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Cheap flights from Chicago to Kelowna from $181

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 8/12. 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 pm
ORD
-
YLW
6h 35m
1 stop
WestJet Logo
6:05 am - 4:40 pm
YLW
-
ORD
8h 35m
1 stop
$374WestJet
Wed, Aug 12 - Tue, Sep 22
WestJet Logo
5:30 pm - 10:05 pm
ORD
-
YLW
6h 35m
1 stop
WestJet Logo
7:50 am - 4:40 pm
YLW
-
ORD
6h 50m
1 stop
$378WestJet
Thu, Oct 1 - Mon, Oct 5
Multiple Airlines Logo
7:00 am - 7:00 pm
ORD
-
YLW
14h 00m
2 stops
Multiple Airlines Logo
7:50 am - 4:40 pm
YLW
-
ORD
6h 50m
1 stop
$417Multiple Airlines
Fri, Sep 4 - Sun, Sep 6
Multiple Airlines Logo
7:00 am - 7:00 pm
ORD
-
YLW
14h 00m
2 stops
Multiple Airlines Logo
7:50 am - 4:40 pm
YLW
-
ORD
6h 50m
1 stop
$422Multiple Airlines
Fri, Sep 4 - Sun, Sep 6
Air Canada Logo
3:40 pm - 11:27 pm
ORD
-
YLW
9h 47m
1 stop
Air Canada Logo
5:25 am - 2:43 pm
YLW
-
ORD
7h 18m
1 stop
$424Air Canada
Mon, Sep 28 - Thu, Oct 1
Air Canada Logo
3:40 pm - 11:27 pm
ORD
-
YLW
9h 47m
1 stop
Air Canada Logo
5:25 am - 2:43 pm
YLW
-
ORD
7h 18m
1 stop
$435Air Canada
Mon, Sep 28 - Thu, Oct 1
Porter Airlines Logo
10:25 am - 9:52 pm
MDW
-
YLW
13h 27m
1 stop
Porter Airlines Logo
10:50 pm - 2:35 pm
YLW
-
MDW
13h 45m
1 stop
$627Porter Airlines
Thu, Aug 13 - Mon, Aug 17
Delta Logo
1:19 pm - 10:05 pm
MDW
-
YLW
10h 46m
2 stops
Delta Logo
8:15 pm - 11:55 am
YLW
-
MDW
13h 40m
2 stops
$738Delta
Thu, Sep 24 - Mon, Sep 28
Porter Airlines Logo
10:25 am - 9:52 pm
MDW
-
YLW
13h 27m
1 stop
Porter Airlines Logo
11:45 am - 9:40 am
YLW
-
MDW
19h 55m
1 stop
$769Porter Airlines
Thu, Aug 13 - Fri, Aug 21
Delta Logo
2:00 pm - 11:50 pm
MDW
-
YLW
11h 50m
2 stops
Delta Logo
6:05 am - 6:33 pm
YLW
-
MDW
10h 28m
2 stops
$902Delta
Thu, Sep 24 - Mon, Sep 28

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WestJet flights from Chicago to Kelowna

Our best WestJet deals on Chicago to Kelowna flight tickets
WestJet
Aug 12
ORD5:30 pmChicago O'Hare Intl
6h 35m
1 stop
YLW10:05 pmKelowna
Sep 22
YLW6:05 amKelowna
8h 35m
1 stop
ORD4:40 pmChicago O'Hare Intl
$374
WestJet
Oct 1
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
$378
WestJet
Sep 24
ORD5:30 pmChicago O'Hare Intl
8h 20m
1 stop
YLW11:50 pmKelowna
Sep 28
YLW10:55 amKelowna
27h 45m
1 stop
ORD4:40 pmChicago O'Hare Intl
$407

Alaska Airlines flights from Chicago to Kelowna

Our best Alaska Airlines deals on Chicago to Kelowna flight tickets
Alaska Airlines
Nov 19
ORD7:00 amChicago O'Hare Intl
9h 46m
1 stop
YLW3:46 pmKelowna
Dec 1
YLW2:37 pmKelowna
7h 22m
1 stop
ORD10:59 pmChicago O'Hare Intl
$480
Alaska Airlines
Jun 29
ORD5:42 pmChicago O'Hare Intl
21h 14m
1 stop
YLW12:56 pmKelowna
Jul 5
YLW1:46 pmKelowna
8h 13m
1 stop
ORD11:59 pmChicago O'Hare Intl
$1,053
Alaska Airlines
Jul 10
ORD6:00 amChicago O'Hare Intl
8h 56m
1 stop
YLW12:56 pmKelowna
Jul 12
YLW1:46 pmKelowna
20h 17m
1 stop
ORD12:03 pmChicago O'Hare Intl
$2,384

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 June 28, 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 8/12

5:30 pm-10:05 pm

1 stop6h 35m

Kelowna

Tue 9/22

6:05 am-4:40 pm

1 stop8h 35m

$374
Quickest round-trip

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Thu 10/1

5:30 pm-10:05 pm

1 stop6h 35m

Kelowna

Mon 10/5

7:50 am-4:40 pm

1 stop6h 50m

$378

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Fri 9/4

7:00 am-7:00 pm

2 stops14h 00m

Kelowna

Sun 9/6

7:50 am-4:40 pm

1 stop6h 50m

$417

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Fri 9/4

7:00 am-7:00 pm

2 stops14h 00m

Kelowna

Sun 9/6

7:50 am-4:40 pm

1 stop6h 50m

$422

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Mon 9/28

3:40 pm-11:27 pm

1 stop9h 47m

Kelowna

Thu 10/1

5:25 am-2:43 pm

1 stop7h 18m

$424

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Mon 9/28

3:40 pm-11:27 pm

1 stop9h 47m

Kelowna

Thu 10/1

5:25 am-2:43 pm

1 stop7h 18m

$435

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 8/13

10:25 am-9:52 pm

1 stop13h 27m

Kelowna

Mon 8/17

10:50 pm-2:35 pm

1 stop13h 45m

$627

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 9/24

1:19 pm-10:05 pm

2 stops10h 46m

Kelowna

Mon 9/28

8:15 pm-11:55 am

2 stops13h 40m

$738

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 8/13

10:25 am-9:52 pm

1 stop13h 27m

Kelowna

Fri 8/21

11:45 am-9:40 am

1 stop19h 55m

$769

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 9/24

2:00 pm-11:50 pm

2 stops11h 50m

Kelowna

Mon 9/28

6:05 am-6:33 pm

2 stops10h 28m

$902

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.
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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
11,269 reviews
Search Air Canada flights
Alaska AirlinesPriceFrom $342Free CancellationRating
7.9
12,583 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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