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Cheap flights from Chicago to Kelowna from $148

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 10/29. 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.
Air Canada Logo
3:40 pm - 11:12 pm
ORD
-
YLW
9h 32m
1 stop
Air Canada Logo
5:25 am - 2:48 pm
YLW
-
ORD
7h 23m
1 stop
$428Air Canada
Tue, Oct 20 - Sat, Oct 24
Air Canada Logo
8:45 am - 6:55 pm
ORD
-
YLW
12h 10m
2 stops
Air Canada Logo
5:25 am - 2:48 pm
YLW
-
ORD
7h 23m
1 stop
$437Air Canada
Tue, Oct 20 - Sat, Oct 24
Air Canada Logo
8:45 am - 6:55 pm
ORD
-
YLW
12h 10m
2 stops
Air Canada Logo
5:25 am - 7:48 pm
YLW
-
ORD
12h 23m
2 stops
$450Air Canada
Tue, Oct 20 - Sat, Oct 24
WestJet Logo
5:30 pm - 9:45 am
ORD
-
YLW
18h 15m
2 stops
WestJet Logo
8:45 pm - 4:40 pm
YLW
-
ORD
17h 55m
2 stops
$458WestJet
Tue, Aug 11 - Sun, Aug 16
WestJet Logo
5:30 pm - 8:20 am
ORD
-
YLW
16h 50m
1 stop
WestJet Logo
8:45 pm - 4:40 pm
YLW
-
ORD
17h 55m
2 stops
$461WestJet
Tue, Aug 11 - Sun, Aug 16
Multiple Airlines Logo
6:00 am - 12:56 pm
ORD
-
YLW
8h 56m
1 stop
Multiple Airlines Logo
7:50 am - 4:40 pm
YLW
-
ORD
6h 50m
1 stop
$467Multiple Airlines
Thu, Aug 13 - Mon, Aug 17
Multiple Airlines Logo
6:00 am - 12:56 pm
ORD
-
YLW
8h 56m
1 stop
Multiple Airlines Logo
6:05 am - 4:40 pm
YLW
-
ORD
8h 35m
1 stop
$472Multiple Airlines
Tue, Jul 14 - Tue, Jul 21
Porter Airlines Logo
3:20 pm - 10:47 am
MDW
-
YLW
21h 27m
1 stop
Porter Airlines Logo
11:45 am - 9:40 am
YLW
-
MDW
19h 55m
1 stop
$705Porter Airlines
Tue, Jul 14 - Tue, Jul 21
Porter Airlines Logo
10:15 am - 11:55 am
MDW
-
YLW
27h 40m
2 stops
Porter Airlines Logo
12:50 pm - 9:35 am
YLW
-
MDW
18h 45m
2 stops
$896Porter Airlines
Mon, Jun 1 - Wed, Jun 10
Delta Logo
1:27 pm - 10:05 pm
MDW
-
YLW
10h 38m
2 stops
Delta Logo
6:05 am - 6:33 pm
YLW
-
MDW
10h 28m
2 stops
$1,087Delta
Tue, Aug 11 - Sun, Aug 16

Porter Airlines flights from Chicago to Kelowna

Our best Porter Airlines deals on Chicago to Kelowna flight tickets
Porter Airlines
Jul 14
MDW3:20 pmChicago Midway
21h 27m
1 stop
YLW10:47 amKelowna
Jul 21
YLW11:45 amKelowna
19h 55m
1 stop
MDW9:40 amChicago Midway
$705
Porter Airlines
Jun 1
MDW10:15 amChicago Midway
27h 40m
2 stops
YLW11:55 amKelowna
Jun 10
YLW12:50 pmKelowna
18h 45m
2 stops
MDW9:35 amChicago Midway
$896
Porter Airlines
Jul 14
MDW10:25 amChicago Midway
27h 30m
2 stops
YLW11:55 amKelowna
Jul 21
YLW12:50 pmKelowna
18h 50m
2 stops
MDW9:40 amChicago Midway
$902

United Airlines flights from Chicago to Kelowna

Our best United Airlines deals on Chicago to Kelowna flight tickets
United Airlines
May 25
ORD5:00 amChicago O'Hare Intl
9h 18m
2 stops
YLW12:18 pmKelowna
May 28
YLW8:30 pmKelowna
7h 10m
1 stop
ORD5:40 amChicago O'Hare Intl
$588
United Airlines
May 25
ORD5:00 amChicago O'Hare Intl
9h 18m
2 stops
YLW12:18 pmKelowna
May 28
YLW6:05 pmKelowna
11h 11m
2 stops
ORD7:16 amChicago O'Hare Intl
$604
United Airlines
Jul 14
ORD5:00 amChicago O'Hare Intl
9h 19m
2 stops
YLW12:19 pmKelowna
Jul 21
YLW7:25 pmKelowna
8h 15m
1 stop
ORD5:40 amChicago O'Hare Intl
$610

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 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

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 10/20

3:40 pm-11:12 pm

1 stop9h 32m

Kelowna

Sat 10/24

5:25 am-2:48 pm

1 stop7h 23m

$428

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 10/20

8:45 am-6:55 pm

2 stops12h 10m

Kelowna

Sat 10/24

5:25 am-2:48 pm

1 stop7h 23m

$437

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 10/20

8:45 am-6:55 pm

2 stops12h 10m

Kelowna

Sat 10/24

5:25 am-7:48 pm

2 stops12h 23m

$450

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 8/11

5:30 pm-9:45 am

2 stops18h 15m

Kelowna

Sun 8/16

8:45 pm-4:40 pm

2 stops17h 55m

$458

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 8/11

5:30 pm-8:20 am

1 stop16h 50m

Kelowna

Sun 8/16

8:45 pm-4:40 pm

2 stops17h 55m

$461
Quickest round-trip

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Thu 8/13

6:00 am-12:56 pm

1 stop8h 56m

Kelowna

Mon 8/17

7:50 am-4:40 pm

1 stop6h 50m

$467

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Tue 7/14

6:00 am-12:56 pm

1 stop8h 56m

Kelowna

Tue 7/21

6:05 am-4:40 pm

1 stop8h 35m

$472

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 7/14

3:20 pm-10:47 am

1 stop21h 27m

Kelowna

Tue 7/21

11:45 am-9:40 am

1 stop19h 55m

$705

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 6/1

10:15 am-11:55 am

2 stops27h 40m

Kelowna

Wed 6/10

12:50 pm-9:35 am

2 stops18h 45m

$896

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 8/11

1:27 pm-10:05 pm

2 stops10h 38m

Kelowna

Sun 8/16

6:05 am-6:33 pm

2 stops10h 28m

$1,087

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
11,044 reviews
Search Air Canada flights
Alaska AirlinesPriceFrom $342Free CancellationRating
7.9
12,368 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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