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Cheap flights from Kelowna to Chicago from C$ 282

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 23/6. 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.
WestJet Logo
7:50 a.m. - 4:40 p.m.
YLW
-
ORD
6h 50m
1 stop
WestJet Logo
5:30 p.m. - 10:05 p.m.
ORD
-
YLW
6h 35m
1 stop
C$ 492WestJet
Fri, 16 Oct - Mon, 19 Oct
Air Canada Logo
11:30 p.m. - 9:00 a.m.
YLW
-
ORD
7h 30m
1 stop
Air Canada Logo
3:40 p.m. - 11:12 p.m.
ORD
-
YLW
9h 32m
1 stop
C$ 499Air Canada
Fri, 11 Sep - Tue, 15 Sep
Air Canada Logo
8:30 p.m. - 1:23 p.m.
YLW
-
ORD
14h 53m
2 stops
Air Canada Logo
3:40 p.m. - 11:12 p.m.
ORD
-
YLW
9h 32m
1 stop
C$ 500Air Canada
Fri, 11 Sep - Tue, 15 Sep
WestJet Logo
6:05 a.m. - 4:40 p.m.
YLW
-
ORD
8h 35m
1 stop
WestJet Logo
5:30 p.m. - 10:05 p.m.
ORD
-
YLW
6h 35m
1 stop
C$ 543WestJet
Fri, 11 Sep - Tue, 15 Sep
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$ 544WestJet
Fri, 11 Sep - Tue, 15 Sep
United Airlines Logo
5:25 a.m. - 9:30 p.m.
YLW
-
ORD
14h 05m
2 stops
United Airlines Logo
3:40 p.m. - 11:12 p.m.
ORD
-
YLW
9h 32m
1 stop
C$ 580United Airlines
Fri, 11 Sep - Tue, 15 Sep
Delta Logo
6:05 a.m. - 4:40 p.m.
YLW
-
ORD
8h 35m
1 stop
Delta Logo
11:30 a.m. - 10:05 p.m.
ORD
-
YLW
12h 35m
2 stops
C$ 632Delta
Fri, 11 Sep - Tue, 15 Sep
Delta Logo
6:05 a.m. - 6:37 p.m.
YLW
-
MDW
10h 32m
2 stops
Delta Logo
12:30 p.m. - 11:30 p.m.
MDW
-
YLW
13h 00m
2 stops
C$ 639Delta
Tue, 20 Oct - Sat, 24 Oct
Multiple Airlines Logo
12:50 p.m. - 9:35 a.m.
YLW
-
MDW
18h 45m
2 stops
Multiple Airlines Logo
10:15 a.m. - 7:00 a.m.
MDW
-
YLW
22h 45m
3 stops
C$ 942Multiple Airlines
Thu, 11 Jun - Mon, 15 Jun
Multiple Airlines Logo
12:50 p.m. - 9:40 a.m.
YLW
-
MDW
18h 50m
2 stops
Multiple Airlines Logo
9:59 a.m. - 11:55 a.m.
MDW
-
YLW
27h 56m
3 stops
C$ 947Multiple Airlines
Fri, 24 Jul - Sat, 8 Aug

Air Canada flights from Kelowna to Chicago

Our best Air Canada deals on Kelowna to Chicago flight tickets
Air Canada
11 Sep
YLW11:30 p.m.Kelowna
7h 30m
1 stop
ORD9:00 a.m.Chicago O'Hare Intl
15 Sep
ORD3:40 p.m.Chicago O'Hare Intl
9h 32m
1 stop
YLW11:12 p.m.Kelowna
C$ 499
Air Canada
11 Sep
YLW8:30 p.m.Kelowna
14h 53m
2 stops
ORD1:23 p.m.Chicago O'Hare Intl
15 Sep
ORD3:40 p.m.Chicago O'Hare Intl
9h 32m
1 stop
YLW11:12 p.m.Kelowna
C$ 500
Air Canada
11 Sep
YLW8:30 p.m.Kelowna
14h 53m
2 stops
ORD1:23 p.m.Chicago O'Hare Intl
15 Sep
ORD5:00 a.m.Chicago O'Hare Intl
11h 12m
2 stops
YLW2:12 p.m.Kelowna
C$ 584

United Airlines flights from Kelowna to Chicago

Our best United Airlines deals on Kelowna to Chicago flight tickets
United Airlines
11 Sep
YLW5:25 a.m.Kelowna
14h 05m
2 stops
ORD9:30 p.m.Chicago O'Hare Intl
15 Sep
ORD3:40 p.m.Chicago O'Hare Intl
9h 32m
1 stop
YLW11:12 p.m.Kelowna
C$ 580
United Airlines
1 Jul
YLW7:25 p.m.Kelowna
8h 15m
1 stop
ORD5:40 a.m.Chicago O'Hare Intl
3 Jul
ORD9:50 p.m.Chicago O'Hare Intl
18h 24m
2 stops
YLW2:14 p.m.Kelowna
C$ 678
United Airlines
28 Jul
YLW11:00 p.m.Kelowna
8h 45m
1 stop
ORD9:45 a.m.Chicago O'Hare Intl
26 Aug
ORD5:00 a.m.Chicago O'Hare Intl
9h 19m
2 stops
YLW12:19 p.m.Kelowna
C$ 692

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 18 May 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
Quickest round-trip

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 16/10

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

1 stop6h 50m

Chicago O'Hare Intl

Mon 19/10

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

1 stop6h 35m

C$ 492

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 11/9

11:30 p.m.-9:00 a.m.

1 stop7h 30m

Chicago O'Hare Intl

Tue 15/9

3:40 p.m.-11:12 p.m.

1 stop9h 32m

C$ 499

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 11/9

8:30 p.m.-1:23 p.m.

2 stops14h 53m

Chicago O'Hare Intl

Tue 15/9

3:40 p.m.-11:12 p.m.

1 stop9h 32m

C$ 500

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 11/9

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

1 stop8h 35m

Chicago O'Hare Intl

Tue 15/9

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

1 stop6h 35m

C$ 543

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 11/9

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

1 stop8h 35m

Chicago O'Hare Intl

Tue 15/9

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

1 stop8h 20m

C$ 544

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 11/9

5:25 a.m.-9:30 p.m.

2 stops14h 05m

Chicago O'Hare Intl

Tue 15/9

3:40 p.m.-11:12 p.m.

1 stop9h 32m

C$ 580

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 11/9

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

1 stop8h 35m

Chicago O'Hare Intl

Tue 15/9

11:30 a.m.-10:05 p.m.

2 stops12h 35m

C$ 632

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 20/10

6:05 a.m.-6:37 p.m.

2 stops10h 32m

Chicago Midway

Sat 24/10

12:30 p.m.-11:30 p.m.

2 stops13h 00m

C$ 639

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 11/6

12:50 p.m.-9:35 a.m.

2 stops18h 45m

Chicago Midway

Mon 15/6

10:15 a.m.-7:00 a.m.

3 stops22h 45m

C$ 942

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 24/7

12:50 p.m.-9:40 a.m.

2 stops18h 50m

Chicago Midway

Sat 8/8

9:59 a.m.-11:55 a.m.

3 stops27h 56m

C$ 947

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?

What is the cheapest month to fly to Chicago?

The month of January is another great option to travel to Chicago, with average flight prices from Kelowna averaging around C$ 0.

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.
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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 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
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