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Cheap flights from Kelowna to Chicago from C$ 153

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 19/1. 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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Find the cheapest flights from Kelowna to Chicago

Cheap round-trip flights

United Airlines Logo
10:25 a.m. - 11:10 p.m.YLW-ORD
10h 45m2 stops
United Airlines Logo
7:00 a.m. - 10:58 p.m.ORD-YLW
17h 58m2 stops
C$ 373United Airlines
Find Deal
Tue, 16 Dec - Tue, 6 Jan
United Airlines Logo
10:25 a.m. - 5:00 a.m.YLW-ORD
16h 35m2 stops
United Airlines Logo
3:40 p.m. - 10:58 p.m.ORD-YLW
9h 18m1 stop
C$ 448United Airlines
Find Deal
Tue, 16 Dec - Sat, 3 Jan
Alaska Airlines Logo
5:35 p.m. - 11:59 p.m.YLW-ORD
28h 24m1 stop
Alaska Airlines Logo
7:45 a.m. - 12:34 p.m.ORD-YLW
6h 49m1 stop
C$ 484Alaska Airlines
Find Deal
Tue, 16 Dec - Wed, 7 Jan
United Airlines Logo
10:25 a.m. - 11:59 p.m.YLW-ORD
11h 34m2 stops
United Airlines Logo
7:10 a.m. - 10:58 p.m.ORD-YLW
17h 48m2 stops
C$ 508United Airlines
Find Deal
Tue, 16 Dec - Sat, 3 Jan
Air Canada Logo
8:55 p.m. - 2:41 p.m.YLW-ORD
15h 46m1 stop
Air Canada Logo
1:05 p.m. - 8:09 p.m.ORD-YLW
9h 04m1 stop
C$ 551Air Canada
Find Deal
Fri, 19 Dec - Mon, 5 Jan
Air Canada Logo
8:55 p.m. - 2:41 p.m.YLW-ORD
15h 46m1 stop
Air Canada Logo
3:40 p.m. - 10:58 p.m.ORD-YLW
9h 18m1 stop
C$ 583Air Canada
Find Deal
Sat, 20 Dec - Tue, 6 Jan
WestJet Logo
5:20 a.m. - 1:35 p.m.YLW-ORD
6h 15m1 stop
WestJet Logo
2:20 p.m. - 7:10 p.m.ORD-YLW
6h 50m1 stop
C$ 669WestJet
Find Deal
Fri, 19 Dec - Fri, 2 Jan
WestJet Logo
4:00 p.m. - 1:35 p.m.YLW-ORD
19h 35m1 stop
WestJet Logo
2:20 p.m. - 7:10 p.m.ORD-YLW
6h 50m1 stop
C$ 705WestJet
Find Deal
Sun, 21 Dec - Mon, 5 Jan
Delta Logo
7:55 p.m. - 11:57 a.m.YLW-MDW
14h 02m2 stops
Delta Logo
2:00 p.m. - 11:55 p.m.MDW-YLW
11h 55m2 stops
C$ 1,405Delta
Find Deal
Sat, 20 Dec - Tue, 6 Jan
Delta Logo
7:55 p.m. - 11:57 a.m.YLW-MDW
14h 02m2 stops
Delta Logo
2:00 p.m. - 11:55 p.m.MDW-YLW
11h 55m2 stops
C$ 1,514Delta
Find Deal
Sat, 20 Dec - Tue, 6 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$ 373
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
16 Dec
YLW10:25 a.m.Kelowna
11h 34m
2 stops
ORD11:59 p.m.Chicago O'Hare Intl
3 Jan
ORD7:10 a.m.Chicago O'Hare Intl
17h 48m
2 stops
YLW10:58 p.m.Kelowna
C$ 508
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$ 551
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$ 583
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$ 608
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Kelowna to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 16 September 2025.
Use the filters below to find and compare flights from Kelowna to Chicago that are best for you.

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$ 373

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

Tue 16/12

10:25 a.m.-11:59 p.m.

2 stops11h 34m

Chicago O'Hare Intl

Sat 3/1

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

2 stops17h 48m

C$ 508

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$ 551

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$ 583

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$ 669

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sun 21/12

4:00 p.m.-1:35 p.m.

1 stop19h 35m

Chicago O'Hare Intl

Mon 5/1

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

1 stop6h 50m

C$ 705

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$ 1,405

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$ 1,514

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

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$ 501. 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$ 622. 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$ 583. 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$ 629 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.
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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 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?

  • 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?

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 CanadaPriceFrom C$ 372Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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.

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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
Chicago Midway Airport
Chicago O'Hare Intl Airport