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Cheap flights from Kelowna to Chicago from C$ 209

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 27/2. 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
6:05 a.m. - 4:40 p.m.
YLW
-
ORD
8h 35m
1 stop
WestJet Logo
5:30 p.m. - 11:50 p.m.
ORD
-
YLW
8h 20m
1 stop
C$ 381WestJet
Wed, 17 Jun - Sat, 20 Jun
Air Canada Logo
5:20 a.m. - 2:41 p.m.
YLW
-
ORD
7h 21m
1 stop
Air Canada Logo
3:35 p.m. - 11:13 p.m.
ORD
-
YLW
9h 38m
1 stop
C$ 402Air Canada
Tue, 3 Mar - Tue, 17 Mar
Air Canada Logo
5:20 a.m. - 2:41 p.m.
YLW
-
ORD
7h 21m
1 stop
Air Canada Logo
3:35 p.m. - 11:13 p.m.
ORD
-
YLW
9h 38m
1 stop
C$ 405Air Canada
Tue, 3 Mar - Tue, 17 Mar
Air Canada Logo
5:20 a.m. - 2:41 p.m.
YLW
-
ORD
7h 21m
1 stop
Air Canada Logo
8:00 a.m. - 7:29 p.m.
ORD
-
YLW
13h 29m
2 stops
C$ 416Air Canada
Tue, 3 Mar - Tue, 17 Mar
Air Canada Logo
5:20 a.m. - 2:41 p.m.
YLW
-
ORD
7h 21m
1 stop
Air Canada Logo
10:00 a.m. - 7:29 p.m.
ORD
-
YLW
11h 29m
2 stops
C$ 417Air Canada
Tue, 3 Mar - Tue, 17 Mar
Air Canada Logo
5:20 a.m. - 2:41 p.m.
YLW
-
ORD
7h 21m
1 stop
Air Canada Logo
8:00 a.m. - 7:29 p.m.
ORD
-
YLW
13h 29m
2 stops
C$ 419Air Canada
Tue, 3 Mar - Tue, 17 Mar
Air Canada Logo
5:20 a.m. - 5:48 p.m.
YLW
-
ORD
10h 28m
2 stops
Air Canada Logo
8:00 a.m. - 7:29 p.m.
ORD
-
YLW
13h 29m
2 stops
C$ 434Air Canada
Tue, 3 Mar - Tue, 17 Mar
Air Canada Logo
5:20 a.m. - 7:45 p.m.
YLW
-
ORD
12h 25m
2 stops
Air Canada Logo
8:00 a.m. - 7:29 p.m.
ORD
-
YLW
13h 29m
2 stops
C$ 436Air Canada
Tue, 3 Mar - Tue, 17 Mar
WestJet Logo
7:50 a.m. - 4:40 p.m.
YLW
-
ORD
6h 50m
1 stop
WestJet Logo
5:30 p.m. - 7:00 a.m.
ORD
-
YLW
15h 30m
2 stops
C$ 478WestJet
Wed, 17 Jun - Sat, 20 Jun
Multiple Airlines Logo
7:00 a.m. - 10:45 p.m.
YLW
-
MDW
13h 45m
1 stop
Multiple Airlines Logo
6:00 a.m. - 9:48 p.m.
MDW
-
YLW
17h 48m
2 stops
C$ 583Multiple Airlines
Thu, 26 Mar - Thu, 2 Apr

Air Canada flights from Kelowna to Chicago

Our best Air Canada deals on Kelowna to Chicago flight tickets
Air Canada
3 Mar
YLW5:20 a.m.Kelowna
7h 21m
1 stop
ORD2:41 p.m.Chicago O'Hare Intl
17 Mar
ORD3:35 p.m.Chicago O'Hare Intl
9h 38m
1 stop
YLW11:13 p.m.Kelowna
C$ 402
Air Canada
3 Mar
YLW5:20 a.m.Kelowna
7h 21m
1 stop
ORD2:41 p.m.Chicago O'Hare Intl
17 Mar
ORD3:35 p.m.Chicago O'Hare Intl
9h 38m
1 stop
YLW11:13 p.m.Kelowna
C$ 405
Air Canada
3 Mar
YLW5:20 a.m.Kelowna
7h 21m
1 stop
ORD2:41 p.m.Chicago O'Hare Intl
17 Mar
ORD8:00 a.m.Chicago O'Hare Intl
13h 29m
2 stops
YLW7:29 p.m.Kelowna
C$ 416

United Airlines flights from Kelowna to Chicago

Our best United Airlines deals on Kelowna to Chicago flight tickets
United Airlines
28 Mar
YLW11:25 p.m.Kelowna
8h 25m
1 stop
ORD9:50 a.m.Chicago O'Hare Intl
4 Apr
ORD3:40 p.m.Chicago O'Hare Intl
9h 17m
1 stop
YLW10:57 p.m.Kelowna
C$ 501
United Airlines
26 Mar
YLW10:25 a.m.Kelowna
7h 35m
1 stop
ORD8:00 p.m.Chicago O'Hare Intl
2 Apr
ORD11:03 p.m.Chicago O'Hare Intl
20h 34m
2 stops
YLW5:37 p.m.Kelowna
C$ 508
United Airlines
26 Mar
YLW5:20 a.m.Kelowna
16h 32m
2 stops
ORD11:52 p.m.Chicago O'Hare Intl
2 Apr
ORD11:03 p.m.Chicago O'Hare Intl
22h 29m
2 stops
YLW7:32 p.m.Kelowna
C$ 516

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 12 February 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

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 17/6

6:05 a.m.-4:40 p.m.

1 stop8h 35m

Chicago O'Hare Intl

Sat 20/6

5:30 p.m.-11:50 p.m.

1 stop8h 20m

C$ 381

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 3/3

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

1 stop7h 21m

Chicago O'Hare Intl

Tue 17/3

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

1 stop9h 38m

C$ 402

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 3/3

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

1 stop7h 21m

Chicago O'Hare Intl

Tue 17/3

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

1 stop9h 38m

C$ 405

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 3/3

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

1 stop7h 21m

Chicago O'Hare Intl

Tue 17/3

8:00 a.m.-7:29 p.m.

2 stops13h 29m

C$ 416

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 3/3

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

1 stop7h 21m

Chicago O'Hare Intl

Tue 17/3

10:00 a.m.-7:29 p.m.

2 stops11h 29m

C$ 417

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 3/3

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

1 stop7h 21m

Chicago O'Hare Intl

Tue 17/3

8:00 a.m.-7:29 p.m.

2 stops13h 29m

C$ 419

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 3/3

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

2 stops10h 28m

Chicago O'Hare Intl

Tue 17/3

8:00 a.m.-7:29 p.m.

2 stops13h 29m

C$ 434

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 3/3

5:20 a.m.-7:45 p.m.

2 stops12h 25m

Chicago O'Hare Intl

Tue 17/3

8:00 a.m.-7:29 p.m.

2 stops13h 29m

C$ 436

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 17/6

7:50 a.m.-4:40 p.m.

1 stop6h 50m

Chicago O'Hare Intl

Sat 20/6

5:30 p.m.-7:00 a.m.

2 stops15h 30m

C$ 478

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 26/3

7:00 a.m.-10:45 p.m.

1 stop13h 45m

Chicago Midway

Thu 2/4

6:00 a.m.-9:48 p.m.

2 stops17h 48m

C$ 583

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 airline that flies from Kelowna to Chicago?

WestJet and Air Canada are the most popular carriers operating from Kelowna to 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

6h 50m

Direct flights

None
The fastest flight from Kelowna to Chicago takes 6h 50m
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 50m.

  • 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
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