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Cheap flights from Chicago to Kelowna from C$ 253

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 12/11. 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 Chicago to Kelowna

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:00 a.m. - 12:57 p.m.
ORD
-
YLW
8h 57m
1 stop
Multiple Airlines Logo
5:20 a.m. - 1:35 p.m.
YLW
-
ORD
6h 15m
1 stop
C$ 508Multiple Airlines
Wed, 21 Oct - Mon, 26 Oct
WestJet Logo
5:30 p.m. - 11:50 p.m.
ORD
-
YLW
8h 20m
1 stop
WestJet Logo
6:05 a.m. - 4:40 p.m.
YLW
-
ORD
8h 35m
1 stop
C$ 522WestJet
Thu, 24 Sep - Mon, 28 Sep
WestJet Logo
5:30 p.m. - 10:05 p.m.
ORD
-
YLW
6h 35m
1 stop
WestJet Logo
7:50 a.m. - 4:40 p.m.
YLW
-
ORD
6h 50m
1 stop
C$ 525WestJet
Thu, 1 Oct - Mon, 5 Oct
WestJet Logo
5:30 p.m. - 10:05 p.m.
ORD
-
YLW
6h 35m
1 stop
WestJet Logo
7:50 a.m. - 4:40 p.m.
YLW
-
ORD
6h 50m
1 stop
C$ 526WestJet
Thu, 1 Oct - Mon, 5 Oct
WestJet Logo
5:30 p.m. - 10:05 p.m.
ORD
-
YLW
6h 35m
1 stop
WestJet Logo
7:50 a.m. - 4:40 p.m.
YLW
-
ORD
6h 50m
1 stop
C$ 570WestJet
Sat, 8 Aug - Sat, 15 Aug
Air Canada Logo
3:40 p.m. - 11:27 p.m.
ORD
-
YLW
9h 47m
1 stop
Air Canada Logo
5:25 a.m. - 2:43 p.m.
YLW
-
ORD
7h 18m
1 stop
C$ 600Air Canada
Sat, 19 Sep - Sat, 26 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$ 607Air Canada
Wed, 30 Sep - Mon, 5 Oct
Delta Logo
1:19 p.m. - 10:05 p.m.
MDW
-
YLW
10h 46m
2 stops
Delta Logo
8:15 p.m. - 11:55 a.m.
YLW
-
MDW
13h 40m
2 stops
C$ 1,006Delta
Thu, 24 Sep - Mon, 28 Sep
Delta Logo
2:00 p.m. - 11:50 p.m.
MDW
-
YLW
11h 50m
2 stops
Delta Logo
8:15 p.m. - 11:55 a.m.
YLW
-
MDW
13h 40m
2 stops
C$ 1,023Delta
Thu, 24 Sep - Mon, 28 Sep
Porter Airlines Logo
3:20 p.m. - 11:55 a.m.
MDW
-
YLW
22h 35m
2 stops
Porter Airlines Logo
12:50 p.m. - 9:40 a.m.
YLW
-
MDW
18h 50m
2 stops
C$ 1,128Porter Airlines
Fri, 17 Jul - Fri, 24 Jul

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Air Canada flights from Chicago to Kelowna

Our best Air Canada deals on Chicago to Kelowna flight tickets
Air Canada
19 Sep
ORD3:40 p.m.Chicago O'Hare Intl
9h 47m
1 stop
YLW11:27 p.m.Kelowna
26 Sep
YLW5:25 a.m.Kelowna
7h 18m
1 stop
ORD2:43 p.m.Chicago O'Hare Intl
C$ 600
Air Canada
30 Sep
ORD3:40 p.m.Chicago O'Hare Intl
9h 32m
1 stop
YLW11:12 p.m.Kelowna
5 Oct
YLW11:30 p.m.Kelowna
7h 30m
1 stop
ORD9:00 a.m.Chicago O'Hare Intl
C$ 607
Air Canada
30 Sep
ORD3:40 p.m.Chicago O'Hare Intl
9h 47m
1 stop
YLW11:27 p.m.Kelowna
5 Oct
YLW11:30 p.m.Kelowna
7h 30m
1 stop
ORD9:00 a.m.Chicago O'Hare Intl
C$ 611

Delta flights from Chicago to Kelowna

Our best Delta deals on Chicago to Kelowna flight tickets
Delta
1 Oct
ORD12:40 p.m.Chicago O'Hare Intl
13h 10m
2 stops
YLW11:50 p.m.Kelowna
5 Oct
YLW6:05 a.m.Kelowna
12h 17m
2 stops
ORD8:22 p.m.Chicago O'Hare Intl
C$ 743
Delta
1 Oct
ORD12:40 p.m.Chicago O'Hare Intl
13h 10m
2 stops
YLW11:50 p.m.Kelowna
5 Oct
YLW6:05 a.m.Kelowna
12h 17m
2 stops
ORD8:22 p.m.Chicago O'Hare Intl
C$ 744
Delta
24 Sep
MDW1:19 p.m.Chicago Midway
10h 46m
2 stops
YLW10:05 p.m.Kelowna
28 Sep
YLW8:15 p.m.Kelowna
13h 40m
2 stops
MDW11:55 a.m.Chicago Midway
C$ 1,006

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 21 June 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

Wed 21/10

6:00 a.m.-12:57 p.m.

1 stop8h 57m

Kelowna

Mon 26/10

5:20 a.m.-1:35 p.m.

1 stop6h 15m

C$ 508

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Thu 24/9

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

1 stop8h 20m

Kelowna

Mon 28/9

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

1 stop8h 35m

C$ 522
Quickest round-trip

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Thu 1/10

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

1 stop6h 35m

Kelowna

Mon 5/10

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

1 stop6h 50m

C$ 525

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Thu 1/10

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

1 stop6h 35m

Kelowna

Mon 5/10

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

1 stop6h 50m

C$ 526

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sat 8/8

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

1 stop6h 35m

Kelowna

Sat 15/8

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

1 stop6h 50m

C$ 570

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sat 19/9

3:40 p.m.-11:27 p.m.

1 stop9h 47m

Kelowna

Sat 26/9

5:25 a.m.-2:43 p.m.

1 stop7h 18m

C$ 600

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Wed 30/9

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

1 stop9h 32m

Kelowna

Mon 5/10

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

1 stop7h 30m

C$ 607

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 24/9

1:19 p.m.-10:05 p.m.

2 stops10h 46m

Kelowna

Mon 28/9

8:15 p.m.-11:55 a.m.

2 stops13h 40m

C$ 1,006

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 24/9

2:00 p.m.-11:50 p.m.

2 stops11h 50m

Kelowna

Mon 28/9

8:15 p.m.-11:55 a.m.

2 stops13h 40m

C$ 1,023

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 17/7

3:20 p.m.-11:55 a.m.

2 stops22h 35m

Kelowna

Fri 24/7

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

2 stops18h 50m

C$ 1,128

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

6h 35m

Direct flights

None
The fastest flight from Chicago to Kelowna takes 6h 35m
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 6h 35m, 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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