Find flights
When to book
Airlines
FAQs

Cheap flights from Kelowna to Chicago from C$ 203

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 22/5. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — CHI
10 May — 17 May1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Kelowna to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Kelowna to Chicago
Explore the most affordable flight options available from Kelowna to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 10 April 2026.

Fri 22/56:05 a.m.
YLW
-
ORD
1 stop8h 35m
WestJet
Sun 24/55:30 p.m.
ORD
-
YLW
1 stop6h 35m
WestJet
Deal found 8/4C$ 358
Sat 25/44:00 p.m.
YLW
-
ORD
1 stop22h 40m
WestJet
Sun 3/55:30 p.m.
ORD
-
YLW
1 stop6h 35m
WestJet
Deal found 7/4C$ 418
Wed 22/49:25 a.m.
YLW
-
ORD
1 stop8h 50m
Air Canada
Wed 29/48:50 a.m.
ORD
-
YLW
1 stop12h 42m
Air Canada
Deal found 5/4C$ 476
Wed 22/410:25 a.m.
YLW
-
ORD
1 stop7h 50m
United Airlines
Wed 29/47:00 a.m.
ORD
-
YLW
2 stops14h 32m
United Airlines
Deal found 5/4C$ 484
Sat 25/48:00 p.m.
YLW
-
ORD
2 stops12h 23m
Multiple Airlines
Sun 3/55:30 p.m.
ORD
-
YLW
1 stop6h 35m
Multiple Airlines
Deal found 6/4C$ 494
Sat 25/49:25 a.m.
YLW
-
ORD
1 stop8h 50m
Air Canada
Tue 28/48:50 a.m.
ORD
-
YLW
1 stop12h 42m
Air Canada
Deal found 5/4C$ 502
Fri 24/46:20 a.m.
YLW
-
ORD
2 stops16h 04m
Multiple Airlines
Sun 3/55:30 p.m.
ORD
-
YLW
1 stop6h 35m
Multiple Airlines
Deal found 6/4C$ 513
Sat 25/48:00 p.m.
YLW
-
MDW
2 stops14h 07m
Delta
Sun 3/51:24 p.m.
MDW
-
YLW
2 stops10h 41m
Delta
Deal found 7/4C$ 848
Fri 24/47:55 p.m.
YLW
-
MDW
2 stops14h 15m
Multiple Airlines
Sat 2/510:30 a.m.
MDW
-
YLW
1 stop26h 17m
Multiple Airlines
Deal found 6/4C$ 870
Wed 6/510:55 a.m.
YLW
-
MDW
3 stops19h 48m
WestJet
Fri 8/57:13 p.m.
MDW
-
YLW
3 stops24h 47m
WestJet
Deal found 6/4C$ 920
Fri 24/411:40 p.m.
YLW
-
MDW
1 stop10h 30m
Multiple Airlines
Sun 3/53:20 p.m.
MDW
-
YLW
2 stops17h 40m
Multiple Airlines
Deal found 6/4C$ 1,050
Fri 24/46:35 p.m.
YLW
-
MDW
2 stops13h 21m
WestJet
Sun 3/59:27 a.m.
MDW
-
YLW
2 stops14h 38m
WestJet
Deal found 7/4C$ 1,067

Find flight deals from Kelowna to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Kelowna (YLW) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 10 April 2026.

Round-trip from

C$ 358

One-way from

C$ 203

Popular in

July

Cheapest in

May

Average price

C$ 589
WestJet
  • WestJet
  • 22/5-24/5
  • 2 total stops
  • 15h 10m total
  • Kelowna to Chicago
Search Deals
WestJet
  • WestJet
  • 22/5
  • 1 total stop
  • 6h 50m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 142 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 42 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kelowna to Chicago 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, Cheapflights users made 629,999 searches. Data last updated 10 April 2026.
Use the filters below to find and compare flights from Kelowna to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 22/4

10:25 a.m.-8:15 p.m.

1 stop7h 50m

Chicago O'Hare Intl

Wed 29/4

7:00 a.m.-7:32 p.m.

2 stops14h 32m

C$ 484

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 22/4

10:25 a.m.-12:30 a.m.

2 stops12h 05m

Chicago O'Hare Intl

Wed 29/4

8:50 a.m.-7:32 p.m.

1 stop12h 42m

C$ 497

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sat 23/5

7:50 a.m.-9:50 p.m.

2 stops12h 00m

Chicago O'Hare Intl

Sat 30/5

11:09 a.m.-10:05 p.m.

2 stops12h 56m

C$ 522

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 5/5

6:05 p.m.-6:20 a.m.

2 stops10h 15m

Chicago O'Hare Intl

Wed 6/5

8:35 p.m.-11:00 a.m.

