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Cheap flights from Chicago to Kelowna from $186

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 9/20. 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
0 bags

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Find the cheapest flights from Chicago to Kelowna

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
5:30 pm - 11:50 pm
ORD
-
YLW
8h 20m
1 stop
Multiple Airlines Logo
3:07 pm - 11:59 pm
YLW
-
ORD
6h 52m
1 stop
$478Multiple Airlines
Sat, Sep 5 - Sat, Sep 12
WestJet Logo
5:30 pm - 11:50 pm
ORD
-
YLW
8h 20m
1 stop
WestJet Logo
8:15 pm - 4:40 pm
YLW
-
ORD
18h 25m
1 stop
$488WestJet
Tue, Sep 22 - Wed, Sep 23
Alaska Airlines Logo
8:00 am - 2:17 pm
ORD
-
YLW
8h 17m
1 stop
Alaska Airlines Logo
3:07 pm - 11:59 pm
YLW
-
ORD
6h 52m
1 stop
$502Alaska Airlines
Tue, Sep 22 - Wed, Sep 23
WestJet Logo
5:30 pm - 9:45 am
ORD
-
YLW
18h 15m
2 stops
WestJet Logo
7:05 pm - 4:40 pm
YLW
-
ORD
19h 35m
1 stop
$518WestJet
Sat, Sep 5 - Sat, Sep 12
WestJet Logo
5:30 pm - 8:20 am
ORD
-
YLW
16h 50m
1 stop
WestJet Logo
6:35 pm - 4:40 pm
YLW
-
ORD
20h 05m
2 stops
$530WestJet
Tue, Aug 11 - Sun, Aug 16
WestJet Logo
5:30 pm - 6:00 pm
ORD
-
YLW
26h 30m
2 stops
WestJet Logo
6:35 pm - 4:40 pm
YLW
-
ORD
20h 05m
2 stops
$537WestJet
Tue, Aug 11 - Sun, Aug 16
WestJet Logo
5:30 pm - 8:20 am
ORD
-
YLW
16h 50m
1 stop
WestJet Logo
3:15 pm - 4:40 pm
YLW
-
ORD
23h 25m
1 stop
$539WestJet
Tue, Aug 11 - Sun, Aug 16
Alaska Airlines Logo
9:00 am - 2:09 pm
ORD
-
YLW
7h 09m
1 stop
Alaska Airlines Logo
2:59 pm - 11:59 pm
YLW
-
ORD
7h 00m
1 stop
$559Alaska Airlines
Sun, Aug 23 - Thu, Aug 27
Porter Airlines Logo
10:20 am - 9:52 pm
MDW
-
YLW
13h 32m
1 stop
Porter Airlines Logo
12:50 pm - 9:40 am
YLW
-
MDW
18h 50m
2 stops
$734Porter Airlines
Sun, Jul 19 - Tue, Jul 28
Porter Airlines Logo
10:20 am - 9:52 pm
MDW
-
YLW
13h 32m
1 stop
Porter Airlines Logo
10:50 pm - 2:35 pm
YLW
-
MDW
13h 45m
1 stop
$814Porter Airlines
Sun, Jul 19 - Mon, Jul 20

WestJet flights from Chicago to Kelowna

Our best WestJet deals on Chicago to Kelowna flight tickets
WestJet
Sep 22
ORD5:30 pmChicago O'Hare Intl
8h 20m
1 stop
YLW11:50 pmKelowna
Sep 23
YLW8:15 pmKelowna
18h 25m
1 stop
ORD4:40 pmChicago O'Hare Intl
$488
WestJet
Sep 5
ORD5:30 pmChicago O'Hare Intl
18h 15m
2 stops
YLW9:45 amKelowna
Sep 12
YLW7:05 pmKelowna
19h 35m
1 stop
ORD4:40 pmChicago O'Hare Intl
$518
WestJet
Aug 11
ORD5:30 pmChicago O'Hare Intl
16h 50m
1 stop
YLW8:20 amKelowna
Aug 16
YLW6:35 pmKelowna
20h 05m
2 stops
ORD4:40 pmChicago O'Hare Intl
$530

