airlines
Tue 7/145:05 am
YLW
- MDW
3 stops31h 30m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$773
This Mytrip deal was found by Cheapflights users on 6/19. 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 7/179:19 am
MDW
- YLW
3 stops28h 36m
Multiple Airlines
Fri 7/2412:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$794
This Mytrip deal was found by Cheapflights users on 6/22. 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 9/46:42 pm
MDW
- YLW
3 stops20h 38m
Multiple Airlines
Sun 9/610:50 pm
YLW
- MDW
2 stops11h 49m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$927
Last-minute flights from Chicago to KelownaDiscover last-minute flight deals from Chicago to Kelowna. Data last updated June 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kelowna. Data last updated June 23, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 6/20. 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.
Tue 7/77:15 am
ORD
- YLW
2 stops14h 50m
Multiple Airlines
Tue 7/148:15 pm
YLW
- ORD
1 stop18h 25m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$516
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 7/75:30 pm
ORD
- YLW
1 stop8h 20m
WestJet
Tue 7/146:30 pm
YLW
- ORD
1 stop20h 10m
WestJet
Deal found 6/21![WestJet logo]()
$564
This Mytrip deal was found by Cheapflights users on 6/20. 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 7/710:25 am
MDW
- YLW
3 stops22h 35m
Multiple Airlines
Tue 7/1412:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$623
This Mytrip deal was found by Cheapflights users on 6/21. 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 7/710:25 am
MDW
- YLW
3 stops22h 35m
Multiple Airlines
Sun 7/125:55 am
YLW
- MDW
3 stops25h 45m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$785
This Air Canada deal was found by Cheapflights users on 6/21. 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 7/143:45 pm
ORD
- YLW
1 stop8h 16m
Air Canada
Fri 7/1711:00 pm
YLW
- ORD
1 stop8h 00m
Air Canada
Deal found 6/21![Air Canada logo]()
$499
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 7/175:30 pm
ORD
- YLW
1 stop6h 35m
Multiple Airlines
Fri 7/247:50 pm
YLW
- ORD
2 stops19h 14m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$530
This Mytrip deal was found by Cheapflights users on 6/19. 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 7/179:19 am
MDW
- YLW
3 stops28h 36m
Multiple Airlines
Fri 7/2412:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$794
This oojo deal was found by Cheapflights users on 6/22. 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.
Mon 7/205:30 pm
ORD
- YLW
1 stop6h 35m
WestJet
Wed 7/226:05 am
YLW
- ORD
1 stop8h 35m
WestJet
Deal found 6/22![WestJet logo]()
$446
This FlightHub deal was found by Cheapflights users on 6/22. 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.
Mon 7/205:30 pm
ORD
- YLW
1 stop8h 20m
Multiple Airlines
Wed 7/221:46 pm
YLW
- ORD
1 stop8h 13m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$461
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 7/215:30 pm
ORD
- YLW
1 stop6h 35m
Multiple Airlines
Fri 7/247:50 pm
YLW
- ORD
2 stops19h 14m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$531
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 7/225:30 pm
ORD
- YLW
1 stop6h 35m
Multiple Airlines
Sun 7/267:50 pm
YLW
- ORD
2 stops37h 34m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$514
This Mytrip deal was found by Cheapflights users on 6/18. 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 7/221:18 pm
MDW
- YLW
3 stops24h 37m
Multiple Airlines
Sun 7/2612:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$762
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 23, 2026.
Search for one-way flight options from Chicago to Kelowna. Find affordable one-way fares based on user searches. Data last updated June 23, 2026.
This Air Canada deal was found by Cheapflights users on 6/18. 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 11/123:40 pm
ORD
- YLW
1 stop9h 38m
Air Canada
Deal found 6/18![Air Canada logo]()
$179
This Air Canada deal was found by Cheapflights users on 6/18. 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 11/149:50 am
ORD
- YLW
2 stops12h 44m
Air Canada
Deal found 6/18![Air Canada logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 8/199:20 pm
ORD
- YLW
3 stops28h 10m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$202
This oojo deal was found by Cheapflights users on 6/21. 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.