1 stop16h 25m

C$ 596
Quickest round-trip

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 1/7

8:30 p.m.-5:40 a.m.

1 stop7h 10m

Chicago O'Hare Intl

Wed 8/7

5:00 a.m.-1:14 p.m.

2 stops10h 14m

C$ 603

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 29/7

11:00 p.m.-9:00 a.m.

1 stop8h 00m

Chicago O'Hare Intl

Wed 26/8

5:00 a.m.-1:14 p.m.

2 stops10h 14m

C$ 606

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sat 25/4

5:20 a.m.-6:59 p.m.

2 stops11h 39m

Chicago O'Hare Intl

Sun 3/5

7:00 a.m.-11:13 p.m.

2 stops18h 13m

C$ 614

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 5/5

2:50 p.m.-5:40 a.m.

2 stops12h 50m

Chicago O'Hare Intl

Wed 6/5

8:35 p.m.-6:53 p.m.

2 stops24h 18m

C$ 628

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sat 25/4

5:20 a.m.-12:29 a.m.

2 stops17h 09m

Chicago O'Hare Intl

Tue 28/4

7:00 a.m.-7:32 p.m.

2 stops14h 32m

C$ 636

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sat 25/4

8:00 p.m.-12:07 p.m.

2 stops14h 07m

Chicago Midway

Sun 3/5

1:24 p.m.-10:05 p.m.

2 stops10h 41m

C$ 848

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/4

Showing 1-10 of 39 resultsSorted by cheapest first
1
2
3
4

Best time to book a flight from Kelowna to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Kelowna with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Kelowna to Chicago

How much does it cost to fly round-trip from Kelowna to Chicago?

What’s the top layover airport for flights from Kelowna to Chicago?

Share of one-stop round-trip flights from Kelowna to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Calgary (YYC) – chosen by Cheapflights users on 44% of one-stop itineraries from Kelowna to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Kelowna to Chicago?

Average round-trip fare for 1-stop flights from Kelowna to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Toronto (YYZ) is the most affordable 1-stop option, with an average round-trip price of C$ 372.

What’s the fastest layover option from Kelowna to Chicago?

Shortest average travel time for 1-stop one-way flights from Kelowna to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Calgary (YYC) have the shortest average one-way travel time for 1-stop routes: 6h 44m.

Which airport typically offers the quickest layover for flights from Kelowna to Chicago?

Average layover duration for 1-stop one-way flights from Kelowna to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Calgary (YYC) offer the fastest connection on this route, with an average layover time of 1h 46m.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 10 April 2026.
Read through reviews of airlines operating flights from Kelowna to Chicago, such as Air Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
10,915 reviews
Check prices

Crew

7.8

Entertainment

6.8

Comfort

7.1

Boarding

7.3

Overall

7.1

Food

6.3

Reviews

1 / 20
6.0
Good

Paula,Mar 2026

YVR - PSP

Everything was OK, but we waited on the tarmac for an hour and 20 minutes after landing because there was no available gate. This is a daily occurrence at the Palm Springs airport, and happens with Air Canada and WestJet constantly.
Air Canada
7.1
Good
10,915 reviews
Air Canada
7.1
Good
10,915 reviews
Check prices

Crew

7.8

Entertainment

6.8

Comfort

7.1

Boarding

7.3

Overall

7.1

Food

6.3

Reviews

1 / 20
6.0
Good

Paula,Mar 2026

YVR - PSP

Everything was OK, but we waited on the tarmac for an hour and 20 minutes after landing because there was no available gate. This is a daily occurrence at the Palm Springs airport, and happens with Air Canada and WestJet constantly.

Related info for your journey

Find useful and relevant information for your journey from Kelowna to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Kelowna to Chicago?

    Located just 11.2 km from the city centre, Kelowna is the airport most travellers will use when flying to Chicago from Kelowna. Booking flights from Kelowna (YLW) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 0 different airlines.

  • How long is the flight from Kelowna to Chicago?

    Departing from Kelowna to Chicago will take you 7h 50m. There are 2565 km between Kelowna and Chicago. Both multi-stop and direct flights can be found to your destination and back.

  • Can I find deals for flights from Kelowna to Chicago that include hotel bookings?

    Yes. In addition to deals on Kelowna to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kelowna to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kelowna to Chicago.

  • Can I find deals for business class flights from Kelowna to Chicago?

    Yes. Cheapflights offers flight deals from Kelowna to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Kelowna to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Kelowna to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Kelowna to Chicago?

Cheapflights simply makes it quick and affordable to book flights from Kelowna to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Kelowna to Chicago with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Kelowna to Chicago flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Kelowna to Chicago become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.