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Cheap flights from Chicago to Kelowna from $140

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 9/28. 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

Discover deals from 900+ travel sites with momondo.

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 pm - 10:05 pmORD  Chicago O'Hare Intl-YLW Kelowna
6h 35m1 stop Calgary
WestJet Logo
7:50 am - 4:40 pmYLW  Kelowna-ORD Chicago O'Hare Intl
6h 50m1 stop Calgary
$285WestJet
Mon, Sep 28 - Mon, Oct 5
WestJet Logo
5:30 pm - 10:05 pmORD  Chicago O'Hare Intl-YLW Kelowna
6h 35m1 stop Calgary
WestJet Logo
7:50 am - 4:40 pmYLW  Kelowna-ORD Chicago O'Hare Intl
6h 50m1 stop Calgary
$289WestJet
Tue, Sep 29 - Tue, Oct 6
WestJet Logo
5:30 pm - 11:50 pmORD  Chicago O'Hare Intl-YLW Kelowna
8h 20m1 stop Calgary
WestJet Logo
7:50 am - 4:40 pmYLW  Kelowna-ORD Chicago O'Hare Intl
6h 50m1 stop Calgary
$297WestJet
Mon, Sep 28 - Mon, Oct 5
Multiple Airlines Logo
5:30 pm - 11:50 pmORD  Chicago O'Hare Intl-YLW Kelowna
8h 20m1 stop Calgary
Multiple Airlines Logo
6:05 pm - 9:00 amYLW  Kelowna-ORD Chicago O'Hare Intl
12h 55m2 stops Vancouver Intl Toronto Pearson Intl
$315Multiple Airlines
Mon, Sep 28 - Mon, Oct 5
Multiple Airlines Logo
5:30 pm - 10:05 pmORD  Chicago O'Hare Intl-YLW Kelowna
6h 35m1 stop Calgary
Multiple Airlines Logo
8:15 pm - 6:23 pmYLW  Kelowna-ORD Chicago O'Hare Intl
20h 08m2 stops Calgary Atlanta Hartsfield-Jackson
$315Multiple Airlines
Sun, Sep 13 - Fri, Sep 18
WestJet Logo
5:30 pm - 10:05 pmORD  Chicago O'Hare Intl-YLW Kelowna
6h 35m1 stop Calgary
WestJet Logo
7:50 am - 4:40 pmYLW  Kelowna-ORD Chicago O'Hare Intl
6h 50m1 stop Calgary
$316WestJet
Sun, Sep 27 - Sun, Oct 4
Multiple Airlines Logo
7:28 pm - 2:35 pmORD  Chicago O'Hare Intl-YLW Kelowna
21h 07m2 stops Atlanta Hartsfield-Jackson Vancouver Intl
Multiple Airlines Logo
7:50 am - 4:40 pmYLW  Kelowna-ORD Chicago O'Hare Intl
6h 50m1 stop Calgary
$318Multiple Airlines
Tue, Sep 29 - Tue, Oct 6
Air Canada Logo
9:55 am - 6:55 pmORD  Chicago O'Hare Intl-YLW Kelowna
11h 00m2 stops Toronto Pearson Intl Calgary
Air Canada Logo
7:25 pm - 9:00 amYLW  Kelowna-ORD Chicago O'Hare Intl
11h 35m2 stops Vancouver Intl Toronto Pearson Intl
$327Air Canada
Mon, Sep 28 - Mon, Oct 5
Air Canada Logo
9:55 am - 6:55 pmORD  Chicago O'Hare Intl-YLW Kelowna
11h 00m2 stops Toronto Pearson Intl Calgary
Air Canada Logo
7:25 pm - 9:00 amYLW  Kelowna-ORD Chicago O'Hare Intl
11h 35m2 stops Vancouver Intl Toronto Pearson Intl
$329Air Canada
Mon, Sep 28 - Mon, Oct 5
Air Canada Logo
3:40 pm - 11:32 pmORD  Chicago O'Hare Intl-YLW Kelowna
9h 52m1 stop Vancouver Intl
Air Canada Logo
10:50 pm - 9:00 amYLW  Kelowna-ORD Chicago O'Hare Intl
8h 10m1 stop Toronto Pearson Intl
$366Air Canada
Thu, Sep 24 - Mon, Sep 28

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Porter Airlines flights from Chicago to Kelowna

Our best Porter Airlines deals on Chicago to Kelowna flight tickets
Porter Airlines
Sep 24
MDW11:45 amChicago Midway
12h 07m
1 stop
YLW9:52 pmKelowna
Sep 28
YLW10:50 pmKelowna
13h 45m
1 stop
MDW2:35 pmChicago Midway
$505
Porter Airlines
Sep 10
MDW3:20 pmChicago Midway
22h 35m
2 stops
YLW11:55 amKelowna
Sep 16
YLW12:50 pmKelowna
23h 45m
2 stops
MDW2:35 pmChicago Midway
$766
Porter Airlines
Sep 10
MDW3:20 pmChicago Midway
22h 35m
2 stops
YLW11:55 amKelowna
Sep 17
YLW12:50 pmKelowna
20h 10m
2 stops
MDW11:00 amChicago Midway
$968

