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.

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

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

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

Flights via Calgary (YYC) offer the lowest average round-trip price of C$ 364.

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.

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.

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 December 2025, 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$ 165 Cheap Flights from Kelowna to Chicago in 2025/26

Q: What is the typical price of a round-trip flight between Kelowna and Chicago?

Prices are currently typical for flights on this route. Typical prices usually range from C$ 295 to C$ 445. The lowest price recently found on this route was C$ 365.

1 adult

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Find the cheapest flights from Kelowna to Chicago

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One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

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$ 365Air Canada

Thu, 22 Jan - Mon, 26 Jan

7:55 p.m. - 1:35 p.m.

YLW

ORD

15h 40m1 stop

2:20 p.m. - 7:10 p.m.

ORD

YLW

6h 50m1 stop

C$ 375WestJet

Thu, 22 Jan - Mon, 26 Jan

11:20 p.m. - 5:48 p.m.

YLW

ORD

16h 28m1 stop

3:55 p.m. - 8:13 a.m.

ORD

YLW

18h 18m2 stops

C$ 416Air Canada

Thu, 22 Jan - Mon, 26 Jan

8:50 a.m. - 9:15 p.m.

YLW

ORD

10h 25m2 stops

8:45 a.m. - 12:50 p.m.

ORD

YLW

6h 05m1 stop

C$ 424United Airlines

Thu, 22 Jan - Mon, 26 Jan

8:50 a.m. - 9:15 p.m.

YLW

ORD

10h 25m2 stops

1:13 p.m. - 11:13 p.m.

ORD

YLW

12h 00m2 stops

C$ 433Air Canada

Thu, 22 Jan - Mon, 26 Jan

11:40 p.m. - 5:55 p.m.

YLW

MDW

16h 15m2 stops

1:49 p.m. - 11:55 p.m.

MDW

YLW

12h 06m2 stops

C$ 477Delta

Thu, 22 Jan - Mon, 26 Jan

12:35 p.m. - 11:53 p.m.

YLW

ORD

9h 18m2 stops

1:58 p.m. - 10:44 p.m.

ORD

YLW

10h 46m2 stops

C$ 543Delta

Thu, 22 Jan - Mon, 26 Jan

11:40 p.m. - 5:55 p.m.

YLW

MDW

16h 15m2 stops

1:26 p.m. - 10:44 p.m.

MDW

YLW

11h 18m2 stops

C$ 681Delta

Thu, 22 Jan - Mon, 26 Jan

Air Canada flights from Kelowna to Chicago

Our best Air Canada deals on Kelowna to Chicago flight tickets

Air Canada

22 Jan

YLW5:20 a.m.Kelowna

7h 21m

1 stop

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

26 Jan

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

9h 38m

1 stop

YLW11:13 p.m.Kelowna

C$ 365

Find similar

Air Canada

22 Jan

YLW11:20 p.m.Kelowna

18h 20m

1 stop

ORD7:40 p.m.Chicago O'Hare Intl

26 Jan

ORD3:55 p.m.Chicago O'Hare Intl

18h 18m

2 stops

YLW8:13 a.m.Kelowna

C$ 415

Find similar

Air Canada

22 Jan

YLW11:20 p.m.Kelowna

16h 28m

1 stop

ORD5:48 p.m.Chicago O'Hare Intl

26 Jan

ORD3:55 p.m.Chicago O'Hare Intl

18h 18m

2 stops

YLW8:13 a.m.Kelowna

C$ 416

Find similar

United Airlines flights from Kelowna to Chicago

Our best United Airlines deals on Kelowna to Chicago flight tickets

United Airlines

22 Jan

YLW8:50 a.m.Kelowna

10h 25m

2 stops

ORD9:15 p.m.Chicago O'Hare Intl

26 Jan

ORD8:45 a.m.Chicago O'Hare Intl

6h 05m

1 stop

YLW12:50 p.m.Kelowna

C$ 424

Find similar

United Airlines

23 Dec

YLW10:25 a.m.Kelowna

7h 29m

1 stop

ORD7:54 p.m.Chicago O'Hare Intl

2 Jan

ORD8:08 p.m.Chicago O'Hare Intl

19h 50m

2 stops

YLW1:58 p.m.Kelowna

C$ 982

Find similar

United Airlines

23 Dec

YLW1:25 p.m.Kelowna

15h 00m

2 stops

ORD6:25 a.m.Chicago O'Hare Intl

2 Jan

ORD9:40 p.m.Chicago O'Hare Intl

18h 18m

2 stops

YLW1:58 p.m.Kelowna

C$ 989

Find similar

Fly from

Fly to

Route

Depart

Return

Price

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 22/1

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

1 stop7h 21m

Chicago O'Hare Intl

Mon 26/1

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

1 stop9h 38m

C$ 365

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 22/1

7:55 p.m.-1:35 p.m.

1 stop15h 40m

Chicago O'Hare Intl

Mon 26/1

2:20 p.m.-7:10 p.m.

1 stop6h 50m

C$ 375

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 22/1

11:20 p.m.-5:48 p.m.

1 stop16h 28m

Chicago O'Hare Intl

Mon 26/1

3:55 p.m.-8:13 a.m.

2 stops18h 18m

C$ 416

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 22/1

8:50 a.m.-9:15 p.m.

2 stops10h 25m

Chicago O'Hare Intl

Mon 26/1

8:45 a.m.-12:50 p.m.

1 stop6h 05m

C$ 424

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 22/1

8:50 a.m.-9:15 p.m.

2 stops10h 25m

Chicago O'Hare Intl

Mon 26/1

1:13 p.m.-11:13 p.m.

2 stops12h 00m

C$ 433

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 22/1

11:40 p.m.-5:55 p.m.

2 stops16h 15m

Chicago Midway

Mon 26/1

1:49 p.m.-11:55 p.m.

2 stops12h 06m

C$ 477

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 22/1

12:35 p.m.-11:53 p.m.

2 stops9h 18m

Chicago O'Hare Intl

Mon 26/1

1:58 p.m.-10:44 p.m.

2 stops10h 46m

C$ 543

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 22/1

11:40 p.m.-5:55 p.m.

2 stops16h 15m

Chicago Midway

Mon 26/1

1:26 p.m.-10:44 p.m.

2 stops11h 18m

C$ 681

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sat 31/1

4:00 p.m.-3:58 p.m.

2 stops21h 58m

C$ 165

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sat 31/1

12:35 p.m.-3:58 p.m.

3 stops25h 23m

C$ 172

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

Prices

Airlines

Layovers

What is the typical price of a round-trip flight between Kelowna and Chicago?

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as C$ 500. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around C$ 620. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the evening is the cheapest time of day to fly from Kelowna to Chicago when you can find flight prices for as low as C$ 582. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 627 per ticket.

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	7h 29m
Direct flights	None

The fastest flight from Kelowna to Chicago takes 7h 29m

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 7h 29m.
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 December 2025, 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 Air Canada, making up 100% of the total bookings.

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$ 283	Free Cancellation	Rating 7.1 10,534 reviews		Search Air Canada flights

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.