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Flight Deals from Chicago to Kelowna from $192

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Bundle + Save

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Save an average of $240 per person when bundling your flight and hotel together with Priceline

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Stops

  • Up to 1 stop
    $471
  • Up to 3 stops
    $826
  • Up to 2 stops
    $508

Airlines

  • Air Canada
    $471
  • Alaska Airlines
    $630
  • Delta Air Lines
    $627
  • Porter Airlines
    $880
  • United Airlines
    $522
  • WestJet
    $871

Cabin Class

  • Economy
    $471

Departure Airports

  • Chicago Metropolitan Area
    $508
  • Chicago O Hare Airport
    $471

Arrival Airports

  • Kelowna International Airport
    $471

Layover Airports

  • Calgary International Airport
    $627
  • Chicago O Hare Airport
    $508
  • Kelowna International Airport
    $508
  • Seattle Tacoma International Airport
    $630
  • Toronto Pearson Airport
    $471
  • Vancouver International Airport
    $730

Best Price. GUARANTEED.

Exclusively for Priceline Members
Tired of searching? Book now!
We'll refund the difference if you find a lower price.

Air Canada Logo
Air Canada

06/06/26

ORD
14h 56m
YYZ

06/06/26

YLW
Air Canada Logo
Air Canada

06/15/26

YLW
7h 10m
YYZ

06/16/26

ORD
$471
Air Canada Logo
Air Canada

06/06/26

CHI
6h 6m
YYZ
YLW

06/06/26

YLW
Air Canada Logo
Air Canada

06/12/26

YLW
10h 10m
YYZ
ORD

06/13/26

CHI
$508
United Airlines Logo
United Airlines

06/06/26

ORD
16h 42m
YYZ

06/06/26

YLW
United Airlines Logo
United Airlines

06/12/26

YLW
8h 10m
YYZ

06/13/26

ORD
$522
Bundle + Save
Book a flight & hotel together for extra savings.
On average save $240 per traveler
United Airlines Logo
United Airlines

06/06/26

CHI
14h 42m
YYZ
YLW

06/06/26

YLW
United Airlines Logo
United Airlines

06/12/26

YLW
10h 10m
YYZ
ORD

06/13/26

CHI
$522
Delta Air Lines Logo
Delta Air Lines

09/01/26

ORD
6h 35m
YYC

09/01/26

YLW
Delta Air Lines Logo
Delta Air Lines

09/03/26

YLW
6h 50m
YYC

09/03/26

ORD
$627
Alaska Airlines Logo
Alaska Airlines

06/06/26

CHI
7h 6m
SEA
YLW

06/06/26

YLW
Alaska Airlines Logo
Alaska Airlines

06/12/26

YLW
10h 13m
SEA
ORD

06/12/26

CHI
$630
Air Canada Logo
Air Canada

06/01/26

CHI
11h 51m
YYZ
YLW

06/01/26

YLW
Air Canada Logo
Air Canada

06/06/26

YLW
10h 10m
YYZ
ORD

06/07/26

CHI
$719
United Airlines Logo
United Airlines

05/29/26

CHI
10h 13m
YYC
YLW

05/29/26

YLW
United Airlines Logo
United Airlines

05/29/26

YLW
9h 10m
YVR
ORD

05/30/26

CHI
$730
United Airlines Logo
United Airlines

06/01/26

CHI
5h 28m
YVR
YLW

06/01/26

YLW
United Airlines Logo
United Airlines

06/06/26

YLW
9h 10m
YVR
ORD

06/07/26

CHI
$764
United Airlines Logo
United Airlines

06/21/26

CHI
9h 5m
YYZ
YLW

06/21/26

YLW
United Airlines Logo
United Airlines

06/28/26

YLW
9h 10m
YVR
ORD

06/29/26

CHI
$773
Alaska Airlines Logo
Alaska Airlines

06/01/26

CHI
7h 6m
SEA
YLW

06/01/26

YLW
Alaska Airlines Logo
Alaska Airlines

06/09/26

YLW
14h 24m
SEA
ORD

06/10/26

CHI
$793
Air Canada Logo
Air Canada

06/06/26

CHI
9h 13m
YYZ
YVR
YLW

06/06/26

YLW
Air Canada Logo
Air Canada

06/12/26

YLW
10h 10m
YYZ
ORD

06/13/26

CHI
$826
WestJet Logo
WestJet

06/06/26

CHI
4h 35m
YYC
YLW

06/06/26

YLW
WestJet Logo
WestJet

06/12/26

YLW
10h 13m
SEA
ORD

06/12/26

CHI
$871
Bundle + Save
Book a flight & hotel together for extra savings.
On average save $240 per traveler
Air Canada Logo
Air Canada

