Which airport is the most popular layover for flights between Kelowna and Chicago?

Calgary (YYC) was the most common stop: 50% of momondo users choosing one-stop flights on this route connected there.

Which layover airport offers the lowest fares from Kelowna to Chicago?

Flights via Calgary (YYC) offer the lowest average round-trip price of C$ 362.

Which layover airport has the shortest travel time from Kelowna to Chicago?

Flights connecting via Calgary (YYC) have the shortest average one-way travel time: 7h 43m.

Which layover airport has the shortest connection time from Kelowna to Chicago?

Calgary (YYC) has the shortest average layover time for this route: 2h 16m.

When did momondo last update prices for flights from Kelowna Airport to Chicago?

Prices for flights from Kelowna Airport to Chicago are refreshed on a daily basis.

How old do you have to be to fly from Kelowna Airport to Chicago?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Kelowna Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

C$ 235 Cheap Flights from Kelowna to Chicago in 2026

1 adult

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Find the cheapest flights from Kelowna to Chicago

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7:00 a.m. - 11:41 p.m.

YLW

MDW

14h 41m1 stop

3:21 p.m. - 7:00 p.m.

MDW

YLW

29h 39m2 stops

C$ 265Multiple Airlines

Thu, 26 Feb - Sun, 1 Mar

5:20 a.m. - 1:35 p.m.

YLW

ORD

6h 15m1 stop

2:20 p.m. - 7:08 p.m.

ORD

YLW

6h 48m1 stop

C$ 283WestJet

Fri, 13 Feb - Fri, 20 Feb

5:20 a.m. - 1:35 p.m.

YLW

ORD

6h 15m1 stop

2:20 p.m. - 11:12 p.m.

ORD

YLW

10h 52m2 stops

C$ 292WestJet

Fri, 13 Feb - Fri, 20 Feb

7:00 a.m. - 11:41 p.m.

YLW

MDW

14h 41m1 stop

3:21 p.m. - 9:35 a.m.

MDW

YLW

20h 14m2 stops

C$ 310Multiple Airlines

Thu, 26 Feb - Sun, 1 Mar

9:05 a.m. - 11:56 p.m.

YLW

ORD

12h 51m1 stop

9:15 a.m. - 7:00 p.m.

ORD

YLW

11h 45m2 stops

C$ 366Multiple Airlines

Sat, 28 Feb - Tue, 3 Mar

5:20 a.m. - 1:35 p.m.

YLW

ORD

6h 15m1 stop

2:20 p.m. - 7:08 p.m.

ORD

YLW

6h 48m1 stop

C$ 387WestJet

Mon, 2 Feb - Fri, 6 Feb

5:20 a.m. - 2:41 p.m.

YLW

ORD

7h 21m1 stop

2:00 p.m. - 10:20 p.m.

ORD

YLW

10h 20m1 stop

C$ 397Air Canada

Thu, 26 Feb - Sun, 1 Mar

5:20 a.m. - 2:41 p.m.

YLW

ORD

7h 21m1 stop

3:35 p.m. - 11:13 p.m.

ORD

YLW

9h 38m1 stop

C$ 409Air Canada

Mon, 2 Feb - Fri, 6 Feb

11:25 p.m. - 2:55 p.m.

YLW

ORD

13h 30m2 stops

3:35 p.m. - 11:13 p.m.

ORD

YLW

9h 38m1 stop

C$ 423Air Canada

Mon, 2 Feb - Fri, 6 Feb

8:35 p.m. - 5:48 p.m.

YLW

ORD

19h 13m2 stops

3:35 p.m. - 11:13 p.m.

