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Cheap flights from Kelowna to Chicago from C$ 291

YLW — CHI
4 Dec — 11 Dec1
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

Tue 1/122:28 p.m. -
1 stop8h 31m
Tue 8/123:19 p.m. -
1 stop8h 18m
Deal found 31/10C$ 506
Sat 21/119:25 p.m. -
1 stop16h 12m
Sun 6/123:30 p.m. -
1 stop8h 03m
Deal found 1/11C$ 552
Thu 26/1110:15 a.m. -
1 stop5h 55m
Sun 29/118:49 a.m. -
1 stop12h 38m
Deal found 30/10C$ 613
Sat 21/1112:05 p.m. -
2 stops10h 54m
Sun 6/123:30 p.m. -
1 stop8h 03m
Deal found 1/11C$ 622
Thu 26/1112:05 p.m. -
2 stops23h 10m
Sun 29/118:49 a.m. -
1 stop14h 39m
Deal found 31/10C$ 638
Tue 15/122:28 p.m. -
1 stop8h 31m
Tue 22/128:59 p.m. -
1 stop27h 49m
Deal found 30/10C$ 652

Find flight deals from Kelowna to Chicago

Round-trip from

C$ 506

One-way from

C$ 291

Popular in

October

Cheapest in

May

Average price

C$ 780
Alaska Airlines
  • Alaska Airlines
  • 1/12-8/12
  • 2 total stops
  • 16h 49m total
  • Kelowna to Chicago
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Alaska Airlines
  • Alaska Airlines
  • 21/11-31/12
  • 1 total stop
  • 8h 37m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 201 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease (C$ 53 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2026
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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

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Wed 16/12

6:05 a.m.-12:54 a.m.

3 stops17h 49m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 329

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Sat 21/11

5:50 a.m.-11:59 p.m.

2 stops17h 09m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 345

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Fri 18/12

12:40 p.m.-9:34 a.m.

2 stops19h 54m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 394

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Sat 21/11

6:45 p.m.-11:00 a.m.

3 stops39h 15m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 399

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Fri 18/12

12:40 p.m.-12:57 a.m.

3 stops35h 17m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 464

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Tue 1/12

2:28 p.m.-11:59 p.m.

1 stop8h 31m

Chicago O'Hare Intl

Tue 8/12

3:19 p.m.-10:37 p.m.

1 stop8h 18m

C$ 506

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Tue 26/1

5:50 a.m.-2:32 p.m.

1 stop7h 42m

Chicago O'Hare Intl

Wed 27/1

3:35 p.m.-10:28 p.m.

1 stop7h 53m

C$ 509
Quickest round-trip

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Fri 18/12

8:00 a.m.-8:01 p.m.

1 stop11h 01m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 599

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Tue 12/1

5:50 a.m.-2:32 p.m.

1 stop7h 42m

Chicago O'Hare Intl

Tue 12/1

8:15 p.m.-8:27 p.m.

2 stops25h 12m

C$ 636

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Thu 26/11

3:55 p.m.-5:01 a.m.

2 stops12h 06m

Chicago O'Hare Intl

Sun 29/11

8:49 a.m.-8:27 p.m.

1 stop12h 38m

C$ 636

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 14 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?

Seattle (SEA) – chosen by Cheapflights users on 67% 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$ 275.

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: 6h 50m.

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 1h 48m.

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Kelowna to Chicago, such as WestJet and Air Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,441 reviews
Check prices

Crew

7.9

Comfort

7.1

Overall

7.2

Entertainment

6.1

Food

6.2

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
3,441 reviews
WestJet
7.2
Good
3,441 reviews
Check prices

Crew

7.9

Comfort

7.1

Overall

7.2

Entertainment

6.1

Food

6.2

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.
Air Canada
7.1
Good
11,859 reviews
WestJet
7.2
Good
3,441 reviews
Check prices

Crew

7.9

Comfort

7.1

Overall

7.2

Entertainment

6.1

Food

6.2

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 1 airline.

  • How long is the flight from Kelowna to Chicago?

    Departing from Kelowna to Chicago will take you 7h 42m. There are 2565 km between Kelowna and Chicago. Both multi-stop and direct flights can be found to your destination and back.

  • What is the cheapest airline to fly from Kelowna to Chicago round-trip?

    Cheapflights users have booked flights from Kelowna to Chicago round-trip from C$ 531. Air Canada is currently priced 21% below the average price you’ll pay for this route.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Top airline flying from Kelowna to Chicago

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 531AverageC$ 710FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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