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Cheap flights from Kelowna to Chicago from C$ 287

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 17/8. 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

Find the cheapest flights from Kelowna to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
12:05 p.m. - 4:40 p.m.
YLW
-
ORD
26h 35m
1 stop
WestJet Logo
5:30 p.m. - 10:05 p.m.
ORD
-
YLW
6h 35m
1 stop
C$ 556WestJet
Sat, 29 Aug - Wed, 2 Sep
WestJet Logo
8:45 p.m. - 4:40 p.m.
YLW
-
ORD
17h 55m
2 stops
WestJet Logo
5:30 p.m. - 1:20 p.m.
ORD
-
YLW
21h 50m
1 stop
C$ 598WestJet
Sat, 29 Aug - Wed, 2 Sep
Delta Logo
6:05 a.m. - 6:31 p.m.
YLW
-
MDW
10h 26m
2 stops
Delta Logo
1:00 p.m. - 11:50 p.m.
MDW
-
YLW
12h 50m
2 stops
C$ 639Delta
Fri, 11 Sep - Tue, 15 Sep
United Airlines Logo
5:25 a.m. - 10:58 p.m.
YLW
-
ORD
15h 33m
2 stops
United Airlines Logo
5:00 a.m. - 11:14 p.m.
ORD
-
YLW
20h 14m
2 stops
C$ 688United Airlines
Sat, 29 Aug - Wed, 2 Sep
United Airlines Logo
11:00 p.m. - 1:22 p.m.
YLW
-
ORD
12h 22m
1 stop
United Airlines Logo
7:09 a.m. - 10:01 p.m.
ORD
-
YLW
16h 52m
1 stop
C$ 783United Airlines
Fri, 31 Jul - Fri, 7 Aug
Multiple Airlines Logo
9:05 p.m. - 4:40 p.m.
YLW
-
ORD
41h 35m
2 stops
Multiple Airlines Logo
5:30 p.m. - 8:20 p.m.
ORD
-
YLW
28h 50m
1 stop
C$ 801Multiple Airlines
Mon, 18 May - Sat, 23 May
United Airlines Logo
8:30 p.m. - 5:40 a.m.
YLW
-
ORD
7h 10m
1 stop
United Airlines Logo
5:00 a.m. - 5:29 p.m.
ORD
-
YLW
14h 29m
2 stops
C$ 806United Airlines
Tue, 7 Jul - Thu, 9 Jul
Air Canada Logo
7:25 p.m. - 5:40 a.m.
YLW
-
ORD
8h 15m
1 stop
Air Canada Logo
7:45 p.m. - 10:29 a.m.
ORD
-
YLW
16h 44m
1 stop
C$ 844Air Canada
Tue, 7 Jul - Thu, 9 Jul
Delta Logo
6:05 a.m. - 6:31 p.m.
YLW
-
MDW
10h 26m
2 stops
Delta Logo
1:00 p.m. - 11:50 p.m.
MDW
-
YLW
12h 50m
2 stops
C$ 891Delta
Fri, 11 Sep - Tue, 15 Sep
Multiple Airlines Logo
12:50 p.m. - 9:40 a.m.
YLW
-
MDW
18h 50m
2 stops
Multiple Airlines Logo
1:49 p.m. - 11:15 a.m.
MDW
-
YLW
23h 26m
3 stops
C$ 1,099Multiple Airlines
Tue, 7 Jul - Thu, 9 Jul

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United Airlines flights from Kelowna to Chicago

