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

Air Canada and United Airlines are the most popular carriers operating from Kelowna to Chicago

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 many operators does momondo search for flights from Kelowna Airport to Chicago?

As of November 2026, there is 1 operator available to choose from for flights from Kelowna Airport to Chicago.

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$ 284 Cheap Flights from Kelowna to Chicago in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Kelowna to Chicago

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

2:28 p.m. - 11:59 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

8h 31m1 stop Seattle/Tacoma Intl

3:19 p.m. - 10:37 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

8h 18m1 stop Seattle/Tacoma Intl

C$ 506Alaska Airlines

Tue, 1 Dec - Tue, 8 Dec

5:50 a.m. - 2:32 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

7h 42m1 stop Vancouver Intl

3:35 p.m. - 10:28 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

7h 53m1 stop Vancouver Intl

C$ 509Air Canada

Tue, 26 Jan - Wed, 27 Jan

5:50 a.m. - 2:32 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

7h 42m1 stop Vancouver Intl

3:35 p.m. - 10:28 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

7h 53m1 stop Vancouver Intl

C$ 509Air Canada

Tue, 12 Jan - Tue, 26 Jan

5:50 a.m. - 2:32 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

7h 42m1 stop Vancouver Intl

3:35 p.m. - 10:28 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

7h 53m1 stop Vancouver Intl

C$ 509Air Canada

Thu, 14 Jan - Thu, 28 Jan

5:50 a.m. - 2:32 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

7h 42m1 stop Vancouver Intl

3:35 p.m. - 10:28 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

7h 53m1 stop Vancouver Intl

C$ 510Air Canada

Tue, 26 Jan - Wed, 27 Jan

9:20 p.m. - 9:08 a.m.YLW Kelowna-ORD Chicago O'Hare Intl

10h 48m2 stops Vancouver Intl Toronto Pearson Intl

3:35 p.m. - 10:28 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

7h 53m1 stop Vancouver Intl

C$ 520Air Canada

Tue, 26 Jan - Wed, 27 Jan

9:20 p.m. - 9:08 a.m.YLW Kelowna-ORD Chicago O'Hare Intl

10h 48m2 stops Vancouver Intl Toronto Pearson Intl

3:35 p.m. - 10:28 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

7h 53m1 stop Vancouver Intl

C$ 521Air Canada

Tue, 26 Jan - Wed, 27 Jan

5:50 a.m. - 2:32 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

7h 42m1 stop Vancouver Intl

1:05 p.m. - 10:28 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

10h 23m2 stops Denver Intl Vancouver Intl

C$ 614United Airlines

Thu, 14 Jan - Thu, 28 Jan

5:50 a.m. - 2:32 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

7h 42m1 stop Vancouver Intl

10:42 a.m. - 10:28 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

12h 46m2 stops San Francisco Vancouver Intl

C$ 614United Airlines

Tue, 12 Jan - Tue, 26 Jan

10:15 a.m. - 9:32 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

10h 17m2 stops Calgary Denver Intl

7:00 a.m. - 10:28 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

16h 28m2 stops Los Angeles Vancouver Intl

C$ 622United Airlines

Tue, 12 Jan - Tue, 26 Jan

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Air Canada flights from Kelowna to Chicago

