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Cheap flights from Kelowna to Chicago from C$ 225

YLW — CHI
9 Oct — 16 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Kelowna to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Kelowna to Chicago

Thu 24/97:50 a.m. -
1 stop6h 50m
Mon 28/95:30 p.m. -
1 stop6h 35m
Deal found 8/9C$ 316
Thu 22/1010:50 p.m. -
1 stop8h 10m
Tue 27/103:30 p.m. -
1 stop17h 43m
Deal found 9/9C$ 336
Wed 28/108:20 p.m. -
1 stop16h 17m
Sun 8/113:30 p.m. -
1 stop8h 58m
Deal found 8/9C$ 346
Sat 17/1010:50 p.m. -
1 stop8h 10m
Wed 21/102:15 p.m. -
1 stop9h 37m
Deal found 5/9C$ 389
Thu 22/106:05 a.m. -
1 stop8h 35m
Tue 27/107:00 a.m. -
1 stop7h 57m
Deal found 8/9C$ 394
Sat 17/106:05 a.m. -
2 stops9h 55m
Wed 21/101:27 p.m. -
2 stops10h 38m
Deal found 5/9C$ 473
Thu 22/106:05 a.m. -
2 stops9h 55m
Tue 27/1012:27 p.m. -
2 stops12h 58m
Deal found 9/9C$ 738
Thu 24/912:50 p.m. -
2 stops23h 45m
Mon 28/93:20 p.m. -
2 stops22h 35m
Deal found 6/9C$ 1,188
Thu 24/912:50 p.m. -
2 stops20h 10m
Mon 28/93:20 p.m. -
3 stops24h 00m
Deal found 6/9C$ 1,238
Tue 22/128:25 p.m. -
2 stops10h 48m
Sat 2/16:20 p.m. -
2 stops27h 05m
Deal found 8/9C$ 1,307

Find flight deals from Kelowna to Chicago

Round-trip from

C$ 316

One-way from

C$ 225

Popular in

December

Cheapest in

May

Average price

C$ 966
WestJet
  • WestJet
  • 24/9-28/9
  • 2 total stops
  • 13h 25m total
  • Kelowna to Chicago
Search Deals
Air Canada
  • Air Canada
  • 21/10-31/12
  • 1 total stop
  • 8h 10m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 57% potential increase in price (C$ 1,437 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 17% potential price decrease (C$ 161 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2026
Search Deals

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Kelowna to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Wed 21/10

10:50 p.m.-9:00 a.m.

1 stop8h 10m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 225

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Wed 21/10

8:45 p.m.-4:40 p.m.

3 stops17h 55m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 274

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Wed 7/10

8:15 p.m.-5:45 p.m.

2 stops19h 30m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 336

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Thu 22/10

10:50 p.m.-9:00 a.m.

1 stop8h 10m

Chicago O'Hare Intl

Tue 27/10

3:30 p.m.-7:13 a.m.

1 stop17h 43m

C$ 336

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Wed 7/10

5:55 a.m.-5:17 a.m.

3 stops21h 22m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 357

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Wed 21/10

8:15 p.m.-5:45 p.m.

2 stops19h 30m

Chicago Midway

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 374

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Sat 17/10

10:50 p.m.-9:00 a.m.

1 stop8h 10m

Chicago O'Hare Intl

Wed 21/10

2:15 p.m.-9:52 p.m.

1 stop9h 37m

C$ 390

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Thu 22/10

6:05 a.m.-4:40 p.m.

1 stop8h 35m

Chicago O'Hare Intl

Tue 27/10

7:00 a.m.-12:57 p.m.

1 stop7h 57m

C$ 394

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sat 17/10

6:05 a.m.-6:00 p.m.

2 stops9h 55m

Chicago Midway

Wed 21/10

1:27 p.m.-10:05 p.m.

2 stops10h 38m

C$ 473

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Thu 22/10

6:05 a.m.-8:30 p.m.

2 stops12h 25m

Chicago O'Hare Intl

Tue 27/10

6:20 a.m.-2:30 p.m.

2 stops10h 10m

C$ 485

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

Best time to book a flight from Kelowna to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Kelowna with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Kelowna to Chicago

What’s the top layover airport for flights from Kelowna to Chicago?

Calgary (YYC) – chosen by Cheapflights users on 50% of one-stop itineraries from Kelowna to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Kelowna to Chicago?

Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 531.

What’s the fastest layover option from Kelowna to Chicago?

Flights via Calgary (YYC) have the shortest average one-way travel time for 1-stop routes: 7h 17m.

Which airport typically offers the quickest layover for flights from Kelowna to Chicago?

Flights via Calgary (YYC) offer the fastest connection on this route, with an average layover time of 2h 01m.

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Kelowna to Chicago, such as WestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,447 reviews
Check prices

Comfort

7.1

Overall

7.2

Entertainment

6.1

Food

6.2

Crew

7.9

Boarding

7.4

Reviews

1 / 20
4.0
Okay

Jason,Jan 2024

YLW - YYC

very large man sitting in middle seat exit row. He took up 15-20% of my seat with his arms, shoulders, and leg for the entire flight and was resistant when I nudged back trying to reclaim my personal space. This resulted in an uncomfortable ride using only a fraction of the seat I paid for. I feel like I did not get the full use of the seat that I contractually should have been provided.
WestJet
7.2
Good
3,447 reviews
WestJet
7.2
Good
3,447 reviews
Check prices

Comfort

7.1

Overall

7.2

Entertainment

6.1

Food

6.2

Crew

7.9

Boarding

7.4

Reviews

1 / 20
4.0
Okay

Jason,Jan 2024

YLW - YYC

very large man sitting in middle seat exit row. He took up 15-20% of my seat with his arms, shoulders, and leg for the entire flight and was resistant when I nudged back trying to reclaim my personal space. This resulted in an uncomfortable ride using only a fraction of the seat I paid for. I feel like I did not get the full use of the seat that I contractually should have been provided.

Related info for your journey

  • What airport do you fly from for flights from Kelowna to Chicago?

    Located just 11.2 km from the city centre, Kelowna is the airport most travellers will use when flying to Chicago from Kelowna. Booking flights from Kelowna (YLW) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 0 different airlines.

  • How long is the flight from Kelowna to Chicago?

    Departing from Kelowna to Chicago will take you 8h 10m. There are 2565 km between Kelowna and Chicago. Both multi-stop and direct flights can be found to your destination and back.

  • Can I find deals for flights from Kelowna to Chicago that include hotel bookings?

    Yes. In addition to deals on Kelowna to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kelowna to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kelowna to Chicago.

  • Can I find deals for business class flights from Kelowna to Chicago?

    Yes. Cheapflights offers flight deals from Kelowna to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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