$202+ 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 6/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YLW
Jun 7 — Jun 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 May 8, 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 May 8, 2026.
This FlightHub deal was found by Cheapflights users on 5/4. 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.
Tue 6/25:30 pm
ORD
- YLW
1 stop8h 20m
Multiple Airlines
Tue 6/93:36 pm
YLW
- ORD
2 stops11h 24m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$410
This FlightHub deal was found by Cheapflights users on 5/4. 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.
Tue 6/25:30 pm
ORD
- YLW
1 stop8h 20m
WestJet
Tue 6/912:05 pm
YLW
- ORD
1 stop26h 35m
WestJet
Deal found 5/4![WestJet logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/85:30 pm
ORD
- YLW
2 stops24h 15m
WestJet
Fri 6/127:50 am
YLW
- ORD
1 stop6h 50m
WestJet
Deal found 5/3![WestJet logo]()
$419
This oojo deal was found by Cheapflights users on 5/3. 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 oojo 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 8/168:45 pm
YLW
- ORD
2 stops17h 55m
WestJet
Deal found 5/3![WestJet logo]()
$444
This Air Canada deal was found by Cheapflights users on 5/3. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:40 pm
ORD
- YLW
1 stop9h 32m
Air Canada
Tue 9/295:25 am
YLW
- ORD
1 stop7h 23m
Air Canada
Deal found 5/3![Air Canada logo]()
$465
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/155:30 pm
ORD
- YLW
1 stop6h 35m
Multiple Airlines
Mon 6/225:20 pm
YLW
- ORD
2 stops29h 28m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$498
This Mytrip deal was found by Cheapflights users on 5/5. 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 6/1910:25 am
MDW
- YLW
3 stops22h 35m
Multiple Airlines
Fri 6/2612:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$697
This Mytrip deal was found by Cheapflights users on 5/4. 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.
Fri 7/241:49 pm
MDW
- YLW
3 stops21h 51m
Multiple Airlines
Sun 7/2612:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$830
This Mytrip deal was found by Cheapflights users on 5/4. 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 6/29:22 am
MDW
- YLW
3 stops16h 08m
Multiple Airlines
Tue 6/912:50 pm
YLW
- MDW
2 stops18h 45m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$883
This Mytrip deal was found by Cheapflights users on 5/4. 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 6/29:22 am
MDW
- YLW
3 stops16h 08m
WestJet
Tue 6/96:30 pm
YLW
- MDW
3 stops16h 39m
WestJet
Deal found 5/4![WestJet logo]()
$973
This Mytrip deal was found by Cheapflights users on 5/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/219:17 am
MDW
- YLW
3 stops12h 48m
Multiple Airlines
Sun 6/2812:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$981
This Mytrip deal was found by Cheapflights users on 5/4. 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.
Fri 7/249:19 am
MDW
- YLW
3 stops12h 06m
WestJet
Sun 7/265:05 am
YLW
- MDW
3 stops11h 20m
WestJet
Deal found 5/4![WestJet logo]()
$1,033
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 May 8, 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 May 8, 2026.
This Trip.com deal was found by Cheapflights users on 5/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/85:30 pm
ORD
- YLW
1 stop21h 50m
WestJet
Fri 6/126:05 am
YLW
- ORD
1 stop8h 35m
WestJet
Deal found 5/3![WestJet logo]()
$410
This Air Canada deal was found by Cheapflights users on 5/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/203:40 pm
ORD
- YLW
1 stop9h 32m
Air Canada
Sat 10/245:25 am
YLW
- ORD
1 stop7h 23m
Air Canada
Deal found 5/7![Air Canada logo]()
$486
This Mytrip deal was found by Cheapflights users on 5/5. 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 6/199:17 am
MDW
- YLW
2 stops27h 30m
Multiple Airlines
Fri 6/2612:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$788
This FlightHub deal was found by Cheapflights users on 5/4. 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.
Tue 6/25:30 pm
ORD
- YLW
1 stop8h 20m
WestJet
Tue 6/912:05 pm
YLW
- ORD
1 stop26h 35m
WestJet
Deal found 5/4![WestJet logo]()
$414
This Delta deal was found by Cheapflights users on 5/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:27 pm
MDW
- YLW
2 stops10h 38m
Delta
Sun 8/166:05 am
YLW
- MDW
2 stops10h 28m
Delta
Deal found 5/3![Delta logo]()
$1,066
This oojo deal was found by Cheapflights users on 5/7. 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.
Tue 8/115:30 pm
ORD
- YLW
1 stop8h 20m
WestJet
Sun 8/168:45 pm
YLW
- ORD
2 stops17h 55m
WestJet
Deal found 5/7![WestJet logo]()
$486
This Mytrip deal was found by Cheapflights users on 5/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/219:17 am
MDW
- YLW
3 stops12h 48m
Multiple Airlines
Sun 6/2812:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$981
This Mytrip deal was found by Cheapflights users on 5/4. 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.