ORD

YLW

9h 38m1 stop

C$ 450Air Canada

Mon, 2 Feb - Fri, 6 Feb

WestJet flights from Kelowna to Chicago

Our best WestJet deals on Kelowna to Chicago flight tickets

WestJet

2 Feb

YLW5:20 a.m.Kelowna

6h 15m

1 stop

ORD1:35 p.m.Chicago O'Hare Intl

6 Feb

ORD2:20 p.m.Chicago O'Hare Intl

6h 48m

1 stop

YLW7:08 p.m.Kelowna

C$ 387

Find similar

WestJet

2 Feb

YLW5:20 a.m.Kelowna

6h 15m

1 stop

ORD1:35 p.m.Chicago O'Hare Intl

6 Feb

ORD2:20 p.m.Chicago O'Hare Intl

6h 48m

1 stop

YLW7:08 p.m.Kelowna

C$ 425

Find similar

WestJet

2 Feb

YLW5:20 a.m.Kelowna

6h 15m

1 stop

ORD1:35 p.m.Chicago O'Hare Intl

5 Feb

ORD11:15 a.m.Chicago O'Hare Intl

37h 26m

2 stops

YLW10:41 p.m.Kelowna

C$ 633

Find similar

Air Canada flights from Kelowna to Chicago

Our best Air Canada deals on Kelowna to Chicago flight tickets

Air Canada

26 Feb

YLW5:20 a.m.Kelowna

7h 21m

1 stop

ORD2:41 p.m.Chicago O'Hare Intl

1 Mar

ORD2:00 p.m.Chicago O'Hare Intl

10h 20m

1 stop

YLW10:20 p.m.Kelowna

C$ 397

Find similar

Air Canada

2 Feb

YLW5:20 a.m.Kelowna

7h 21m

1 stop

ORD2:41 p.m.Chicago O'Hare Intl

6 Feb

ORD3:35 p.m.Chicago O'Hare Intl

9h 38m

1 stop

YLW11:13 p.m.Kelowna

C$ 409

Find similar

Air Canada

2 Feb

YLW11:25 p.m.Kelowna

13h 30m

2 stops

ORD2:55 p.m.Chicago O'Hare Intl

6 Feb

ORD3:35 p.m.Chicago O'Hare Intl

9h 38m

1 stop

YLW11:13 p.m.Kelowna

C$ 423

Find similar

Fly from

Fly to

Route

Depart

Return

Price

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 26/2

7:00 a.m.-11:41 p.m.

1 stop14h 41m

Chicago Midway

Sun 1/3

3:21 p.m.-7:00 p.m.

2 stops29h 39m

C$ 265

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 13/2

5:20 a.m.-1:35 p.m.

1 stop6h 15m

Chicago O'Hare Intl

Fri 20/2

2:20 p.m.-7:08 p.m.

1 stop6h 48m

C$ 283

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 13/2

5:20 a.m.-1:35 p.m.

1 stop6h 15m

Chicago O'Hare Intl

Fri 20/2

2:20 p.m.-11:12 p.m.

2 stops10h 52m

C$ 292

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 26/2

7:00 a.m.-11:41 p.m.

1 stop14h 41m

Chicago Midway

Sun 1/3

3:21 p.m.-9:35 a.m.

2 stops20h 14m

C$ 310

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sat 28/2

9:05 a.m.-11:56 p.m.

1 stop12h 51m

Chicago O'Hare Intl

Tue 3/3

9:15 a.m.-7:00 p.m.

2 stops11h 45m

C$ 366

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 2/2

5:20 a.m.-1:35 p.m.

1 stop6h 15m

Chicago O'Hare Intl

Fri 6/2

2:20 p.m.-7:08 p.m.

1 stop6h 48m

C$ 387

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 26/2

5:20 a.m.-2:41 p.m.

1 stop7h 21m

Chicago O'Hare Intl

Sun 1/3

2:00 p.m.-10:20 p.m.

1 stop10h 20m

C$ 397

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 2/2

5:20 a.m.-2:41 p.m.

1 stop7h 21m

Chicago O'Hare Intl

Fri 6/2

3:35 p.m.-11:13 p.m.

1 stop9h 38m

C$ 409

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 2/2

11:25 p.m.-2:55 p.m.

2 stops13h 30m

Chicago O'Hare Intl

Fri 6/2

3:35 p.m.-11:13 p.m.

1 stop9h 38m

C$ 423

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 2/2

8:35 p.m.-5:48 p.m.

2 stops19h 13m

Chicago O'Hare Intl

Fri 6/2

3:35 p.m.-11:13 p.m.

1 stop9h 38m

C$ 450

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first

How to get the cheapest flight ticket from Kelowna to Chicago

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

Airlines

Layovers

What is the cheapest airline that flies from Kelowna to Chicago?

WestJet and Delta are the most popular carriers operating from Kelowna to Chicago

When to book flights from Kelowna to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Kelowna to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Kelowna to Chicago (YLW to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Kelowna to Chicago

Fastest flight time	10h 36m
Direct flights	None

The fastest flight from Kelowna to Chicago takes 10h 36m

There are no direct flights from Kelowna to Chicago. There are no popular flight routes from Kelowna to Chicago.

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How far is Kelowna to Chicago by plane?
The straight-line distance from Kelowna to Chicago is 2596.6 km. By plane, this route typically takes 10h 36m.
When did momondo last update prices for flights from Kelowna Airport to Chicago?
Prices for flights from Kelowna Airport to Chicago are refreshed on a daily basis.
How old do you have to be to fly from Kelowna Airport to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Kelowna Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular airline from Kelowna to Chicago?
Based on momondo bookings for flights between Kelowna and Chicago, the leading airline is Air Canada, making up 100% of the total bookings.

Munster

Hammond

Merrillville

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Kelowna to Chicago for you.

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

Flights from Kelowna to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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.