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Cheap flights from Kelowna to Chicago from C$ 290

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 22/9. 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
1 adult, Economy, 0 bags

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  Kelowna-ORD Chicago O'Hare Intl
6h 50m1 stop Calgary
WestJet Logo
5:30 p.m. - 11:50 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
8h 20m1 stop Calgary
C$ 428WestJet
Fri, 25 Sep - Fri, 2 Oct
Air Canada Logo
5:50 a.m. - 2:37 p.m.YLW  Kelowna-ORD Chicago O'Hare Intl
6h 47m1 stop Vancouver Intl
Air Canada Logo
3:30 p.m. - 11:28 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
8h 58m1 stop Vancouver Intl
C$ 471Air Canada
Wed, 28 Oct - Wed, 4 Nov
Delta Logo
7:50 a.m. - 4:40 p.m.YLW  Kelowna-ORD Chicago O'Hare Intl
6h 50m1 stop Calgary
Delta Logo
12:29 p.m. - 11:50 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
13h 21m2 stops Minneapolis St Paul Calgary
C$ 495Delta
Mon, 7 Sep - Sat, 12 Sep
Multiple Airlines Logo
7:50 a.m. - 4:40 p.m.YLW  Kelowna-ORD Chicago O'Hare Intl
6h 50m1 stop Calgary
Multiple Airlines Logo
8:00 a.m. - 2:17 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
8h 17m1 stop Seattle/Tacoma Intl
C$ 549Multiple Airlines
Mon, 7 Sep - Sat, 12 Sep
Multiple Airlines Logo
8:45 p.m. - 4:40 p.m.YLW  Kelowna-ORD Chicago O'Hare Intl
41h 55m2 stops Vancouver Intl Calgary
Multiple Airlines Logo
1:03 p.m. - 2:17 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
27h 14m1 stop Seattle/Tacoma Intl
C$ 563Multiple Airlines
Tue, 8 Sep - Sat, 12 Sep
Air Canada Logo
5:50 a.m. - 2:37 p.m.YLW  Kelowna-ORD Chicago O'Hare Intl
6h 47m1 stop Vancouver Intl
Air Canada Logo
1:00 p.m. - 11:28 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
11h 28m2 stops Denver Intl Vancouver Intl
C$ 576Air Canada
Wed, 28 Oct - Wed, 4 Nov
Multiple Airlines Logo
5:05 a.m. - 5:38 a.m.YLW  Kelowna-ORD Chicago O'Hare Intl
22h 33m2 stops Calgary Las Vegas Harry Reid Intl
Multiple Airlines Logo
6:30 a.m. - 11:50 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
19h 20m3 stops Denver Intl Las Vegas Harry Reid Intl Calgary
C$ 577Multiple Airlines
Sat, 12 Sep - Sat, 19 Sep
Air Canada Logo
10:50 p.m. - 9:00 a.m.YLW  Kelowna-ORD Chicago O'Hare Intl
8h 10m1 stop Toronto Pearson Intl
Air Canada Logo
3:40 p.m. - 11:12 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
9h 32m1 stop Vancouver Intl
C$ 604Air Canada
Wed, 30 Sep - Sat, 3 Oct
Air Canada Logo
10:50 p.m. - 9:00 a.m.YLW  Kelowna-ORD Chicago O'Hare Intl
8h 10m1 stop Toronto Pearson Intl
Air Canada Logo
2:15 p.m. - 9:57 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
9h 42m1 stop Toronto Pearson Intl
C$ 615Air Canada
Mon, 14 Sep - Tue, 15 Sep
Multiple Airlines Logo
5:05 a.m. - 12:23 a.m.YLW  Kelowna-ORD Chicago O'Hare Intl
17h 18m3 stops Calgary Las Vegas Harry Reid Intl Denver Intl
Multiple Airlines Logo
6:30 a.m. - 11:50 p.m.ORD  Chicago O'Hare Intl-YLW Kelowna
19h 20m3 stops Denver Intl Las Vegas Harry Reid Intl Calgary
C$ 620Multiple Airlines
Sat, 12 Sep - Sat, 19 Sep

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Air Canada flights from Kelowna to Chicago