Fri 7/249:19 am
MDW
- YLW
3 stops12h 06m
WestJet
Sun 7/265:05 am
YLW
- MDW
3 stops11h 20m
WestJet
Deal found 5/4![WestJet logo]()
$1,033
This oojo deal was found by Cheapflights users on 5/3. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/261:21 pm
MDW
- YLW
2 stops10h 44m
WestJet
Sun 7/56:00 am
YLW
- MDW
2 stops10h 18m
WestJet
Deal found 5/3![WestJet logo]()
$1,087
This oojo deal was found by Cheapflights users on 5/4. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:27 pm
MDW
- YLW
2 stops10h 38m
WestJet
Sun 8/166:30 pm
YLW
- MDW
2 stops13h 29m
WestJet
Deal found 5/4![WestJet logo]()
$1,091
This oojo deal was found by Cheapflights users on 5/4. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/309:49 am
MDW
- YLW
2 stops11h 36m
WestJet
Sun 8/26:30 pm
YLW
- MDW
2 stops13h 29m
WestJet
Deal found 5/4![WestJet logo]()
$1,092
This oojo deal was found by Cheapflights users on 5/3. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/159:54 am
MDW
- YLW
2 stops11h 06m
WestJet
Mon 6/225:05 am
YLW
- MDW
2 stops11h 13m
WestJet
Deal found 5/3![WestJet logo]()
$1,111
This WestJet deal was found by Cheapflights users on 5/4. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:30 am
MDW
- YLW
2 stops14h 35m
WestJet
Tue 9/294:30 pm
YLW
- MDW
2 stops23h 35m
WestJet
Deal found 5/4![WestJet logo]()
$1,205
Last-minute flights from Chicago to KelownaDiscover last-minute flight deals from Chicago to Kelowna. Data last updated May 8, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kelowna. Data last updated May 8, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 5/4. 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.
Tue 6/25:30 pm
ORD
- YLW
1 stop8h 20m
Multiple Airlines
Tue 6/93:36 pm
YLW
- ORD
2 stops11h 24m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$410
This FlightHub deal was found by Cheapflights users on 5/4. 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.
Tue 6/25:30 pm
ORD
- YLW
1 stop8h 20m
WestJet
Tue 6/912:05 pm
YLW
- ORD
1 stop26h 35m
WestJet
Deal found 5/4![WestJet logo]()
$414
This Mytrip deal was found by Cheapflights users on 5/4. 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 6/29:22 am
MDW
- YLW
3 stops16h 08m
Multiple Airlines
Tue 6/912:50 pm
YLW
- MDW
2 stops18h 45m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$883
This Mytrip deal was found by Cheapflights users on 5/4. 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 6/29:22 am
MDW
- YLW
3 stops16h 08m
WestJet
Tue 6/96:30 pm
YLW
- MDW
3 stops16h 39m
WestJet
Deal found 5/4![WestJet logo]()
$973
This Air Canada deal was found by Cheapflights users on 5/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/63:45 pm
ORD
- YLW
1 stop8h 06m
Air Canada
Sat 6/1310:50 pm
YLW
- ORD
1 stop8h 10m
Air Canada
Deal found 5/7![Air Canada logo]()
$528
This Expedia deal was found by Cheapflights users on 5/7. 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 6/66:00 am
ORD
- YLW
1 stop10h 46m
Alaska Airlines
Sat 6/131:46 pm
YLW
- ORD
2 stops13h 14m
Alaska Airlines
Deal found 5/7![Alaska Airlines logo]()
$543
This Mytrip deal was found by Cheapflights users on 5/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:30 pm
ORD
- YLW
1 stop6h 35m
Multiple Airlines
Sat 6/137:05 pm
YLW
- ORD
3 stops22h 14m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$605
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/85:30 pm
ORD
- YLW
2 stops24h 15m
WestJet
Fri 6/127:50 am
YLW
- ORD
1 stop6h 50m
WestJet
Deal found 5/3![WestJet logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/155:30 pm
ORD
- YLW
1 stop6h 35m
Multiple Airlines
Mon 6/225:20 pm
YLW
- ORD
2 stops29h 28m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$498
This Mytrip deal was found by Cheapflights users on 5/5. 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 6/1910:25 am
MDW
- YLW
3 stops22h 35m
Multiple Airlines
Fri 6/2612:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$697
This Air Canada deal was found by Cheapflights users on 5/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/217:44 pm
ORD
- YLW
1 stop16h 45m
Air Canada
Sun 6/287:25 pm
YLW
- ORD
1 stop8h 15m
Air Canada
Deal found 5/7![Air Canada logo]()
$574
This Mytrip deal was found by Cheapflights users on 5/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/219:17 am
MDW
- YLW
3 stops12h 48m
Multiple Airlines
Sun 6/2812:50 pm
YLW
- MDW
2 stops18h 50m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$981
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 May 8, 2026.
