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

Air Canada, United Airlines, and Porter 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 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$ 237 Cheap Flights from Kelowna to Chicago in 2026

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.

7:50 a.m. - 4:40 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

6h 50m1 stop Calgary

5:30 p.m. - 11:50 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

8h 20m1 stop Calgary

C$ 344WestJet

Fri, 2 Oct - Thu, 8 Oct

7:25 p.m. - 2:43 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

17h 18m1 stop Vancouver Intl

3:40 p.m. - 11:27 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

9h 47m1 stop Vancouver Intl

C$ 391Air Canada

Fri, 9 Oct - Fri, 16 Oct

10:50 p.m. - 9:00 a.m.YLW Kelowna-ORD Chicago O'Hare Intl

8h 10m1 stop Toronto Pearson Intl

2:15 p.m. - 9:52 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

9h 37m1 stop Toronto Pearson Intl

C$ 427Air Canada

Sat, 17 Oct - Wed, 21 Oct

8:30 p.m. - 1:23 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

14h 53m2 stops Vancouver Intl Toronto Pearson Intl

5:30 p.m. - 11:50 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

8h 20m1 stop Calgary

C$ 431Multiple Airlines

Fri, 2 Oct - Thu, 8 Oct

10:50 p.m. - 9:00 a.m.YLW Kelowna-ORD Chicago O'Hare Intl

8h 10m1 stop Toronto Pearson Intl

3:40 p.m. - 10:47 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

9h 07m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 436Air Canada

Tue, 15 Sep - Sat, 26 Sep

10:50 p.m. - 9:00 a.m.YLW Kelowna-ORD Chicago O'Hare Intl

8h 10m1 stop Toronto Pearson Intl

2:15 p.m. - 9:52 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

9h 37m1 stop Toronto Pearson Intl

C$ 440Air Canada

Sat, 17 Oct - Wed, 21 Oct

10:50 p.m. - 9:00 a.m.YLW Kelowna-ORD Chicago O'Hare Intl

8h 10m1 stop Toronto Pearson Intl

9:55 a.m. - 6:55 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

11h 00m2 stops Toronto Pearson Intl Calgary

C$ 442Air Canada

Tue, 15 Sep - Thu, 24 Sep

10:50 p.m. - 9:00 a.m.YLW Kelowna-ORD Chicago O'Hare Intl

8h 10m1 stop Toronto Pearson Intl

3:40 p.m. - 11:32 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

9h 52m1 stop Vancouver Intl

C$ 454Air Canada

Tue, 15 Sep - Thu, 24 Sep

10:50 p.m. - 1:23 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

12h 33m1 stop Toronto Pearson Intl

3:40 p.m. - 11:32 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

9h 52m1 stop Vancouver Intl

C$ 487Air Canada

Mon, 14 Sep - Wed, 23 Sep

10:20 a.m. - 10:05 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

9h 45m2 stops Vancouver Intl Salt Lake City

6:20 a.m. - 2:35 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

10h 15m2 stops Minneapolis St Paul Vancouver Intl

C$ 490Delta

Sat, 17 Oct - Wed, 21 Oct

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WestJet flights from Kelowna to Chicago