Our best Air Canada deals on Kelowna to Chicago flight tickets
Air Canada
28 Oct
YLW5:50 a.m.Kelowna
6h 47m
1 stop
ORD2:37 p.m.Chicago O'Hare Intl
4 Nov
ORD3:30 p.m.Chicago O'Hare Intl
8h 58m
1 stop
YLW11:28 p.m.Kelowna
C$ 471
Air Canada
28 Oct
YLW5:50 a.m.Kelowna
6h 47m
1 stop
ORD2:37 p.m.Chicago O'Hare Intl
4 Nov
ORD1:00 p.m.Chicago O'Hare Intl
11h 28m
2 stops
YLW11:28 p.m.Kelowna
C$ 576
Air Canada
30 Sep
YLW10:50 p.m.Kelowna
8h 10m
1 stop
ORD9:00 a.m.Chicago O'Hare Intl
3 Oct
ORD3:40 p.m.Chicago O'Hare Intl
9h 32m
1 stop
YLW11:12 p.m.Kelowna
C$ 604

Delta flights from Kelowna to Chicago

Our best Delta deals on Kelowna to Chicago flight tickets
Delta
7 Sep
YLW7:50 a.m.Kelowna
6h 50m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
12 Sep
ORD12:29 p.m.Chicago O'Hare Intl
13h 21m
2 stops
YLW11:50 p.m.Kelowna
C$ 495
Delta
28 Oct
YLW10:35 a.m.Kelowna
9h 25m
2 stops
ORD10:00 p.m.Chicago O'Hare Intl
4 Nov
ORD12:29 p.m.Chicago O'Hare Intl
13h 24m
2 stops
YLW12:53 a.m.Kelowna
C$ 650
Delta
30 Sep
YLW1:00 p.m.Kelowna
8h 57m
2 stops
ORD11:57 p.m.Chicago O'Hare Intl
3 Oct
ORD2:00 p.m.Chicago O'Hare Intl
10h 05m
2 stops
YLW10:05 p.m.Kelowna
C$ 820

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 14 August 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 Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Fri 25/9

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

1 stop6h 50m

Chicago O'Hare Intl

Fri 2/10

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

1 stop8h 20m

C$ 428

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Wed 28/10

5:50 a.m.-2:37 p.m.

1 stop6h 47m

Chicago O'Hare Intl

Wed 4/11

3:30 p.m.-11:28 p.m.

1 stop8h 58m

C$ 471

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Mon 7/9

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

1 stop6h 50m

Chicago O'Hare Intl

Sat 12/9

12:29 p.m.-11:50 p.m.

2 stops13h 21m

C$ 495
Quickest round-trip

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Mon 7/9

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

1 stop6h 50m

Chicago O'Hare Intl

Sat 12/9

8:00 a.m.-2:17 p.m.

1 stop8h 17m

C$ 549

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Tue 8/9

8:45 p.m.-4:40 p.m.

2 stops41h 55m

Chicago O'Hare Intl

Sat 12/9

1:03 p.m.-2:17 p.m.

1 stop27h 14m

C$ 563

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Wed 28/10

5:50 a.m.-2:37 p.m.

1 stop6h 47m

Chicago O'Hare Intl

Wed 4/11

1:00 p.m.-11:28 p.m.

2 stops11h 28m

C$ 576

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Sat 12/9

5:05 a.m.-5:38 a.m.

2 stops22h 33m

Chicago O'Hare Intl

Sat 19/9

6:30 a.m.-11:50 p.m.

3 stops19h 20m

C$ 577

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Wed 30/9

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

1 stop8h 10m

Chicago O'Hare Intl

Sat 3/10

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

1 stop9h 32m

C$ 604

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Mon 14/9

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

1 stop8h 10m

Chicago O'Hare Intl

Tue 15/9

2:15 p.m.-9:57 p.m.

1 stop9h 42m

C$ 615

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Sat 12/9

5:05 a.m.-12:23 a.m.

3 stops17h 18m

Chicago O'Hare Intl

Sat 19/9

6:30 a.m.-11:50 p.m.

3 stops19h 20m

C$ 620

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?

Prices are currently low for flights on this route.

Typical prices usually range from C$ 507 to C$ 567.
The lowest price recently found on this route was C$ 428.

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.
Search flight deals

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
Valparaiso
Portage

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