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Cheap flights from Kelowna to Chicago from C$ 224

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 6/12. 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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Find the cheapest flights from Kelowna to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
7:55 p.m. - 1:35 p.m.YLW-ORD
15h 40m1 stop
WestJet Logo
2:20 p.m. - 7:10 p.m.ORD-YLW
6h 50m1 stop
C$ 375WestJet
Find Deal
Thu, 4 Dec - Mon, 8 Dec
Alaska Airlines Logo
5:35 p.m. - 6:21 a.m.YLW-ORD
10h 46m1 stop
Alaska Airlines Logo
3:05 p.m. - 4:44 p.m.ORD-YLW
27h 39m2 stops
C$ 378Alaska Airlines
Find Deal
Thu, 4 Dec - Mon, 8 Dec
Air Canada Logo
5:20 a.m. - 2:41 p.m.YLW-ORD
7h 21m1 stop
Air Canada Logo
3:40 p.m. - 11:08 p.m.ORD-YLW
9h 28m1 stop
C$ 396Air Canada
Find Deal
Wed, 3 Dec - Mon, 8 Dec
Air Canada Logo
5:20 a.m. - 2:41 p.m.YLW-ORD
7h 21m1 stop
Air Canada Logo
3:40 p.m. - 11:08 p.m.ORD-YLW
9h 28m1 stop
C$ 413Air Canada
Find Deal
Wed, 3 Dec - Mon, 8 Dec
Multiple Airlines Logo
4:00 p.m. - 8:43 p.m.YLW-ORD
26h 43m2 stops
Multiple Airlines Logo
5:51 p.m. - 4:44 p.m.ORD-YLW
24h 53m1 stop
C$ 423Multiple Airlines
Find Deal
Wed, 3 Dec - Wed, 10 Dec
Multiple Airlines Logo
4:00 p.m. - 8:43 p.m.YLW-ORD
26h 43m2 stops
Multiple Airlines Logo
5:51 p.m. - 4:44 p.m.ORD-YLW
24h 53m1 stop
C$ 424Multiple Airlines
Find Deal
Wed, 3 Dec - Wed, 10 Dec
United Airlines Logo
5:20 a.m. - 9:08 p.m.YLW-ORD
13h 48m2 stops
United Airlines Logo
12:45 p.m. - 11:08 p.m.ORD-YLW
12h 23m2 stops
C$ 494United Airlines
Find Deal
Wed, 3 Dec - Wed, 10 Dec
United Airlines Logo
10:25 a.m. - 9:40 a.m.YLW-ORD
21h 15m3 stops
United Airlines Logo
9:10 a.m. - 8:09 p.m.ORD-YLW
12h 59m2 stops
C$ 613United Airlines
Find Deal
Wed, 3 Dec - Mon, 8 Dec
Delta Logo
7:35 p.m. - 11:55 a.m.YLW-MDW
14h 20m2 stops
Delta Logo
1:50 p.m. - 11:55 p.m.MDW-YLW
12h 05m2 stops
C$ 696Delta
Find Deal
Wed, 3 Dec - Wed, 10 Dec
Delta Logo
7:35 p.m. - 11:55 a.m.YLW-MDW
14h 20m2 stops
Delta Logo
1:50 p.m. - 11:55 p.m.MDW-YLW
12h 05m2 stops
C$ 909Delta
Find Deal
Wed, 3 Dec - Mon, 8 Dec

