Find flights
When to book
Airlines
FAQs

Cheap flights from Kelowna to Chicago from C$ 153

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 19/1. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — CHI
15 Oct — 22 Oct1
1 adult
1 adult, Economy

Cheap 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 15 September 2025.

Round-trip from

C$ 373

One-way from

C$ 153

Popular in

March

Cheapest in

April

Average price

C$ 776
United Airlines
  • United Airlines
  • 16/12-7/1
  • 4 total stops
  • 28h 40m total
  • Kelowna to Chicago
Search Deals
WestJet
  • WestJet
  • 19/1
  • 1 total stop
  • 6h 15m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 109 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Kelowna to Chicago

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 15 September 2025.

Tue 16/1210:25 a.m.YLW - ORD
2 stops16h 35mUnited Airlines
Wed 7/18:45 a.m.ORD - YLW
1 stop6h 05mUnited Airlines
Deal found 14/9C$ 373
Tue 16/1210:25 a.m.YLW - ORD
2 stops16h 35mUnited Airlines
Sat 3/13:40 p.m.ORD - YLW
1 stop9h 18mUnited Airlines
Deal found 14/9C$ 448
Tue 16/125:35 p.m.YLW - ORD
1 stop28h 24mAlaska Airlines
Wed 7/17:45 a.m.ORD - YLW
1 stop6h 49mAlaska Airlines
Deal found 14/9C$ 484
Sun 21/1210:25 a.m.YLW - ORD
2 stops11h 34mUnited Airlines
Wed 7/13:40 p.m.ORD - YLW
1 stop9h 18mUnited Airlines
Deal found 14/9C$ 528
Fri 19/125:20 a.m.YLW - ORD
2 stops16h 39mUnited Airlines
Thu 8/11:00 p.m.ORD - YLW
1 stop9h 09mUnited Airlines
Deal found 14/9C$ 529
Wed 17/125:20 a.m.YLW - ORD
1 stop7h 21mUnited Airlines
Tue 6/18:45 a.m.ORD - YLW
1 stop6h 05mUnited Airlines
Deal found 14/9C$ 539
Thu 18/1210:25 a.m.YLW - ORD
2 stops11h 34mUnited Airlines
Thu 8/19:00 a.m.ORD - YLW
2 stops13h 09mUnited Airlines
Deal found 14/9C$ 546
Mon 22/125:20 a.m.YLW - ORD
1 stop12h 34mUnited Airlines
Mon 5/11:00 p.m.ORD - YLW
1 stop9h 09mUnited Airlines
Deal found 14/9C$ 547
Fri 19/128:55 p.m.YLW - ORD
1 stop15h 46mAir Canada
Mon 5/11:05 p.m.ORD - YLW
1 stop9h 04mAir Canada
Deal found 14/9C$ 551
Tue 16/1210:25 a.m.YLW - ORD
2 stops16h 35mUnited Airlines
Sun 4/13:40 p.m.ORD - YLW
1 stop9h 18mUnited Airlines
Deal found 14/9C$ 557
Mon 22/1210:25 a.m.YLW - ORD
2 stops11h 34mUnited Airlines
Tue 6/19:00 a.m.ORD - YLW
2 stops13h 09mUnited Airlines
Deal found 14/9C$ 576
Sat 20/127:55 p.m.YLW - MDW
2 stops14h 02mDelta
Tue 6/12:00 p.m.MDW - YLW
2 stops11h 55mDelta
Deal found 14/9C$ 1,405

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 15 September 2025.
Use the filters below to find and compare flights from Kelowna to Chicago that are best for you.

Fly from

Kelowna

Fly to

Chicago

Route

Depart

Return

Price

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 16/12

10:25 a.m.-5:00 a.m.

2 stops16h 35m

Chicago O'Hare Intl

Mon 5/1

7:05 a.m.-10:58 p.m.

2 stops17h 53m

C$ 373

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 16/12

10:25 a.m.-11:10 p.m.

