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Cheap flights from Kelowna to Chicago from C$ 329

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Kelowna to Chicago departing on 21/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Kelowna to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
6:05 a.m. - 4:40 p.m.YLW  Kelowna-ORD Chicago O'Hare Intl
8h 35m1 stop Calgary
WestJet Logo
5:30 p.m. - 11:50 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
8h 20m1 stop Calgary
C$ 417WestJet
Fri, 4 Sep - Thu, 10 Sep
Air Canada Logo
5:50 a.m. - 2:37 p.m.YLW  Kelowna-ORD Chicago O'Hare Intl
6h 47m1 stop Vancouver Intl
Air Canada Logo
3:30 p.m. - 11:28 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
8h 58m1 stop Vancouver Intl
C$ 474Air Canada
Wed, 28 Oct - Sat, 7 Nov
WestJet Logo
7:50 a.m. - 4:40 p.m.YLW  Kelowna-ORD Chicago O'Hare Intl
6h 50m1 stop Calgary
WestJet Logo
5:30 p.m. - 11:50 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
8h 20m1 stop Calgary
C$ 477WestJet
Fri, 4 Sep - Fri, 11 Sep
Air Canada Logo
5:50 a.m. - 2:37 p.m.YLW  Kelowna-ORD Chicago O'Hare Intl
6h 47m1 stop Vancouver Intl
Air Canada Logo
3:30 p.m. - 11:28 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
8h 58m1 stop Vancouver Intl
C$ 542Air Canada
Wed, 28 Oct - Sat, 7 Nov
Air Canada Logo
9:15 a.m. - 5:10 p.m.YLW  Kelowna-ORD Chicago O'Hare Intl
5h 55m1 stop Calgary
Air Canada Logo
8:40 a.m. - 7:38 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
11h 58m2 stops Calgary Vancouver Intl
C$ 557Air Canada
Wed, 28 Oct - Sat, 7 Nov
WestJet Logo
6:05 a.m. - 4:40 p.m.YLW  Kelowna-ORD Chicago O'Hare Intl
8h 35m1 stop Calgary
WestJet Logo
5:30 p.m. - 7:00 a.m.ORD  Chicago O'Hare Intl-YLW Kelowna
15h 30m2 stops Calgary Edmonton
C$ 559WestJet
Fri, 4 Sep - Fri, 11 Sep
Air Canada Logo
10:50 p.m. - 9:00 a.m.YLW  Kelowna-ORD Chicago O'Hare Intl
8h 10m1 stop Toronto Pearson Intl
Air Canada Logo
3:40 p.m. - 11:12 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
9h 32m1 stop Vancouver Intl
C$ 588Air Canada
Mon, 5 Oct - Wed, 7 Oct
Air Canada Logo
10:50 p.m. - 9:00 a.m.YLW  Kelowna-ORD Chicago O'Hare Intl
8h 10m1 stop Toronto Pearson Intl
Air Canada Logo
3:40 p.m. - 11:27 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
9h 47m1 stop Vancouver Intl
C$ 589Air Canada
Sat, 19 Sep - Sat, 26 Sep
Air Canada Logo
8:30 p.m. - 1:23 p.m.YLW  Kelowna-ORD Chicago O'Hare Intl
14h 53m2 stops Vancouver Intl Toronto Pearson Intl
Air Canada Logo
3:40 p.m. - 11:12 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
9h 32m1 stop Vancouver Intl
C$ 591Air Canada
Wed, 30 Sep - Sat, 3 Oct
Air Canada Logo
10:50 p.m. - 9:00 a.m.YLW  Kelowna-ORD Chicago O'Hare Intl
8h 10m1 stop Toronto Pearson Intl
Air Canada Logo
3:40 p.m. - 11:12 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
9h 32m1 stop Vancouver Intl
C$ 594Air Canada
Wed, 30 Sep - Sat, 3 Oct

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Delta flights from Kelowna to Chicago O'Hare Intl Airport

Our best Delta deals on Kelowna to Chicago O'Hare Intl Airport flight tickets
Delta
28 Oct
YLW8:55 a.m.Kelowna
11h 05m
2 stops
ORD10:00 p.m.Chicago O'Hare Intl
5 Nov
ORD6:20 a.m.Chicago O'Hare Intl
10h 12m
2 stops
YLW3:32 p.m.Kelowna
C$ 638
Delta
5 Oct
YLW7:50 a.m.Kelowna
6h 50m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
7 Oct
ORD1:55 p.m.Chicago O'Hare Intl
11h 55m
2 stops
YLW11:50 p.m.Kelowna
C$ 654
Delta
5 Oct
YLW7:50 a.m.Kelowna
6h 50m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
7 Oct
ORD1:55 p.m.Chicago O'Hare Intl
11h 55m
2 stops
YLW11:50 p.m.Kelowna
C$ 655