Fri 8/145:30 pm
ORD
- YLW
1 stop8h 20m
WestJet
Deal found 6/21![WestJet logo]()
$204
This Air Canada deal was found by Cheapflights users on 6/19. 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 8/193:45 pm
ORD
- YLW
1 stop8h 16m
Air Canada
Deal found 6/19![Air Canada logo]()
$226
This Air Canada deal was found by Cheapflights users on 6/18. 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 7/183:50 pm
ORD
- YLW
1 stop8h 11m
Air Canada
Deal found 6/18![Air Canada logo]()
$228
This Trip.com deal was found by Cheapflights users on 6/19. 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.
Sun 8/99:50 am
ORD
- YLW
3 stops16h 00m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 7/279:13 pm
ORD
- YLW
3 stops24h 52m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$234
This Alaska Airlines deal was found by Cheapflights users on 6/18. 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.
Sun 11/157:00 am
ORD
- YLW
1 stop9h 46m
Alaska Airlines
Deal found 6/18![Alaska Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 8/910:20 am
MDW
- YLW
3 stops15h 30m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$245
This FlightHub deal was found by Cheapflights users on 6/19. 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 8/195:30 pm
ORD
- YLW
2 stops32h 00m
WestJet
Deal found 6/19![WestJet logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 7/276:05 am
MDW
- YLW
2 stops19h 45m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$251
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 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $359 (Trip.com) |
One-way from | $179 (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 23, 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
Thu 9/24
5:30 pm-11:50 pm
1 stop8h 20m
Kelowna
Mon 9/28
6:05 am-4:40 pm
1 stop8h 35m
$369
ChicagoKelowna
ORD - YLW
ORDYLW
Chicago O'Hare Intl
Mon 9/28
3:40 pm-11:27 pm
1 stop9h 47m
Kelowna
Thu 10/1
5:25 am-2:43 pm
1 stop7h 18m
$424
ChicagoKelowna
ORD - YLW
ORDYLW
Chicago O'Hare Intl
Thu 8/6
5:30 pm-11:50 pm
1 stop8h 20m
Kelowna
Mon 8/10
8:15 pm-4:40 pm
1 stop18h 25m
$455
ChicagoKelowna
ORD - YLW
ORDYLW
Chicago O'Hare Intl
Thu 9/24
5:30 pm-10:05 pm
1 stop6h 35m
Kelowna
Mon 9/28
5:05 am-6:33 pm
3 stops11h 28m
$463
ChicagoKelowna
ORD - YLW
ORDYLW
Chicago O'Hare Intl
Tue 7/14
3:45 pm-10:01 pm
1 stop8h 16m
Kelowna
Fri 7/17
11:00 pm-9:00 am
1 stop8h 00m
$499
ChicagoKelowna
ORD - YLW
ORDYLW
Chicago O'Hare Intl
Fri 9/4
1:59 pm-11:50 pm
2 stops11h 51m
Kelowna
Sun 9/6
6:05 am-4:40 pm
1 stop8h 35m
$510
ChicagoKelowna
ORD - YLW
ORDYLW
Chicago O'Hare Intl
Mon 9/28
5:00 am-12:17 pm
2 stops9h 17m
Kelowna
Thu 10/1
5:25 am-2:43 pm
1 stop7h 18m
$516
ChicagoKelowna
ORD - YLW
ORDYLW
Chicago O'Hare Intl
Sat 9/19
2:35 pm-11:12 pm
2 stops10h 37m
Kelowna
Sat 9/26
5:25 am-2:43 pm
1 stop7h 18m
$516
Quickest round-trip
ChicagoKelowna
ORD - YLW
ORDYLW
Chicago O'Hare Intl
Mon 10/5
5:30 pm-10:05 pm
1 stop6h 35m
Kelowna
Wed 10/7
1:47 pm-11:59 pm
1 stop8h 12m
$520
ChicagoKelowna
ORD - YLW
ORDYLW
Chicago O'Hare Intl
Thu 10/1
11:17 am-10:05 pm
2 stops12h 48m
Kelowna
Mon 10/5
6:05 am-8:30 pm
2 stops12h 25m
$525
Showing 1-10 of 39 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
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
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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 June 23, 2026.
Chicago and Kelowna flights
Browse other Chicago and Kelowna flight options. Last updated on June 23, 2026.
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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 23, 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% |