Our best WestJet deals on Kelowna to Chicago flight tickets

WestJet

2 Oct

YLW7:50 a.m.Kelowna

6h 50m

1 stop

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

8 Oct

ORD5:30 p.m.Chicago O'Hare Intl

8h 20m

1 stop

YLW11:50 p.m.Kelowna

C$ 344

WestJet

5 Sep

YLW7:50 a.m.Kelowna

6h 50m

1 stop

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

11 Sep

ORD5:30 p.m.Chicago O'Hare Intl

8h 20m

1 stop

YLW11:50 p.m.Kelowna

C$ 351

WestJet

15 Sep

YLW6:05 a.m.Kelowna

8h 35m

1 stop

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

20 Sep

ORD5:30 p.m.Chicago O'Hare Intl

6h 35m

1 stop

YLW10:05 p.m.Kelowna

C$ 510

Air Canada flights from Kelowna to Chicago

Our best Air Canada deals on Kelowna to Chicago flight tickets

Air Canada

9 Oct

YLW7:25 p.m.Kelowna

17h 18m

1 stop

ORD2:43 p.m.Chicago O'Hare Intl

16 Oct

ORD3:40 p.m.Chicago O'Hare Intl

9h 47m

1 stop

YLW11:27 p.m.Kelowna

C$ 391

Air Canada

17 Oct

YLW10:50 p.m.Kelowna

8h 10m

1 stop

ORD9:00 a.m.Chicago O'Hare Intl

21 Oct

ORD2:15 p.m.Chicago O'Hare Intl

9h 37m

1 stop

YLW9:52 p.m.Kelowna

C$ 427

Air Canada

15 Sep

YLW10:50 p.m.Kelowna

8h 10m

1 stop

ORD9:00 a.m.Chicago O'Hare Intl

26 Sep

ORD3:40 p.m.Chicago O'Hare Intl

9h 07m

1 stop

YLW10:47 p.m.Kelowna

C$ 436

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Fri 2/10

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

1 stop6h 50m

Chicago O'Hare Intl

Thu 8/10

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

1 stop8h 20m

C$ 344

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Fri 9/10

7:25 p.m.-2:43 p.m.

1 stop17h 18m

Chicago O'Hare Intl

Fri 16/10

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

1 stop9h 47m

C$ 391

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Sat 17/10

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

1 stop8h 10m

Chicago O'Hare Intl

Wed 21/10

2:15 p.m.-9:52 p.m.

1 stop9h 37m

C$ 427

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Fri 2/10

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

2 stops14h 53m

Chicago O'Hare Intl

Thu 8/10

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

1 stop8h 20m

C$ 431

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Tue 15/9

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

1 stop8h 10m

Chicago O'Hare Intl

Sat 26/9

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

1 stop9h 07m

C$ 436

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Sat 17/10

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

1 stop8h 10m

Chicago O'Hare Intl

Wed 21/10

2:15 p.m.-9:52 p.m.

1 stop9h 37m

C$ 440

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Tue 15/9

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

1 stop8h 10m

Chicago O'Hare Intl

Thu 24/9

9:55 a.m.-6:55 p.m.

2 stops11h 00m

C$ 442

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Tue 15/9

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

1 stop8h 10m

Chicago O'Hare Intl

Thu 24/9

3:40 p.m.-11:32 p.m.

1 stop9h 52m

C$ 454

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Mon 14/9

10:50 p.m.-1:23 p.m.

1 stop12h 33m

Chicago O'Hare Intl

Wed 23/9

3:40 p.m.-11:32 p.m.

1 stop9h 52m

C$ 487

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Sat 17/10

10:20 a.m.-10:05 p.m.

2 stops9h 45m

Chicago O'Hare Intl

Wed 21/10

6:20 a.m.-2:35 p.m.

2 stops10h 15m

C$ 490

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 January is another great option to travel to Chicago, with average flight prices from Kelowna averaging around C$ 0.

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$ 237
Fastest flight time	9h 45m
Direct flights	None

The best one-way flight to Chicago from Kelowna in the past 72 hours is C$ 237. The best round-trip flight deal from Kelowna to Chicago found on momondo in the last 72 hours is C$ 344.

The fastest flight from Kelowna to Chicago takes 9h 45m

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 9h 45m.
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 WestJet, making up 61% of the total bookings. Other popular airlines include Air Canada with 39%.

Merrillville

Benton Harbor

Hammond

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$ 237

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 9/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names, great deals

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WestJet flights from Kelowna to Chicago

Our best WestJet deals on Kelowna to Chicago flight tickets

Air Canada flights from Kelowna to Chicago

Our best Air Canada 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

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

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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