Air Canada flights from Kelowna to Chicago O'Hare Intl Airport

Our best Air Canada deals on Kelowna to Chicago O'Hare Intl Airport flight tickets
Air Canada
28 Oct
YLW5:50 a.m.Kelowna
6h 47m
1 stop
ORD2:37 p.m.Chicago O'Hare Intl
7 Nov
ORD3:30 p.m.Chicago O'Hare Intl
8h 58m
1 stop
YLW11:28 p.m.Kelowna
C$ 474
Air Canada
28 Oct
YLW5:50 a.m.Kelowna
6h 47m
1 stop
ORD2:37 p.m.Chicago O'Hare Intl
7 Nov
ORD3:30 p.m.Chicago O'Hare Intl
8h 58m
1 stop
YLW11:28 p.m.Kelowna
C$ 542
Air Canada
28 Oct
YLW9:15 a.m.Kelowna
5h 55m
1 stop
ORD5:10 p.m.Chicago O'Hare Intl
7 Nov
ORD8:40 a.m.Chicago O'Hare Intl
11h 58m
2 stops
YLW7:38 p.m.Kelowna
C$ 557

momondo Fare Finder

 
Customize your flight search to find flights from Kelowna to Chicago O'Hare Intl Airport 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, momondo users made 96,600 searches. Data last updated 9 August 2026.
Use the filters below to find and compare flights from Kelowna to Chicago O'Hare Intl Airport 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

Fri 4/9

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

1 stop8h 35m

Chicago O'Hare Intl

Thu 10/9

5:30 p.m.-11:50 p.m.

1 stop8h 20m

C$ 417

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Wed 28/10

5:50 a.m.-2:37 p.m.

1 stop6h 47m

Chicago O'Hare Intl

Sat 7/11

3:30 p.m.-11:28 p.m.

1 stop8h 58m

C$ 474
Quickest round-trip

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Fri 4/9

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

1 stop6h 50m

Chicago O'Hare Intl

Fri 11/9

5:30 p.m.-11:50 p.m.

1 stop8h 20m

C$ 477

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Wed 28/10

5:50 a.m.-2:37 p.m.

1 stop6h 47m

Chicago O'Hare Intl

Sat 7/11

3:30 p.m.-11:28 p.m.

1 stop8h 58m

C$ 542

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Wed 28/10

9:15 a.m.-5:10 p.m.

1 stop5h 55m

Chicago O'Hare Intl

Sat 7/11

8:40 a.m.-7:38 p.m.

2 stops11h 58m

C$ 557

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Fri 4/9

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

1 stop8h 35m

Chicago O'Hare Intl

Fri 11/9

5:30 p.m.-7:00 a.m.

2 stops15h 30m

C$ 559

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Mon 5/10

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

1 stop8h 10m

Chicago O'Hare Intl

Wed 7/10

3:40 p.m.-11:12 p.m.

1 stop9h 32m

C$ 588

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Sat 19/9

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

1 stop8h 10m

Chicago O'Hare Intl

Sat 26/9

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

1 stop9h 47m

C$ 589

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Wed 30/9

8:30 p.m.-1:23 p.m.

2 stops14h 53m

Chicago O'Hare Intl

Sat 3/10

3:40 p.m.-11:12 p.m.

1 stop9h 32m

C$ 591

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Wed 30/9

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

1 stop8h 10m

Chicago O'Hare Intl

Sat 3/10

3:40 p.m.-11:12 p.m.

1 stop9h 32m

C$ 594

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Kelowna to Chicago O'Hare Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Kelowna to Chicago O'Hare Intl?

Air Canada is the most popular carrier operating from Kelowna to Chicago O'Hare Intl

When to book flights from Kelowna to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Kelowna to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Kelowna to Chicago O'Hare Intl Airport (YLW to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Kelowna to Chicago O'Hare Intl Airport

Fastest flight time

6h 47m

Direct flights

None
The fastest flight from Kelowna to Chicago O'Hare Intl Airport takes 6h 47m
There are no direct flights from Kelowna to Chicago O'Hare Intl Airport. There are no popular flight routes from Kelowna to Chicago O'Hare Intl Airport.
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Frequently asked questions about flying from Kelowna to Chicago O'Hare Intl Airport

  • How far is Kelowna to Chicago O'Hare Intl by plane?

    There are 2571.0 km between Kelowna and Chicago O'Hare Intl. By plane, this route typically takes 6h 47m.

  • When did momondo last update prices for flights from Kelowna Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Kelowna Airport to Chicago O'Hare Intl Airport refresh daily.

  • How old do you have to be to fly from Kelowna Airport to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Kelowna Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Schaumburg
Crystal Lake
Glenview
Waukegan
Rosemont
Des Plaines
Merrillville
Kenosha
Northbrook
Skokie
Tinley Park
Evanston
Downers Grove
Great Lakes
Hammond
Naperville
Harvey
Munster
Hoffman Estates
Elmhurst

Why use momondo?

Why should I use momondo to find a flight deal from Kelowna to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Kelowna to Chicago . Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Kelowna to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Kelowna which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Kelowna to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Kelowna.

I’m not ready to book a flight from Kelowna to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Kelowna. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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