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Cheap flights from Kelowna to Chicago from C$ 239

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 21/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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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.
Air Canada Logo
9:25 a.m. - 8:15 p.m.
YLW
-
ORD
8h 50m
1 stop
Air Canada Logo
8:50 a.m. - 7:32 p.m.
ORD
-
YLW
12h 42m
1 stop
C$ 479Air Canada
Wed, 22 Apr - Wed, 29 Apr
Air Canada Logo
10:50 p.m. - 9:00 a.m.
YLW
-
ORD
8h 10m
1 stop
Air Canada Logo
8:35 p.m. - 12:18 p.m.
ORD
-
YLW
17h 43m
2 stops
C$ 484Air Canada
Fri, 1 May - Tue, 5 May
Delta Logo
6:05 a.m. - 6:52 p.m.
YLW
-
ORD
10h 47m
2 stops
Delta Logo
1:36 p.m. - 10:05 p.m.
ORD
-
YLW
10h 29m
2 stops
C$ 497Delta
Fri, 1 May - Tue, 5 May
United Airlines Logo
10:25 a.m. - 12:30 a.m.
YLW
-
ORD
12h 05m
2 stops
United Airlines Logo
8:50 a.m. - 10:53 p.m.
ORD
-
YLW
16h 03m
1 stop
C$ 499United Airlines
Wed, 22 Apr - Wed, 29 Apr
Multiple Airlines Logo
4:00 p.m. - 5:53 p.m.
YLW
-
ORD
23h 53m
2 stops
Multiple Airlines Logo
5:30 p.m. - 10:05 p.m.
ORD
-
YLW
6h 35m
1 stop
C$ 511Multiple Airlines
Fri, 24 Apr - Thu, 30 Apr
United Airlines Logo
9:25 a.m. - 12:30 a.m.
YLW
-
ORD
13h 05m
2 stops
United Airlines Logo
6:25 a.m. - 7:32 p.m.
ORD
-
YLW
15h 07m
2 stops
C$ 515United Airlines
Wed, 22 Apr - Wed, 29 Apr
Multiple Airlines Logo
12:00 p.m. - 12:10 p.m.
YLW
-
MDW
22h 10m
1 stop
Multiple Airlines Logo
6:15 a.m. - 11:50 p.m.
MDW
-
YLW
19h 35m
2 stops
C$ 605Multiple Airlines
Fri, 24 Apr - Fri, 1 May
Porter Airlines Logo
12:00 p.m. - 12:10 p.m.
YLW
-
MDW
22h 10m
1 stop
Porter Airlines Logo
3:20 p.m. - 10:47 a.m.
MDW
-
YLW
21h 27m
1 stop
C$ 700Porter Airlines
Fri, 24 Apr - Fri, 1 May
Porter Airlines Logo
12:00 p.m. - 10:15 a.m.
YLW
-
MDW
20h 15m
1 stop
Porter Airlines Logo
11:00 a.m. - 11:03 a.m.
MDW
-
YLW
26h 03m
1 stop
C$ 889Porter Airlines
Wed, 22 Apr - Wed, 29 Apr
Delta Logo
5:55 a.m. - 8:46 a.m.
YLW
-
MDW
24h 51m
2 stops
Delta Logo
1:24 p.m. - 10:05 p.m.
MDW
-
YLW
10h 41m
2 stops
C$ 1,010Delta
Sat, 2 May - Tue, 5 May

Delta flights from Kelowna to Chicago

Our best Delta deals on Kelowna to Chicago flight tickets
Delta
1 May
YLW6:05 a.m.Kelowna
10h 47m
2 stops
ORD6:52 p.m.Chicago O'Hare Intl
5 May
ORD1:36 p.m.Chicago O'Hare Intl
10h 29m
2 stops
YLW10:05 p.m.Kelowna
C$ 497
Delta
1 May
YLW6:05 a.m.Kelowna
10h 47m
2 stops
ORD6:52 p.m.Chicago O'Hare Intl
13 May
ORD3:47 p.m.Chicago O'Hare Intl
9h 43m
2 stops
YLW11:30 p.m.Kelowna
C$ 778
Delta
2 May
YLW5:55 a.m.Kelowna
24h 51m
2 stops
MDW8:46 a.m.Chicago Midway
5 May
MDW1:24 p.m.Chicago Midway
10h 41m
2 stops
YLW10:05 p.m.Kelowna
C$ 1,010

