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Cheap flights from Chicago to Kelowna from C$ 286

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Kelowna departing on 4/8. 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 Chicago to Kelowna

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
5:30 p.m. - 9:45 a.m.
ORD
-
YLW
18h 15m
2 stops
WestJet Logo
7:50 a.m. - 4:40 p.m.
YLW
-
ORD
6h 50m
1 stop
C$ 493WestJet
Sun, 24 May - Sat, 30 May
Multiple Airlines Logo
5:30 p.m. - 11:50 p.m.
ORD
-
YLW
8h 20m
1 stop
Multiple Airlines Logo
3:36 p.m. - 5:00 a.m.
YLW
-
ORD
11h 24m
2 stops
C$ 558Multiple Airlines
Tue, 2 Jun - Tue, 9 Jun
Multiple Airlines Logo
5:30 p.m. - 9:45 a.m.
ORD
-
YLW
18h 15m
2 stops
Multiple Airlines Logo
5:05 a.m. - 7:40 p.m.
YLW
-
ORD
12h 35m
3 stops
C$ 560Multiple Airlines
Sun, 24 May - Sat, 30 May
WestJet Logo
5:30 p.m. - 11:50 p.m.
ORD
-
YLW
8h 20m
1 stop
WestJet Logo
12:05 p.m. - 4:40 p.m.
YLW
-
ORD
26h 35m
1 stop
C$ 564WestJet
Tue, 2 Jun - Tue, 9 Jun
WestJet Logo
5:30 p.m. - 3:45 p.m.
ORD
-
YLW
24h 15m
2 stops
WestJet Logo
7:50 a.m. - 4:40 p.m.
YLW
-
ORD
6h 50m
1 stop
C$ 571WestJet
Mon, 8 Jun - Fri, 12 Jun
WestJet Logo
5:30 p.m. - 11:50 p.m.
ORD
-
YLW
8h 20m
1 stop
WestJet Logo
6:35 p.m. - 4:40 p.m.
YLW
-
ORD
20h 05m
2 stops
C$ 605WestJet
Tue, 11 Aug - Sun, 16 Aug
Delta Logo
5:30 p.m. - 11:50 p.m.
ORD
-
YLW
8h 20m
1 stop
Delta Logo
6:05 a.m. - 4:40 p.m.
YLW
-
ORD
8h 35m
1 stop
C$ 606Delta
Sun, 24 May - Sat, 30 May
WestJet Logo
5:30 p.m. - 9:45 a.m.
ORD
-
YLW
18h 15m
2 stops
WestJet Logo
6:35 p.m. - 4:40 p.m.
YLW
-
ORD
20h 05m
2 stops
C$ 630WestJet
Tue, 11 Aug - Sun, 16 Aug
Air Canada Logo
3:40 p.m. - 11:12 p.m.
ORD
-
YLW
9h 32m
1 stop
Air Canada Logo
5:25 a.m. - 2:48 p.m.
YLW
-
ORD
7h 23m
1 stop
C$ 633Air Canada
Sat, 26 Sep - Tue, 29 Sep
Air Canada Logo
3:40 p.m. - 11:12 p.m.
ORD
-
YLW
9h 32m
1 stop
Air Canada Logo
11:30 p.m. - 9:00 a.m.
YLW
-
ORD
7h 30m
1 stop
C$ 644Air Canada
Mon, 21 Sep - Fri, 25 Sep

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United Airlines flights from Chicago to Kelowna

Our best United Airlines deals on Chicago to Kelowna flight tickets
United Airlines
26 Sep
ORD5:00 a.m.Chicago O'Hare Intl
9h 17m
2 stops
YLW12:17 p.m.Kelowna
29 Sep
YLW5:25 a.m.Kelowna
16h 09m
2 stops
ORD11:34 p.m.Chicago O'Hare Intl
C$ 813
United Airlines
26 Sep
ORD7:15 a.m.Chicago O'Hare Intl
8h 57m
2 stops
YLW2:12 p.m.Kelowna
29 Sep
YLW5:25 a.m.Kelowna
16h 32m
2 stops
ORD11:57 p.m.Chicago O'Hare Intl
C$ 814
United Airlines
26 Sep
ORD5:00 a.m.Chicago O'Hare Intl
9h 17m
2 stops
YLW12:17 p.m.Kelowna
29 Sep
YLW5:25 a.m.Kelowna
12h 18m
2 stops
ORD7:43 p.m.Chicago O'Hare Intl
C$ 945