05/29/26

CHI
10h 13m
YYC
YLW

05/29/26

YLW
Air Canada Logo
Air Canada

05/29/26

YLW
9h 10m
YVR
ORD

05/30/26

CHI
$872
Porter Airlines Logo
Porter Airlines

07/10/26

ORD
10h 13m
YYZ

07/10/26

YLW
Porter Airlines Logo
Porter Airlines

07/13/26

YLW
10h 54m
YYZ

07/14/26

ORD
$880
United Airlines Logo
United Airlines

06/06/26

CHI
9h 13m
YYZ
YVR
YLW

06/06/26

YLW
United Airlines Logo
United Airlines

06/12/26

YLW
10h 10m
YYZ
ORD

06/13/26

CHI
$978
Alaska Airlines Logo
Alaska Airlines

05/29/26

CHI
4h 46m
SEA
YLW

05/29/26

YLW
Alaska Airlines Logo
Alaska Airlines

05/31/26

YLW
14h 44m
SEA
ORD

06/01/26

CHI
$980
WestJet Logo
WestJet

06/01/26

CHI
4h 35m
YYC
YLW

06/01/26

YLW
WestJet Logo
WestJet

06/06/26

YLW
14h 44m
SEA
ORD

06/07/26

CHI
$1013
Air Canada Logo
Air Canada

05/29/26

CHI
10h 19m
YYZ
YVR
YLW

05/29/26

YLW
Air Canada Logo
Air Canada

05/29/26

YLW
9h 10m
YVR
ORD

05/30/26

CHI
$1019
WestJet Logo
WestJet

05/29/26

CHI
4h 35m
YYC
YLW

05/29/26

YLW
WestJet Logo
WestJet

05/31/26

YLW
20h 25m
YYC
ORD

06/01/26

CHI
$1042
Air Canada Logo
Air Canada

06/01/26

CHI
9h 58m
YYZ
YVR
YLW

06/01/26

YLW
Air Canada Logo
Air Canada

06/06/26

YLW
9h 10m
YVR
ORD

06/07/26

CHI
$1172

Top Deals on flights from Chicago to Kelowna

Chicago, US (CHI) - Kelowna, CA (YLW)

WestJet Logo
WestJet

Jun 2

ORD
7h 35m
YYC

Jun 2

YLW

as low as

$192

Chicago, US (CHI) - Kelowna, CA (YLW)

Alaska Airlines Logo
Alaska Airlines

Jun 13

CHI
6h 56m
SEA
YLW

Jun 13

YLW

as low as

$219

Chicago, US (CHI) - Kelowna, CA (YLW)

Alaska Airlines Logo
Alaska Airlines

Jun 13

ORD
8h 56m
SEA

Jun 13

YLW

as low as

$219

Chicago, US (CHI) - Kelowna, CA (YLW)

United Airlines Logo
United Airlines

Jun 13

ORD
16h 44m
YVR

Jun 14

YLW

as low as

$222

Chicago, US (CHI) - Kelowna, CA (YLW)

United Airlines Logo
United Airlines

May 30

CHI
14h 3m
YVR
YLW

May 31

YLW

as low as

$239

Chicago, US (CHI) - Kelowna, CA (YLW)

WestJet Logo
WestJet

Jun 2

CHI
4h 35m
YYC
YLW

Jun 2

YLW

as low as

$264

Chicago, US (CHI) - Kelowna, CA (YLW)

United Airlines Logo
United Airlines

Jun 15

CHI
14h 44m
YVR
YLW

Jun 16

YLW

as low as

$309

Chicago, US (CHI) - Kelowna, CA (YLW)

Alaska Airlines Logo
Alaska Airlines

Jun 8

CHI
7h 6m
SEA
YLW

Jun 8

YLW

as low as

$317

Chicago, US (CHI) - Kelowna, CA (YLW)

United Airlines Logo
United Airlines

Jun 6

CHI
14h 42m
YYZ
YLW

Jun 6

YLW

as low as

$338

Chicago, US (CHI) - Kelowna, CA (YLW)

Air Canada Logo
Air Canada

May 30

CHI
14h 3m
YVR
YLW

May 31

YLW

as low as

$347

Chicago, US (CHI) - Kelowna, CA (YLW)

Air Canada Logo
Air Canada

Jun 12

CHI
11h 8m
YYZ
YLW

Jun 12

YLW

as low as

$349

Chicago, US (CHI) - Kelowna, CA (YLW)

United Airlines Logo
United Airlines

Jun 12

CHI
13h 1m
YYZ
YLW

Jun 12

YLW

as low as

$349

Good to Know

Essential information to help you plan your flight from Chicago to Kelowna

Cheapest Flight

$192

The lowest price we found in the last two weeks, departing Jun 2 and returning Jun 2

Airline WS1 stop ‧ 7h 35m ‧ economy

Fastest Flights

$871

The fastest flight that we found in the last two weeks, departing Jun 6 and returning Jun 12

Airline WS2 stops ‧ 4h 35m ‧ economy

Cheapest Flight Round-trip

$471

Cheapest price found in the last 14 days, departing Jun 6 and returning Jun 16

Airline AC1 stop ‧ 14h 56m ‧ economy

Cheapest Flight One-way

$192

Cheapest price found in the last 14 days, departing Jun 2

Airline WS1 stop ‧ 7h 35m ‧ economy

Cheapest Layover airport

$192

The cheapest layover airport to Kelowna is currently $192

Airline WS1 stop ‧ 7h 35m ‧ economy

Best Arrival airport

$192

The best arrival airport to Kelowna is currently $192

Airline WS1 stop ‧ 7h 35m ‧ economy

Best Departure airport

$192

The best departure airport to Kelowna is currently $192

Airline WS1 stop ‧ 7h 35m ‧ economy

Cheapest Airline

$192

The cheapest airline to Kelowna is currently $192

Airline WS1 stop ‧ 7h 35m ‧ economy

Flights to Kelowna