Our best United Airlines deals on Kelowna to Chicago flight tickets
United Airlines
29 Aug
YLW5:25 a.m.Kelowna
15h 33m
2 stops
ORD10:58 p.m.Chicago O'Hare Intl
2 Sep
ORD5:00 a.m.Chicago O'Hare Intl
20h 14m
2 stops
YLW11:14 p.m.Kelowna
C$ 688
United Airlines
31 Jul
YLW11:00 p.m.Kelowna
12h 22m
1 stop
ORD1:22 p.m.Chicago O'Hare Intl
7 Aug
ORD7:09 a.m.Chicago O'Hare Intl
16h 52m
1 stop
YLW10:01 p.m.Kelowna
C$ 783
United Airlines
7 Jul
YLW8:30 p.m.Kelowna
7h 10m
1 stop
ORD5:40 a.m.Chicago O'Hare Intl
9 Jul
ORD5:00 a.m.Chicago O'Hare Intl
14h 29m
2 stops
YLW5:29 p.m.Kelowna
C$ 806

WestJet flights from Kelowna to Chicago

Our best WestJet deals on Kelowna to Chicago flight tickets
WestJet
29 Aug
YLW12:05 p.m.Kelowna
26h 35m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
2 Sep
ORD5:30 p.m.Chicago O'Hare Intl
6h 35m
1 stop
YLW10:05 p.m.Kelowna
C$ 556
WestJet
29 Aug
YLW8:45 p.m.Kelowna
17h 55m
2 stops
ORD4:40 p.m.Chicago O'Hare Intl
2 Sep
ORD5:30 p.m.Chicago O'Hare Intl
21h 50m
1 stop
YLW1:20 p.m.Kelowna
C$ 598
WestJet
29 Aug
YLW6:00 a.m.Kelowna
32h 40m
3 stops
ORD4:40 p.m.Chicago O'Hare Intl
2 Sep
ORD5:30 p.m.Chicago O'Hare Intl
18h 15m
2 stops
YLW9:45 a.m.Kelowna
C$ 839

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 6 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

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sat 29/8

12:05 p.m.-4:40 p.m.

1 stop26h 35m

Chicago O'Hare Intl

Wed 2/9

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

1 stop6h 35m

C$ 556

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sat 29/8

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

2 stops17h 55m

Chicago O'Hare Intl

Wed 2/9

5:30 p.m.-1:20 p.m.

1 stop21h 50m

C$ 598

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 11/9

6:05 a.m.-6:31 p.m.

2 stops10h 26m

Chicago Midway

Tue 15/9

1:00 p.m.-11:50 p.m.

2 stops12h 50m

C$ 639

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sat 29/8

5:25 a.m.-10:58 p.m.

2 stops15h 33m

Chicago O'Hare Intl

Wed 2/9

5:00 a.m.-11:14 p.m.

2 stops20h 14m

C$ 688

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 31/7

11:00 p.m.-1:22 p.m.

1 stop12h 22m

Chicago O'Hare Intl

Fri 7/8

7:09 a.m.-10:01 p.m.

1 stop16h 52m

C$ 783

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 18/5

9:05 p.m.-4:40 p.m.

2 stops41h 35m

Chicago O'Hare Intl

Sat 23/5

5:30 p.m.-8:20 p.m.

1 stop28h 50m

C$ 801
Quickest round-trip

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 7/7

8:30 p.m.-5:40 a.m.

1 stop7h 10m

Chicago O'Hare Intl

Thu 9/7

5:00 a.m.-5:29 p.m.

2 stops14h 29m

C$ 806

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 7/7

7:25 p.m.-5:40 a.m.

1 stop8h 15m

Chicago O'Hare Intl

Thu 9/7

7:45 p.m.-10:29 a.m.

1 stop16h 44m

C$ 844

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 11/9

6:05 a.m.-6:31 p.m.

2 stops10h 26m

Chicago Midway

Tue 15/9

1:00 p.m.-11:50 p.m.

2 stops12h 50m

C$ 891

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 7/7

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

2 stops18h 50m

Chicago Midway

Thu 9/7

1:49 p.m.-11:15 a.m.

3 stops23h 26m

C$ 1,099

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

7h 10m

Direct flights

None
The fastest flight from Kelowna to Chicago takes 7h 10m
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 7h 10m.

  • 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