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

WestJet, 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 September 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$ 134 Cheap Flights from Kelowna to Chicago in 2025/26

1 adult

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Find the cheapest flights from Kelowna to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

10:25 a.m. - 11:10 p.m.YLW-ORD

10h 45m2 stops

7:00 a.m. - 10:58 p.m.ORD-YLW

17h 58m2 stops

C$ 374United Airlines

Find Deal

Tue, 16 Dec - Tue, 6 Jan

10:25 a.m. - 5:00 a.m.YLW-ORD

16h 35m2 stops

3:40 p.m. - 10:58 p.m.ORD-YLW

9h 18m1 stop

C$ 448United Airlines

Find Deal

Tue, 16 Dec - Sat, 3 Jan

5:35 p.m. - 11:59 p.m.YLW-ORD

28h 24m1 stop

7:45 a.m. - 12:34 p.m.ORD-YLW

6h 49m1 stop

C$ 484Alaska Airlines

Find Deal

Tue, 16 Dec - Wed, 7 Jan

12:00 p.m. - 8:05 a.m.YLW-ORD

18h 05m1 stop

12:53 p.m. - 10:58 p.m.ORD-YLW

12h 05m2 stops

C$ 502United Airlines

Find Deal

Sat, 20 Dec - Tue, 6 Jan

8:55 p.m. - 2:41 p.m.YLW-ORD

15h 46m1 stop

1:05 p.m. - 8:09 p.m.ORD-YLW

9h 04m1 stop

C$ 552Air Canada

Find Deal

Fri, 19 Dec - Mon, 5 Jan

8:55 p.m. - 2:41 p.m.YLW-ORD

15h 46m1 stop

3:40 p.m. - 10:58 p.m.ORD-YLW

9h 18m1 stop

C$ 584Air Canada

Find Deal

Sat, 20 Dec - Tue, 6 Jan

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

6h 15m1 stop

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

6h 50m1 stop

C$ 670WestJet

Find Deal

Fri, 19 Dec - Fri, 2 Jan

3:00 p.m. - 1:35 p.m.YLW-ORD

20h 35m1 stop

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

6h 50m1 stop

C$ 706WestJet

Find Deal

Sun, 21 Dec - Fri, 2 Jan

7:55 p.m. - 11:57 a.m.YLW-MDW

14h 02m2 stops

2:00 p.m. - 11:55 p.m.MDW-YLW

11h 55m2 stops

C$ 1,408Delta

Find Deal

Sat, 20 Dec - Tue, 6 Jan

9:05 a.m. - 11:32 p.m.YLW-MDW

12h 27m2 stops

2:00 p.m. - 11:55 p.m.MDW-YLW

11h 55m2 stops

C$ 2,116Delta

Find Deal

Fri, 19 Dec - Mon, 5 Jan

United Airlines flights from Kelowna to Chicago

Our best United Airlines deals on Kelowna to Chicago flight tickets

United Airlines

16 Dec

YLW10:25 a.m.Kelowna

10h 45m

2 stops

ORD11:10 p.m.Chicago O'Hare Intl

6 Jan

ORD7:00 a.m.Chicago O'Hare Intl

17h 58m

2 stops

YLW10:58 p.m.Kelowna

C$ 374

Find similar

United Airlines

16 Dec

YLW10:25 a.m.Kelowna

16h 35m

2 stops

ORD5:00 a.m.Chicago O'Hare Intl

3 Jan

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

9h 18m

1 stop

YLW10:58 p.m.Kelowna

C$ 448

Find similar

United Airlines

20 Dec

YLW12:00 p.m.Kelowna

18h 05m

1 stop

ORD8:05 a.m.Chicago O'Hare Intl

6 Jan

ORD12:53 p.m.Chicago O'Hare Intl

12h 05m

2 stops

YLW10:58 p.m.Kelowna

C$ 502

Find similar

Air Canada flights from Kelowna to Chicago

Our best Air Canada deals on Kelowna to Chicago flight tickets

Air Canada

19 Dec

YLW8:55 p.m.Kelowna

15h 46m

1 stop

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

5 Jan

ORD1:05 p.m.Chicago O'Hare Intl

9h 04m

1 stop

YLW8:09 p.m.Kelowna

C$ 552

Find similar

Air Canada

20 Dec

YLW8:55 p.m.Kelowna

15h 46m

1 stop

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

6 Jan

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

9h 18m

1 stop

YLW10:58 p.m.Kelowna

C$ 584

Find similar

Air Canada

20 Dec

YLW10:25 a.m.Kelowna

11h 34m

2 stops

ORD11:59 p.m.Chicago O'Hare Intl

6 Jan

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

6h 05m

1 stop

YLW12:50 p.m.Kelowna

C$ 609

Find similar

Fly from

Fly to

Route

Depart

Return

Price

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 16/12

10:25 a.m.-11:10 p.m.

2 stops10h 45m

Chicago O'Hare Intl

Tue 6/1

7:00 a.m.-10:58 p.m.

2 stops17h 58m

C$ 374

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 16/12

10:25 a.m.-5:00 a.m.

2 stops16h 35m

Chicago O'Hare Intl

Sat 3/1

3:40 p.m.-10:58 p.m.

1 stop9h 18m

C$ 448

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 16/12

5:35 p.m.-11:59 p.m.

1 stop28h 24m

Chicago O'Hare Intl

Wed 7/1

7:45 a.m.-12:34 p.m.

1 stop6h 49m

C$ 484

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sat 20/12

12:00 p.m.-8:05 a.m.

1 stop18h 05m

Chicago O'Hare Intl

Tue 6/1

12:53 p.m.-10:58 p.m.

2 stops12h 05m

C$ 502

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 19/12

8:55 p.m.-2:41 p.m.

1 stop15h 46m

Chicago O'Hare Intl

Mon 5/1

1:05 p.m.-8:09 p.m.

1 stop9h 04m

C$ 552

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sat 20/12

8:55 p.m.-2:41 p.m.

1 stop15h 46m

Chicago O'Hare Intl

Tue 6/1

3:40 p.m.-10:58 p.m.

1 stop9h 18m

C$ 584

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 19/12

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

1 stop6h 15m

Chicago O'Hare Intl

Fri 2/1

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

1 stop6h 50m

C$ 670

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sun 21/12

3:00 p.m.-1:35 p.m.

1 stop20h 35m

Chicago O'Hare Intl

Fri 2/1

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

1 stop6h 50m

C$ 706

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sat 20/12

7:55 p.m.-11:57 a.m.

2 stops14h 02m

Chicago Midway

Tue 6/1

2:00 p.m.-11:55 p.m.

2 stops11h 55m

C$ 1,408

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 19/12

9:05 a.m.-11:32 p.m.

2 stops12h 27m

Chicago Midway

Mon 5/1

2:00 p.m.-11:55 p.m.

2 stops11h 55m

C$ 2,116

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 August is another great option to travel to Chicago, with average flight prices from Kelowna averaging around C$ 437.

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$ 502. 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$ 623. 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$ 584. 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$ 630 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

Direct flights	None

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

Search flight deals

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 6h 15m.
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 September 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$ 372	Free Cancellation	Rating 7.1 10,000 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.