WestJet flights from Chicago to Kelowna

Our best WestJet deals on Chicago to Kelowna flight tickets
WestJet
24 May
ORD5:30 p.m.Chicago O'Hare Intl
18h 15m
2 stops
YLW9:45 a.m.Kelowna
30 May
YLW7:50 a.m.Kelowna
6h 50m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 493
WestJet
2 Jun
ORD5:30 p.m.Chicago O'Hare Intl
8h 20m
1 stop
YLW11:50 p.m.Kelowna
9 Jun
YLW12:05 p.m.Kelowna
26h 35m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 564
WestJet
8 Jun
ORD5:30 p.m.Chicago O'Hare Intl
24h 15m
2 stops
YLW3:45 p.m.Kelowna
12 Jun
YLW7:50 a.m.Kelowna
6h 50m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 571

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Kelowna 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 Chicago to Kelowna that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sun 24/5

5:30 p.m.-9:45 a.m.

2 stops18h 15m

Kelowna

Sat 30/5

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

1 stop6h 50m

C$ 493

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 2/6

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

1 stop8h 20m

Kelowna

Tue 9/6

3:36 p.m.-5:00 a.m.

2 stops11h 24m

C$ 558

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sun 24/5

5:30 p.m.-9:45 a.m.

2 stops18h 15m

Kelowna

Sat 30/5

5:05 a.m.-7:40 p.m.

3 stops12h 35m

C$ 560

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 2/6

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

1 stop8h 20m

Kelowna

Tue 9/6

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

1 stop26h 35m

C$ 564

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Mon 8/6

5:30 p.m.-3:45 p.m.

2 stops24h 15m

Kelowna

Fri 12/6

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

1 stop6h 50m

C$ 571

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 11/8

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

1 stop8h 20m

Kelowna

Sun 16/8

6:35 p.m.-4:40 p.m.

2 stops20h 05m

C$ 605
Quickest round-trip

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sun 24/5

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

1 stop8h 20m

Kelowna

Sat 30/5

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

1 stop8h 35m

C$ 606

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 11/8

5:30 p.m.-9:45 a.m.

2 stops18h 15m

Kelowna

Sun 16/8

6:35 p.m.-4:40 p.m.

2 stops20h 05m

C$ 630

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sat 26/9

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

1 stop9h 32m

Kelowna

Tue 29/9

5:25 a.m.-2:48 p.m.

1 stop7h 23m

C$ 633

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Mon 21/9

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

1 stop9h 32m

Kelowna

Fri 25/9

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

1 stop7h 30m

C$ 644

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 Kelowna from

How to get the cheapest flight ticket from Chicago to Kelowna

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 month to fly to Kelowna?

The cheapest month to fly to Kelowna from Chicago is in November. Flight prices, which tend to average around C$ 0, are often lower during this time because this is during the off-season. If you don’t want to visit Kelowna in November, then you should wait until April to fly from Chicago, when ticket prices are also cheap, with an average price of C$ 0.

When to book flights from Chicago to Kelowna

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Kelowna according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Kelowna (CHI to YLW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Kelowna

Fastest flight time

8h 20m

Direct flights

None
The fastest flight from Chicago to Kelowna takes 8h 20m
There are no direct flights from Chicago to Kelowna. There are no popular flight routes from Chicago to Kelowna.
Search flight deals

Frequently asked questions about flying from Chicago to Kelowna

  • How far is Chicago to Kelowna by plane?

    A flight from Chicago to Kelowna will travel around 2596.6 km. Flights usually cover this in 8h 20m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago to Kelowna Airport?

    Prices for flights from Chicago to Kelowna Airport are updated daily.

  • How old do you have to be to fly from Chicago to Kelowna Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Kelowna Airport.

  • What documentation or ID do you need to fly to Kelowna Airport?

    The necessary travel and health documents for your Kelowna Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Travelling to a place near Kelowna?

Book flights to Kelowna if you plan to visit one of these locations
Revelstoke
Vernon
West Kelowna
Salmon Arm

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Kelowna?

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 Chicago to Kelowna for you.

Can I find flights from Chicago to Kelowna with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Kelowna from Chicago with this policy.

How can momondo help me find flights from Chicago to Kelowna?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Kelowna.

I’m not ready to book a flight from Chicago to Kelowna right now. Can momondo alert me if prices change?

Price alerts on flights to Kelowna from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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