Air Canada flights from Kelowna to Chicago

Our best Air Canada deals on Kelowna to Chicago flight tickets
Air Canada
22 Apr
YLW9:25 a.m.Kelowna
8h 50m
1 stop
ORD8:15 p.m.Chicago O'Hare Intl
29 Apr
ORD8:50 a.m.Chicago O'Hare Intl
12h 42m
1 stop
YLW7:32 p.m.Kelowna
C$ 479
Air Canada
1 May
YLW10:50 p.m.Kelowna
8h 10m
1 stop
ORD9:00 a.m.Chicago O'Hare Intl
5 May
ORD8:35 p.m.Chicago O'Hare Intl
17h 43m
2 stops
YLW12:18 p.m.Kelowna
C$ 484
Air Canada
1 May
YLW10:50 p.m.Kelowna
8h 15m
1 stop
ORD9:05 a.m.Chicago O'Hare Intl
5 May
ORD9:55 a.m.Chicago O'Hare Intl
10h 58m
2 stops
YLW6:53 p.m.Kelowna
C$ 526

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 2 April 2026.
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

Cheapest round-trip

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 22/4

9:25 a.m.-8:15 p.m.

1 stop8h 50m

Chicago O'Hare Intl

Wed 29/4

8:50 a.m.-7:32 p.m.

1 stop12h 42m

C$ 479

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 1/5

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

1 stop8h 10m

Chicago O'Hare Intl

Tue 5/5

8:35 p.m.-12:18 p.m.

2 stops17h 43m

C$ 484
Quickest round-trip

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 1/5

6:05 a.m.-6:52 p.m.

2 stops10h 47m

Chicago O'Hare Intl

Tue 5/5

1:36 p.m.-10:05 p.m.

2 stops10h 29m

C$ 497

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 22/4

10:25 a.m.-12:30 a.m.

2 stops12h 05m

Chicago O'Hare Intl

Wed 29/4

8:50 a.m.-10:53 p.m.

1 stop16h 03m

C$ 499

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 24/4

4:00 p.m.-5:53 p.m.

2 stops23h 53m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-10:05 p.m.

1 stop6h 35m

C$ 511

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 22/4

9:25 a.m.-12:30 a.m.

2 stops13h 05m

Chicago O'Hare Intl

Wed 29/4

6:25 a.m.-7:32 p.m.

2 stops15h 07m

C$ 515

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 24/4

12:00 p.m.-12:10 p.m.

1 stop22h 10m

Chicago Midway

Fri 1/5

6:15 a.m.-11:50 p.m.

2 stops19h 35m

C$ 605

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 24/4

12:00 p.m.-12:10 p.m.

1 stop22h 10m

Chicago Midway

Fri 1/5

3:20 p.m.-10:47 a.m.

1 stop21h 27m

C$ 700

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 22/4

12:00 p.m.-10:15 a.m.

1 stop20h 15m

Chicago Midway

Wed 29/4

11:00 a.m.-11:03 a.m.

1 stop26h 03m

C$ 889

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sat 2/5

5:55 a.m.-8:46 a.m.

2 stops24h 51m

Chicago Midway

Tue 5/5

1:24 p.m.-10:05 p.m.

2 stops10h 41m

C$ 1,010

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

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

8h 15m

Direct flights

None
The fastest flight from Kelowna to Chicago takes 8h 15m
There are no direct flights from Kelowna to Chicago. There are no popular flight routes from Kelowna to Chicago.
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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 8h 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 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?

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
Munster

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