WestJet flights from Chicago to Kelowna

Our best WestJet deals on Chicago to Kelowna flight tickets
WestJet
Sep 28
ORD5:30 pmChicago O'Hare Intl
6h 35m
1 stop
YLW10:05 pmKelowna
Oct 5
YLW7:50 amKelowna
6h 50m
1 stop
ORD4:40 pmChicago O'Hare Intl
$285
WestJet
Sep 29
ORD5:30 pmChicago O'Hare Intl
6h 35m
1 stop
YLW10:05 pmKelowna
Oct 6
YLW7:50 amKelowna
6h 50m
1 stop
ORD4:40 pmChicago O'Hare Intl
$289
WestJet
Sep 28
ORD5:30 pmChicago O'Hare Intl
8h 20m
1 stop
YLW11:50 pmKelowna
Oct 5
YLW7:50 amKelowna
6h 50m
1 stop
ORD4:40 pmChicago O'Hare Intl
$297

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 August 15, 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
Quickest round-trip

ChicagoKelowna

ORD Chicago O'Hare Intl - YLW Kelowna

ORDYLW

Chicago O'Hare Intl

Mon 9/28

5:30 pm-10:05 pm

1 stop6h 35m

Kelowna

Mon 10/5

7:50 am-4:40 pm

1 stop6h 50m

$285

ChicagoKelowna

ORD Chicago O'Hare Intl - YLW Kelowna

ORDYLW

Chicago O'Hare Intl

Tue 9/29

5:30 pm-10:05 pm

1 stop6h 35m

Kelowna

Tue 10/6

7:50 am-4:40 pm

1 stop6h 50m

$289

ChicagoKelowna

ORD Chicago O'Hare Intl - YLW Kelowna

ORDYLW

Chicago O'Hare Intl

Mon 9/28

5:30 pm-11:50 pm

1 stop8h 20m

Kelowna

Mon 10/5

7:50 am-4:40 pm

1 stop6h 50m

$297

ChicagoKelowna

ORD Chicago O'Hare Intl - YLW Kelowna

ORDYLW

Chicago O'Hare Intl

Mon 9/28

5:30 pm-11:50 pm

1 stop8h 20m

Kelowna

Mon 10/5

6:05 pm-9:00 am

2 stops12h 55m

$315

ChicagoKelowna

ORD Chicago O'Hare Intl - YLW Kelowna

ORDYLW

Chicago O'Hare Intl

Sun 9/13

5:30 pm-10:05 pm

1 stop6h 35m

Kelowna

Fri 9/18

8:15 pm-6:23 pm

2 stops20h 08m

$315

ChicagoKelowna

ORD Chicago O'Hare Intl - YLW Kelowna

ORDYLW

Chicago O'Hare Intl

Sun 9/27

5:30 pm-10:05 pm

1 stop6h 35m

Kelowna

Sun 10/4

7:50 am-4:40 pm

1 stop6h 50m

$316

ChicagoKelowna

ORD Chicago O'Hare Intl - YLW Kelowna

ORDYLW

Chicago O'Hare Intl

Tue 9/29

7:28 pm-2:35 pm

2 stops21h 07m

Kelowna

Tue 10/6

7:50 am-4:40 pm

1 stop6h 50m

$318

ChicagoKelowna

ORD Chicago O'Hare Intl - YLW Kelowna

ORDYLW

Chicago O'Hare Intl

Mon 9/28

9:55 am-6:55 pm

2 stops11h 00m

Kelowna

Mon 10/5

7:25 pm-9:00 am

2 stops11h 35m

$327

ChicagoKelowna

ORD Chicago O'Hare Intl - YLW Kelowna

ORDYLW

Chicago O'Hare Intl

Mon 9/28

9:55 am-6:55 pm

2 stops11h 00m

Kelowna

Mon 10/5

7:25 pm-9:00 am

2 stops11h 35m

$329

ChicagoKelowna

ORD Chicago O'Hare Intl - YLW Kelowna

ORDYLW

Chicago O'Hare Intl

Thu 9/24

3:40 pm-11:32 pm

1 stop9h 52m

Kelowna

Mon 9/28

10:50 pm-9:00 am

1 stop8h 10m

$366

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
11,478 reviews
Search Air Canada flights
WestJetPriceFrom $178Free CancellationRating
7.2
3,433 reviews
Search WestJet 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.

An easier way to manage your Kelowna trip

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