Alaska Airlines flights from Chicago to Kelowna

Our best Alaska Airlines deals on Chicago to Kelowna flight tickets
Alaska Airlines
Sep 22
ORD8:00 amChicago O'Hare Intl
8h 17m
1 stop
YLW2:17 pmKelowna
Sep 23
YLW3:07 pmKelowna
6h 52m
1 stop
ORD11:59 pmChicago O'Hare Intl
$502
Alaska Airlines
Aug 23
ORD9:00 amChicago O'Hare Intl
7h 09m
1 stop
YLW2:09 pmKelowna
Aug 27
YLW2:59 pmKelowna
7h 00m
1 stop
ORD11:59 pmChicago O'Hare Intl
$559
Alaska Airlines
Sep 5
ORD2:22 pmChicago O'Hare Intl
25h 47m
2 stops
YLW2:09 pmKelowna
Sep 12
YLW3:07 pmKelowna
20h 19m
2 stops
ORD1:26 pmChicago O'Hare Intl
$560

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 832,500 searches. Data last updated May 26, 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

Sat 9/5

5:30 pm-11:50 pm

1 stop8h 20m

Kelowna

Sat 9/12

3:07 pm-11:59 pm

1 stop6h 52m

$478

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 9/22

5:30 pm-11:50 pm

1 stop8h 20m

Kelowna

Wed 9/23

8:15 pm-4:40 pm

1 stop18h 25m

$488

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 9/22

8:00 am-2:17 pm

1 stop8h 17m

Kelowna

Wed 9/23

3:07 pm-11:59 pm

1 stop6h 52m

$502

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sat 9/5

5:30 pm-9:45 am

2 stops18h 15m

Kelowna

Sat 9/12

7:05 pm-4:40 pm

1 stop19h 35m

$518

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 8/11

5:30 pm-8:20 am

1 stop16h 50m

Kelowna

Sun 8/16

6:35 pm-4:40 pm

2 stops20h 05m

$530

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 8/11

5:30 pm-6:00 pm

2 stops26h 30m

Kelowna

Sun 8/16

6:35 pm-4:40 pm

2 stops20h 05m

$537

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 8/11

5:30 pm-8:20 am

1 stop16h 50m

Kelowna

Sun 8/16

3:15 pm-4:40 pm

1 stop23h 25m

$539
Quickest round-trip

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sun 8/23

9:00 am-2:09 pm

1 stop7h 09m

Kelowna

Thu 8/27

2:59 pm-11:59 pm

1 stop7h 00m

$559

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 7/19

10:20 am-9:52 pm

1 stop13h 32m

Kelowna

Tue 7/28

12:50 pm-9:40 am

2 stops18h 50m

$734

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 7/19

10:20 am-9:52 pm

1 stop13h 32m

Kelowna

Mon 7/20

10:50 pm-2:35 pm

1 stop13h 45m

$814

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 $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 $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 1613.5 mi. Typically, this will take 6h 35m by plane in normal conditions.

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

    Prices for flights from Chicago to Kelowna Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to Kelowna Airport?

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

    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 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.

Best airlines flying from Chicago to Kelowna

Compare and see reviews for airlines that fly from Chicago to Kelowna with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom $140Free CancellationRating
7.1
11,090 reviews
Search Air Canada flights
Alaska AirlinesPriceFrom $342Free CancellationRating
7.9
12,418 reviews
Search Alaska Airlines flights

Traveling to a place near Kelowna?

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

Why use momondo?

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

Finding the right flight to Kelowna from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Kelowna quick and easy, saving you time and money.

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

momondo does allow users to show only those flights to Kelowna from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

momondo helps you find the best flight between Chicago and Kelowna by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Kelowna, momondo offers a useful price alert feature which will track prices for flights to Kelowna from Chicago and alert you when they change.

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