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Cheap flights from Kelowna to Chicago from C$ 210

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 28/8. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — CHI
17 Aug — 24 Aug1
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
Explore the most affordable flight options available from Kelowna to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 18 July 2026.

Fri 25/97:50 a.m.
YLW
-
ORD
1 stop6h 50m
WestJet
Mon 28/95:30 p.m.
ORD
-
YLW
1 stop19h 45m
WestJet
Deal found 16/7C$ 496
Fri 18/95:25 a.m.
YLW
-
ORD
1 stop7h 18m
Air Canada
Tue 22/92:15 p.m.
ORD
-
YLW
1 stop9h 42m
Air Canada
Deal found 13/7C$ 510
Sat 10/105:25 a.m.
YLW
-
ORD
1 stop7h 18m
Air Canada
Sun 11/103:40 p.m.
ORD
-
YLW
1 stop9h 32m
Air Canada
Deal found 15/7C$ 523
Wed 9/95:25 a.m.
YLW
-
ORD
1 stop7h 18m
Air Canada
Sat 12/93:40 p.m.
ORD
-
YLW
1 stop9h 07m
Air Canada
Deal found 16/7C$ 565
Thu 6/811:00 p.m.
YLW
-
ORD
1 stop8h 00m
Air Canada
Tue 8/93:40 p.m.
ORD
-
YLW
1 stop9h 47m
Air Canada
Deal found 15/7C$ 581
Sat 26/910:50 p.m.
YLW
-
ORD
1 stop8h 10m
United Airlines
Mon 28/95:00 a.m.
ORD
-
YLW
2 stops9h 17m
United Airlines
Deal found 16/7C$ 589
Fri 18/96:05 a.m.
YLW
-
MDW
2 stops10h 28m
Delta
Tue 22/99:59 a.m.
MDW
-
YLW
2 stops11h 01m
Delta
Deal found 13/7C$ 941
Sat 26/96:05 a.m.
YLW
-
MDW
2 stops10h 15m
Delta
Mon 28/91:19 p.m.
MDW
-
YLW
2 stops10h 46m
Delta
Deal found 16/7C$ 1,041
Fri 25/912:50 p.m.
YLW
-
MDW
2 stops23h 45m
Porter Airlines
Mon 28/93:20 p.m.
MDW
-
YLW
2 stops22h 35m
Porter Airlines
Deal found 16/7C$ 1,083
Sat 10/106:30 p.m.
YLW
-
MDW
2 stops13h 22m
WestJet
Sun 11/101:28 p.m.
MDW
-
YLW
2 stops10h 37m
WestJet
Deal found 15/7C$ 1,179
Thu 30/78:15 p.m.
YLW
-
MDW
2 stops11h 50m
WestJet
Mon 24/81:25 p.m.
MDW
-
YLW
2 stops10h 40m
WestJet
Deal found 15/7C$ 1,188
Sat 26/97:50 a.m.
YLW
-
MDW
3 stops28h 45m
Multiple Airlines
Mon 28/99:29 a.m.
MDW
-
YLW
3 stops12h 36m
Multiple Airlines
Deal found 16/7C$ 1,203

Find flight deals from Kelowna to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Kelowna (YLW) to Chicago (CHI). 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 18 July 2026.

Round-trip from

C$ 496

One-way from

C$ 210

Popular in

September

Cheapest in

May

Average price

C$ 676
WestJet
  • WestJet
  • 25/9-28/9
  • 2 total stops
  • 26h 35m total
  • Kelowna to Chicago
Search Deals
WestJet
  • WestJet
  • 28/8
  • 1 total stop
  • 8h 35m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 193 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 60 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kelowna to Chicago 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 629,999 searches. Data last updated 18 July 2026.
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 - ORD

YLWORD

Kelowna

Fri 25/9

7:50 a.m.-4:40 p.m.

1 stop6h 50m

Chicago O'Hare Intl

Mon 28/9

5:30 p.m.-11:15 a.m.

1 stop19h 45m

C$ 496
Quickest round-trip

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 9/9

5:25 a.m.-2:43 p.m.

1 stop7h 18m

Chicago O'Hare Intl

Sat 12/9

3:40 p.m.-10:47 p.m.

1 stop9h 07m

C$ 565

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 6/8

11:00 p.m.-9:00 a.m.

1 stop8h 00m

Chicago O'Hare Intl

Tue 8/9

3:40 p.m.-11:27 p.m.

1 stop9h 47m

C$ 581

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 18/9

5:25 a.m.-2:43 p.m.

1 stop7h 18m

Chicago O'Hare Intl

Tue 22/9

5:00 a.m.-12:17 p.m.

2 stops9h 17m

C$ 582

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sat 26/9

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

1 stop8h 10m

Chicago O'Hare Intl

Mon 28/9

5:00 a.m.-12:17 p.m.

2 stops9h 17m

C$ 589

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sat 10/10

5:25 a.m.-2:43 p.m.

1 stop7h 18m

Chicago O'Hare Intl

Sun 11/10

5:00 a.m.-2:12 p.m.

2 stops11h 12m

C$ 642

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 9/9

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

2 stops12h 25m

Chicago O'Hare Intl

Sat 12/9

2:00 p.m.-10:05 p.m.

2 stops10h 05m

C$ 647

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 6/8

11:00 p.m.-9:00 a.m.

1 stop8h 00m

Chicago O'Hare Intl

Tue 8/9

10:00 p.m.-12:17 p.m.

2 stops16h 17m

C$ 668

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 18/9

6:05 a.m.-6:33 p.m.

2 stops10h 28m

Chicago Midway

Tue 22/9

9:59 a.m.-7:00 p.m.

2 stops11h 01m

C$ 941

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sat 26/9

6:05 a.m.-6:20 p.m.

2 stops10h 15m

Chicago Midway

Mon 28/9

1:19 p.m.-10:05 p.m.

2 stops10h 46m

C$ 1,041

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/7

Showing 1-10 of 19 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
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 Kelowna to Chicago

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

Share of one-stop round-trip flights from Kelowna to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Seattle (SEA) – chosen by Cheapflights users on 60% of one-stop itineraries from Kelowna to Chicago on Cheapflights.

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

Average round-trip fare for 1-stop flights from Kelowna to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 540.

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

Shortest average travel time for 1-stop one-way flights from Kelowna to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

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?

Average layover duration for 1-stop one-way flights from Kelowna to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

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

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 18 July 2026.
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
3,411 reviews
Check prices

Entertainment

6.1

Overall

7.2

Comfort

7.0

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
3,411 reviews
WestJet
7.2
Good
3,411 reviews
Check prices

Entertainment

6.1

Overall

7.2

Comfort

7.0

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.
Air Canada
7.1
Good
11,352 reviews
WestJet
7.2
Good
3,411 reviews
Check prices

Entertainment

6.1

Overall

7.2

Comfort

7.0

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

Find useful and relevant information for your journey from Kelowna to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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 6h 50m. 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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