Search for one-way flight options from Chicago to Kelowna. Find affordable one-way fares based on user searches. Data last updated May 8, 2026.
This Air Canada deal was found by Cheapflights users on 5/6. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/202:15 pm
ORD
- YLW
1 stop9h 45m
Air Canada
Deal found 5/6![Air Canada logo]()
$202
This Air Canada deal was found by Cheapflights users on 5/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/217:44 pm
ORD
- YLW
1 stop16h 45m
Air Canada
Deal found 5/7![Air Canada logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/206:00 am
MDW
- YLW
2 stops53h 45m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/209:48 pm
ORD
- YLW
3 stops37h 57m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$315
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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.
Thu 6/47:49 pm
ORD
- YLW
1 stop20h 57m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$328
This United Airlines deal was found by Cheapflights users on 5/3. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:00 am
ORD
- YLW
2 stops13h 28m
United Airlines
Deal found 5/3![United Airlines logo]()
$353
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 5/1310:00 am
ORD
- YLW
3 stops15h 30m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 6/218:09 pm
ORD
- YLW
3 stops38h 11m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$364
This Travelocity deal was found by Cheapflights users on 5/5. 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.
Wed 5/137:40 am
ORD
- YLW
1 stop9h 06m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$374
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 6/218:03 pm
MDW
- YLW
3 stops36h 57m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$382
This Delta deal was found by Cheapflights users on 5/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/281:59 pm
MDW
- YLW
2 stops11h 51m
Delta
Deal found 5/3![Delta logo]()
$660
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/283:20 pm
MDW
- YLW
3 stops44h 25m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$1,780
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 May 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $410 (FlightHub) |
One-way from | $202 (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 May 8, 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 6/8
5:30 pm-1:20 pm
1 stop21h 50m
Kelowna
Fri 6/12
6:05 am-4:40 pm
1 stop8h 35m
$410
ChicagoKelowna
ORD - YLW
ORDYLW
Chicago O'Hare Intl
Tue 6/2
5:30 pm-11:50 pm
1 stop8h 20m
Kelowna
Tue 6/9
12:05 pm-4:40 pm
1 stop26h 35m
$414
Quickest round-trip
ChicagoKelowna
ORD - YLW
ORDYLW
Chicago O'Hare Intl
Tue 10/20
3:40 pm-11:12 pm
1 stop9h 32m
Kelowna
Sat 10/24
5:25 am-2:48 pm
1 stop7h 23m
$486
ChicagoKelowna
ORD - YLW
ORDYLW
Chicago O'Hare Intl
Tue 8/11
5:30 pm-11:50 pm
1 stop8h 20m
Kelowna
Sun 8/16
8:45 pm-4:40 pm
2 stops17h 55m
$486
ChicagoKelowna
MDW - YLW
MDWYLW
Chicago Midway
Fri 6/19
9:17 am-10:47 am
2 stops27h 30m
Kelowna
Fri 6/26
12:50 pm-9:40 am
2 stops18h 50m
$788
ChicagoKelowna
MDW - YLW
MDWYLW
Chicago Midway
Sun 6/21
9:17 am-8:05 pm
3 stops12h 48m
Kelowna
Sun 6/28
12:50 pm-9:40 am
2 stops18h 50m
$981
ChicagoKelowna
MDW - YLW
MDWYLW
Chicago Midway
Fri 7/24
9:19 am-7:25 pm
3 stops12h 06m
Kelowna
Sun 7/26
5:05 am-6:25 pm
3 stops11h 20m
$1,033
ChicagoKelowna
MDW - YLW
MDWYLW
Chicago Midway
Tue 8/11
1:27 pm-10:05 pm
2 stops10h 38m
Kelowna
Sun 8/16
6:05 am-6:33 pm
2 stops10h 28m
$1,066
ChicagoKelowna
MDW - YLW
MDWYLW
Chicago Midway
Fri 6/26
1:21 pm-10:05 pm
2 stops10h 44m
Kelowna
Sun 7/5
6:00 am-6:18 pm
2 stops10h 18m
$1,087
ChicagoKelowna
MDW - YLW
MDWYLW
Chicago Midway
Tue 8/11
1:27 pm-10:05 pm
2 stops10h 38m
Kelowna
Sun 8/16
6:30 pm-9:59 am
2 stops13h 29m
$1,091
Showing 1-10 of 25 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 May.
| 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 May 8, 2026.
Chicago and Kelowna flights
Browse other Chicago and Kelowna flight options. Last updated on May 8, 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 May 8, 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 May 8, 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% |