Cheap flights from Chicago to Kelowna from $77

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 9/25. 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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Cheap round-trip flights

WestJet Logo
5:30 pm - 11:39 pmORD-YLW
8h 09m1 stop
WestJet Logo
7:00 am - 4:43 pmYLW-ORD
7h 43m1 stop
$180WestJet
Find Deal
Tue, Sep 30 - Sun, Oct 5
WestJet Logo
5:30 pm - 11:39 pmORD-YLW
8h 09m1 stop
WestJet Logo
7:00 am - 4:43 pmYLW-ORD
7h 43m1 stop
$196WestJet
Find Deal
Sat, Oct 11 - Sat, Oct 18
Air Canada Logo
3:40 pm - 10:58 pmORD-YLW
9h 18m1 stop
Air Canada Logo
5:20 am - 2:41 pmYLW-ORD
7h 21m1 stop
$223Air Canada
Find Deal
Wed, Oct 29 - Sun, Nov 2
WestJet Logo
5:30 pm - 9:22 amORD-YLW
17h 52m2 stops
WestJet Logo
7:00 am - 4:43 pmYLW-ORD
7h 43m1 stop
$227WestJet
Find Deal
Tue, Sep 30 - Sun, Oct 5
WestJet Logo
5:30 pm - 11:39 pmORD-YLW
8h 09m1 stop
WestJet Logo
2:20 pm - 4:43 pmYLW-ORD
24h 23m2 stops
$241WestJet
Find Deal
Sat, Oct 11 - Sat, Oct 18
 Logo
12:37 pm - 6:00 pmORD-YLW
31h 23m2 stops
 Logo
5:20 am - 1:35 pmYLW-ORD
6h 15m1 stop
Wed, Oct 29 - Sun, Nov 2
 Logo
5:01 am - 12:21 pmORD-YLW
9h 20m2 stops
 Logo
5:55 am - 4:51 pmYLW-ORD
8h 56m2 stops
Tue, Sep 30 - Sun, Oct 5
Alaska Airlines Logo
2:05 pm - 9:04 pmORD-YLW
8h 59m2 stops
Alaska Airlines Logo
1:20 pm - 1:04 pmYLW-ORD
21h 44m2 stops
$509Alaska Airlines
Find Deal
Wed, Jan 21 - Mon, Jan 26
Alaska Airlines Logo
2:05 pm - 9:04 pmORD-YLW
8h 59m2 stops
Alaska Airlines Logo
1:20 pm - 1:04 pmYLW-ORD
21h 44m2 stops
$538Alaska Airlines
Find Deal
Fri, Jan 9 - Sun, Jan 18
Delta Logo
2:00 pm - 11:55 pmMDW-YLW
11h 55m2 stops
Delta Logo
7:55 pm - 12:01 pmYLW-MDW
14h 06m2 stops
$857Delta
Find Deal
Wed, Jan 21 - Mon, Jan 26

WestJet flights from Chicago to Kelowna

Our best WestJet deals on Chicago to Kelowna flight tickets
WestJet
Sep 30
ORD5:30 pmChicago O'Hare Intl
8h 09m
1 stop
YLW11:39 pmKelowna
Oct 5
YLW7:00 amKelowna
7h 43m
1 stop
ORD4:43 pmChicago O'Hare Intl
WestJet
Oct 11
ORD5:30 pmChicago O'Hare Intl
8h 09m
1 stop
YLW11:39 pmKelowna
Oct 18
YLW7:00 amKelowna
7h 43m
1 stop
ORD4:43 pmChicago O'Hare Intl
WestJet
Sep 30
ORD5:30 pmChicago O'Hare Intl
17h 52m
2 stops
YLW9:22 amKelowna
Oct 5
YLW7:00 amKelowna
7h 43m
1 stop
ORD4:43 pmChicago O'Hare Intl

Air Canada flights from Chicago to Kelowna

Our best Air Canada deals on Chicago to Kelowna flight tickets
Air Canada
Oct 29
ORD3:40 pmChicago O'Hare Intl
9h 18m
1 stop
YLW10:58 pmKelowna
Nov 2
YLW5:20 amKelowna
7h 21m
1 stop
ORD2:41 pmChicago O'Hare Intl
Air Canada
Aug 31
ORD8:48 amChicago O'Hare Intl
12h 05m
1 stop
YLW6:53 pmKelowna
Sep 3
YLW5:55 amKelowna
7h 05m
1 stop
ORD3:00 pmChicago O'Hare Intl
Air Canada
Aug 31
ORD3:40 pmChicago O'Hare Intl
8h 53m
1 stop
YLW10:33 pmKelowna
Sep 3
YLW8:35 pmKelowna
18h 35m
2 stops
ORD5:10 pmChicago O'Hare Intl

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 28, 2025.
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

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 9/30

5:30 pm-11:39 pm

1 stop8h 09m

Kelowna

Sun 10/5

7:00 am-4:43 pm

1 stop7h 43m

$180

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sat 10/11

5:30 pm-11:39 pm

1 stop8h 09m

Kelowna

Sat 10/18

7:00 am-4:43 pm

1 stop7h 43m

$196

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Wed 10/29

3:40 pm-10:58 pm

1 stop9h 18m

Kelowna

Sun 11/2

5:20 am-2:41 pm

1 stop7h 21m

$223

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 9/30

5:30 pm-9:22 am

2 stops17h 52m

Kelowna

Sun 10/5

7:00 am-4:43 pm

1 stop7h 43m

$227

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sat 10/11

5:30 pm-11:39 pm

1 stop8h 09m

Kelowna

Sat 10/18

2:20 pm-4:43 pm

2 stops24h 23m

$241

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Wed 10/29

12:37 pm-6:00 pm

2 stops31h 23m

Kelowna

Sun 11/2

5:20 am-1:35 pm

1 stop6h 15m

$262

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 9/30

5:01 am-12:21 pm

2 stops9h 20m

Kelowna

Sun 10/5

5:55 am-4:51 pm

2 stops8h 56m

$334

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Wed 1/21

2:05 pm-9:04 pm

2 stops8h 59m

Kelowna

Mon 1/26

1:20 pm-1:04 pm

2 stops21h 44m

$509

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Fri 1/9

2:05 pm-9:04 pm

2 stops8h 59m

Kelowna

Sun 1/18

1:20 pm-1:04 pm

2 stops21h 44m

$538

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Wed 1/21

2:00 pm-11:55 pm

2 stops11h 55m

Kelowna

Mon 1/26

7:55 pm-12:01 pm

2 stops14h 06m

$857

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 day to depart on your flight to Kelowna?

On average, the least expensive day to fly to Kelowna from Chicago is on a Friday. momondo users have found tickets for Friday departures for as low as $429. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Wednesday as prices are generally higher than usual. According to our data, the average ticket price to Kelowna on Wednesday is $559.

What is the cheapest time of day to depart on your flight to Kelowna?

Our most recent data shows that the best time of day to fly to Kelowna is in the evening. Flights from Chicago to Kelowna during this time can be as low as $169. Try not to purchase tickets in the morning because they tend to be around $650. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

Direct flights

None
There are no direct flights from Chicago to Kelowna. There are no popular flight routes 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 8h 09m 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.

  • What is the most popular airline from Chicago to Kelowna?

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 $386Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
Alaska AirlinesPriceFrom $408Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $437Free CancellationRating
7.4
8,944 reviews
Search United Airlines flights

Traveling to a place near Kelowna?

Book flights to Kelowna if you plan to visit one of these locations
Revelstoke
Vernon
West Kelowna
Salmon Arm
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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1 adult
Tue 9/2
Tue 9/9

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