2 stops10h 45m

Chicago O'Hare Intl

Tue 6/1

7:00 a.m.-10:58 p.m.

2 stops17h 58m

C$ 373

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 17/12

10:25 a.m.-11:59 p.m.

2 stops11h 34m

Chicago O'Hare Intl

Mon 5/1

7:05 a.m.-10:58 p.m.

2 stops17h 53m

C$ 373

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 17/12

10:25 a.m.-11:59 p.m.

2 stops11h 34m

Chicago O'Hare Intl

Sat 3/1

3:40 p.m.-10:58 p.m.

1 stop9h 18m

C$ 448

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sun 21/12

10:25 a.m.-11:59 p.m.

2 stops11h 34m

Chicago O'Hare Intl

Wed 7/1

12:53 p.m.-10:58 p.m.

2 stops12h 05m

C$ 528

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 19/12

5:20 a.m.-11:59 p.m.

2 stops16h 39m

Chicago O'Hare Intl

Mon 5/1

7:05 a.m.-10:58 p.m.

2 stops17h 53m

C$ 529

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sat 20/12

5:20 a.m.-11:59 p.m.

2 stops16h 39m

Chicago O'Hare Intl

Mon 5/1

7:05 a.m.-8:09 p.m.

2 stops15h 04m

C$ 529

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sat 20/12

5:20 a.m.-11:00 p.m.

2 stops15h 40m

Chicago O'Hare Intl

Wed 7/1

9:00 a.m.-8:09 p.m.

2 stops13h 09m

C$ 529

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sat 20/12

5:20 a.m.-11:00 p.m.

2 stops15h 40m

Chicago O'Hare Intl

Thu 8/1

9:00 a.m.-10:58 p.m.

2 stops15h 58m

C$ 529

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 19/12

5:20 a.m.-11:59 p.m.

2 stops16h 39m

Chicago O'Hare Intl

Wed 7/1

9:00 a.m.-8:09 p.m.

2 stops13h 09m

C$ 529

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/9

Showing 1-10 of 22 results
1
2
3

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

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.

Vancouver (YVR) – chosen by Cheapflights users on 27% 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 15 September 2025.
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
10,000 reviews
Check prices

Crew

7.8

Overall

7.1

Boarding

7.3

Entertainment

6.8

Comfort

7.1

Food

6.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Jun 2025

YVR - YWG

Should allow a carry- on baggage in economy class. The first 4 rows after first class should be allowed to use the closest bathroom.
Air Canada
7.1
Good
10,000 reviews
Air Canada
7.1
Good
10,000 reviews
Check prices

Crew

7.8

Overall

7.1

Boarding

7.3

Entertainment

6.8

Comfort

7.1

Food

6.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Jun 2025

YVR - YWG

Should allow a carry- on baggage in economy class. The first 4 rows after first class should be allowed to use the closest bathroom.

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 1 airline.

  • How long is the flight from Kelowna to Chicago?

    Departing from Kelowna to Chicago will take you 14h 02m. There are 2586 km between Kelowna and Chicago. Both multi-stop and direct flights can be found to your destination and back.

  • What is the cheapest airline to fly from Kelowna to Chicago round-trip?

    Cheapflights users have booked flights from Kelowna to Chicago round-trip from C$ 372. Air Canada is currently priced 37% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Kelowna to Chicago one-way?

    One-way options have recently been found by users for as low as C$ 153 on WestJet. Other airlines that offer cheap prices include Air Canada from C$ 170 and United Airlines from C$ 210 one-way.

  • 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.

  • What is the cheapest month to book a flight from Kelowna to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Kelowna to Chicago (average of C$ 261). Flying from Kelowna to Chicago in March is currently the most expensive (average of C$ 348). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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.

Top airline flying from Kelowna to Chicago

Discover the top airline that operate flights from Kelowna to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 15 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 372AverageC$ 545FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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.