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Flight Deals from Kelowna to Chicago from $178

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Bundle + Save

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Stops

  • Up to 1 stop
    $288
  • Up to 2 stops
    $288
  • Up to 3 stops
    $454

Airlines

  • WestJet
    $288

Cabin Class

  • Economy
    $288

Departure Airports

  • Kelowna International Airport
    $288

Arrival Airports

  • Chicago Metropolitan Area
    $288
  • Chicago O Hare Airport
    $288

Layover Airports

  • Calgary International Airport
    $288
  • Chicago O Hare Airport
    $288
  • Kelowna International Airport
    $288
  • Vancouver International Airport
    $454

Best Price. GUARANTEED.

Exclusively for Priceline Members
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WestJet Logo
WestJet

05/21/26

YLW
5h 50m
YYC

05/21/26

ORD
WestJet Logo
WestJet

05/29/26

ORD
7h 35m
YYC

05/29/26

YLW
$288
WestJet Logo
WestJet

05/21/26

YLW
8h 50m
YYC
ORD

05/21/26

CHI
WestJet Logo
WestJet

05/29/26

CHI
4h 35m
YYC
YLW

05/29/26

YLW
$288
WestJet Logo
WestJet

06/02/26

YLW
8h 50m
YYC
ORD

06/02/26

CHI
WestJet Logo
WestJet

06/10/26

CHI
4h 35m
YYC
YLW

06/10/26

YLW
$316
Bundle + Save
Book a flight & hotel together for extra savings.
On average save $240 per traveler
WestJet Logo
WestJet

06/02/26

YLW
8h 50m
YYC
ORD

06/02/26

CHI
WestJet Logo
WestJet

06/10/26

CHI
16h 15m
YYC
YVR
YLW

06/11/26

YLW
$454
WestJet Logo
WestJet

05/15/26

YLW
8h 50m
YYC
ORD

05/15/26

CHI
WestJet Logo
WestJet

05/19/26

CHI
4h 35m
YYC
YLW

05/19/26

YLW
$1303

Top Deals on flights from Kelowna to Chicago

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

WestJet Logo
WestJet

Jun 3

YLW
5h 50m
YYC

Jun 3

ORD

as low as

$178

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

 Logo

Jun 3

YLW
6h 10m
YVR

Jun 4

ORD

as low as

$209

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

 Logo

Jun 7

YLW
14h 44m
SEA
ORD

Jun 8

CHI

as low as

$341

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

 Logo

Jun 7

YLW
10h 10m
YYZ
ORD

Jun 8

CHI

as low as

$347

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

 Logo

Aug 17

YLW
10h 49m
YYZ

Aug 18

ORD

as low as

$355

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

 Logo

Jun 18

YLW
10h 13m
SEA
ORD

Jun 18

CHI

as low as

$400

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

WestJet Logo
WestJet

Jun 7

YLW
22h 10m
YYC
ORD

Jun 8

CHI

as low as

$424

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

WestJet Logo
WestJet

Jun 7

YLW
22h 5m
YVR
YYC
ORD

Jun 8

CHI

as low as

$472

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

WestJet Logo
WestJet

Jun 18

YLW
13h 58m
YYC
ATL
ORD

Jun 19

CHI

as low as

$555

Good to Know

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

Cheapest Flight

$178

The lowest price we found in the last two weeks, departing Jun 3 and returning Jun 3

Airline WS1 stop ‧ 5h 50m ‧ economy

Fastest Flights

$288

The fastest flight that we found in the last two weeks, departing May 21 and returning May 29

Airline WS1 stop ‧ 5h 50m ‧ economy

Cheapest Flight Round-trip

$288

Cheapest price found in the last 14 days, departing May 21 and returning May 29

Airline WS1 stop ‧ 5h 50m ‧ economy

Cheapest Flight One-way

$178

Cheapest price found in the last 14 days, departing Jun 3

Airline WS1 stop ‧ 5h 50m ‧ economy

Cheapest Layover airport

$288

The cheapest layover airport to Chicago is currently $288

Airline WS2 stops ‧ 8h 50m ‧ economy

Best Arrival airport

$178

The best arrival airport to Chicago is currently $178

Airline WS1 stop ‧ 5h 50m ‧ economy

Best Departure airport

$178

The best departure airport to Chicago is currently $178

Airline WS1 stop ‧ 5h 50m ‧ economy

Cheapest Airline

$178

The cheapest airline to Chicago is currently $178

Airline WS1 stop ‧ 5h 50m ‧ economy