Air Canada flights from Kelowna to Chicago

Our best Air Canada deals on Kelowna to Chicago flight tickets
Air Canada
3 Dec
YLW5:20 a.m.Kelowna
7h 21m
1 stop
ORD2:41 p.m.Chicago O'Hare Intl
8 Dec
ORD3:40 p.m.Chicago O'Hare Intl
9h 28m
1 stop
YLW11:08 p.m.Kelowna
C$ 396
Find similar
Air Canada
3 Dec
YLW5:20 a.m.Kelowna
7h 21m
1 stop
ORD2:41 p.m.Chicago O'Hare Intl
8 Dec
ORD3:40 p.m.Chicago O'Hare Intl
9h 28m
1 stop
YLW11:08 p.m.Kelowna
C$ 413
Find similar
Air Canada
3 Dec
YLW5:20 a.m.Kelowna
9h 41m
2 stops
ORD5:01 p.m.Chicago O'Hare Intl
10 Dec
ORD10:45 a.m.Chicago O'Hare Intl
14h 23m
2 stops
YLW11:08 p.m.Kelowna
C$ 496
Find similar

United Airlines flights from Kelowna to Chicago

Our best United Airlines deals on Kelowna to Chicago flight tickets
United Airlines
3 Dec
YLW5:20 a.m.Kelowna
13h 48m
2 stops
ORD9:08 p.m.Chicago O'Hare Intl
10 Dec
ORD12:45 p.m.Chicago O'Hare Intl
12h 23m
2 stops
YLW11:08 p.m.Kelowna
C$ 494
Find similar
United Airlines
3 Dec
YLW10:25 a.m.Kelowna
21h 15m
3 stops
ORD9:40 a.m.Chicago O'Hare Intl
8 Dec
ORD9:10 a.m.Chicago O'Hare Intl
12h 59m
2 stops
YLW8:09 p.m.Kelowna
C$ 613
Find similar
United Airlines
20 Dec
YLW5:20 a.m.Kelowna
16h 39m
2 stops
ORD11:59 p.m.Chicago O'Hare Intl
6 Jan
ORD6:47 a.m.Chicago O'Hare Intl
18h 21m
2 stops
YLW11:08 p.m.Kelowna
C$ 806
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 23 October 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

Thu 4/12

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

1 stop15h 40m

Chicago O'Hare Intl

Mon 8/12

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

1 stop6h 50m

C$ 375

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 4/12

5:35 p.m.-6:21 a.m.

1 stop10h 46m

Chicago O'Hare Intl

Mon 8/12

3:05 p.m.-4:44 p.m.

2 stops27h 39m

C$ 378

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 3/12

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

1 stop7h 21m

Chicago O'Hare Intl

Mon 8/12

3:40 p.m.-11:08 p.m.

1 stop9h 28m

C$ 396

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 3/12

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

1 stop7h 21m

Chicago O'Hare Intl

Mon 8/12

3:40 p.m.-11:08 p.m.

1 stop9h 28m

C$ 413

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 3/12

4:00 p.m.-8:43 p.m.

2 stops26h 43m

Chicago O'Hare Intl

Wed 10/12

5:51 p.m.-4:44 p.m.

1 stop24h 53m

C$ 423

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 3/12

4:00 p.m.-8:43 p.m.

2 stops26h 43m

Chicago O'Hare Intl

Wed 10/12

5:51 p.m.-4:44 p.m.

1 stop24h 53m

C$ 424

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 3/12

5:20 a.m.-9:08 p.m.

2 stops13h 48m

Chicago O'Hare Intl

Wed 10/12

12:45 p.m.-11:08 p.m.

2 stops12h 23m

C$ 494

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 3/12

10:25 a.m.-9:40 a.m.

3 stops21h 15m

Chicago O'Hare Intl

Mon 8/12

9:10 a.m.-8:09 p.m.

2 stops12h 59m

C$ 613

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 3/12

7:35 p.m.-11:55 a.m.

2 stops14h 20m

Chicago Midway

Wed 10/12

1:50 p.m.-11:55 p.m.

2 stops12h 05m

C$ 696

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 3/12

7:35 p.m.-11:55 a.m.

2 stops14h 20m

Chicago Midway

Mon 8/12

1:50 p.m.-11:55 p.m.

2 stops12h 05m

C$ 909

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 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$ 442.

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$ 508. 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$ 630. 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$ 591. 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$ 638 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 7h 21m.

  • 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$ 288Free CancellationRating
7.1
10,350 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