Our best Air Canada deals on Kelowna to Chicago flight tickets

Air Canada

26 Jan

YLW5:50 a.m.Kelowna

7h 42m

1 stop

ORD2:32 p.m.Chicago O'Hare Intl

27 Jan

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

7h 53m

1 stop

YLW10:28 p.m.Kelowna

C$ 509

Air Canada

26 Jan

YLW5:50 a.m.Kelowna

7h 42m

1 stop

ORD2:32 p.m.Chicago O'Hare Intl

27 Jan

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

7h 53m

1 stop

YLW10:28 p.m.Kelowna

C$ 510

Air Canada

26 Jan

YLW9:20 p.m.Kelowna

10h 48m

2 stops

ORD9:08 a.m.Chicago O'Hare Intl

27 Jan

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

7h 53m

1 stop

YLW10:28 p.m.Kelowna

C$ 520

WestJet flights from Kelowna to Chicago

Our best WestJet deals on Kelowna to Chicago flight tickets

WestJet

26 Nov

YLW5:20 a.m.Kelowna

10h 20m

2 stops

ORD4:40 p.m.Chicago O'Hare Intl

29 Nov

ORD5:46 p.m.Chicago O'Hare Intl

25h 09m

2 stops

YLW5:55 p.m.Kelowna

C$ 795

WestJet

26 Nov

YLW5:45 p.m.Kelowna

27h 02m

2 stops

ORD9:47 p.m.Chicago O'Hare Intl

29 Nov

ORD6:23 a.m.Chicago O'Hare Intl

14h 02m

2 stops

YLW7:25 p.m.Kelowna

C$ 822

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

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

Quickest round-trip

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

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 26/1

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

1 stop7h 53m

C$ 509

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Thu 14/1

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

1 stop7h 42m

Chicago O'Hare Intl

Thu 28/1

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

1 stop7h 53m

C$ 509

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$ 510

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Tue 26/1

9:20 p.m.-9:08 a.m.

2 stops10h 48m

Chicago O'Hare Intl

Wed 27/1

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

1 stop7h 53m

C$ 520

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Tue 26/1

9:20 p.m.-9:08 a.m.

2 stops10h 48m

Chicago O'Hare Intl

Wed 27/1

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

1 stop7h 53m

C$ 521

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Thu 14/1

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

1 stop7h 42m

Chicago O'Hare Intl

Thu 28/1

1:05 p.m.-10:28 p.m.

2 stops10h 23m

C$ 614

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 26/1

10:42 a.m.-10:28 p.m.

2 stops12h 46m

C$ 614

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Tue 12/1

10:15 a.m.-9:32 p.m.

2 stops10h 17m

Chicago O'Hare Intl

Tue 26/1

7:00 a.m.-10:28 p.m.

2 stops16h 28m

C$ 622

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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

Prices

Airlines

What is the cheapest month to fly to Chicago?

The month of May is another great option to travel to Chicago, with average flight prices from Kelowna averaging around C$ 442.

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

Best price found	C$ 284
Fastest flight time	5h 55m
Direct flights	None

The best one-way flight to Chicago from Kelowna in the past 72 hours is C$ 284. The best round-trip flight deal from Kelowna to Chicago found on momondo in the last 72 hours is C$ 506.

The fastest flight from Kelowna to Chicago takes 5h 55m

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

Search flight deals

Frequently asked questions about flying from Kelowna to Chicago

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 5h 55m.
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 many operators does momondo search for flights from Kelowna Airport to Chicago?
As of November 2026, there is 1 operator available to choose from for flights from Kelowna Airport to Chicago.
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 WestJet, making up 65% of the total bookings. Other popular airlines include Air Canada with 35%.

Best airlines flying from Kelowna to Chicago

Compare and see reviews for airlines that fly from Kelowna to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom C$ 530	Free Cancellation	Rating 7.1 11,847 reviews		Search Air Canada flights

Merrillville

Hammond

Benton Harbor

Munster

Valparaiso

Portage

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.

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Cheap flights from Kelowna to Chicago from C$ 284

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 10/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Air Canada flights from Kelowna to Chicago

Our best Air Canada deals on Kelowna to Chicago flight tickets

WestJet flights from Kelowna to Chicago

Our best WestJet deals on Kelowna to Chicago flight tickets

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How to get the cheapest flight ticket from Kelowna to Chicago

What is the cheapest month to fly to Chicago?

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

When to book flights from Kelowna to Chicago

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

Best price found

Fastest flight time

Direct flights

Frequently asked questions about flying from Kelowna to Chicago

Best airlines flying from Kelowna to Chicago

Compare and see reviews for airlines that fly from Kelowna to Chicago with momondo

Travelling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago

Fly your favourite airline to Chicago

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Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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