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Cheap flights from Kelowna to Chicago from C$ 201

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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — CHI
4 Aug — 11 Aug1
1 adult

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 30 July 2025.

Round-trip from

C$ 316

One-way from

C$ 201

Popular in

March

Cheapest in

December

Average price

C$ 583
WestJet
  • WestJet
  • 16/10-18/10
  • 2 total stops
  • 15h 52m total
  • Kelowna to Chicago
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WestJet
  • WestJet
  • 3/9
  • 1 total stop
  • 8h 48m total
  • Kelowna to Chicago
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Highest demand for flights based on searches. 18% potential increase in price (C$ 178 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease (C$ 35 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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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 30 July 2025.

Thu 16/107:00 a.m.YLW - ORD
1 stop7h 43mWestJet
Sat 18/105:30 p.m.ORD - YLW
1 stop8h 09mWestJet
Deal found 30/7C$ 316
Fri 29/88:35 p.m.YLW - ORD
1 stop16h 19mAir Canada
Mon 1/97:41 p.m.ORD - YLW
1 stop15h 30mAir Canada
Deal found 28/7C$ 625
Fri 29/82:47 p.m.YLW - ORD
2 stops31h 12mAlaska Airlines
Mon 1/96:20 a.m.ORD - YLW
1 stop9h 37mAlaska Airlines
Deal found 28/7C$ 651
Fri 29/82:00 p.m.YLW - ORD
2 stops19h 43mMultiple Airlines
Mon 1/910:49 a.m.ORD - YLW
2 stops10h 35mMultiple Airlines
Deal found 28/7C$ 654
Thu 16/108:15 p.m.YLW - MDW
2 stops11h 25mWestJet
Sat 18/1010:35 a.m.MDW - YLW
2 stops15h 04mWestJet
Deal found 30/7C$ 964
Fri 29/87:45 p.m.YLW - MDW
2 stops13h 49mMultiple Airlines
Mon 1/910:45 a.m.MDW - YLW
1 stop13h 40mMultiple Airlines
Deal found 28/7C$ 1,156
Thu 18/95:55 a.m.YLW - MDW
2 stops10h 40mDelta
Sat 20/91:43 p.m.MDW - YLW
2 stops11h 47mDelta
Deal found 29/7C$ 2,763

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 30 July 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

Thu 16/10

7:00 a.m.-4:43 p.m.

1 stop7h 43m

Chicago O'Hare Intl

Sat 18/10

5:30 p.m.-11:39 p.m.

1 stop8h 09m

C$ 316

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 29/8

8:35 p.m.-2:54 p.m.

1 stop16h 19m

Chicago O'Hare Intl

Mon 1/9

7:41 p.m.-9:11 a.m.

1 stop15h 30m

C$ 625

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 29/8

2:47 p.m.-11:59 p.m.

2 stops31h 12m

Chicago O'Hare Intl

Mon 1/9

6:20 a.m.-1:57 p.m.

1 stop9h 37m

C$ 651

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 29/8

2:00 p.m.-11:43 a.m.

2 stops19h 43m

Chicago O'Hare Intl

Mon 1/9

10:49 a.m.-7:24 p.m.

2 stops10h 35m

C$ 654

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 16/10

8:15 p.m.-9:40 a.m.

2 stops11h 25m

Chicago Midway

Sat 18/10

10:35 a.m.-11:39 p.m.

2 stops15h 04m

C$ 964

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 29/8

7:45 p.m.-11:34 a.m.

2 stops13h 49m

Chicago Midway

Mon 1/9

10:45 a.m.-10:25 p.m.

1 stop13h 40m

C$ 1,156

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 18/9

5:55 a.m.-6:35 p.m.

2 stops10h 40m

Chicago Midway

Sat 20/9

1:43 p.m.-11:30 p.m.

2 stops11h 47m

C$ 2,763

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 3/9

5:55 a.m.-4:43 p.m.

1 stop8h 48m

C$ 201

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 12/9

8:45 p.m.-4:43 p.m.

2 stops17h 58m

C$ 247

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 12/9

8:45 p.m.-11:17 p.m.

2 stops24h 32m

C$ 276

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/7

Showing 1-10 of 13 results
1
2

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.

Calgary (YYC) – chosen by Cheapflights users on 25% 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$ 371.

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 Vancouver (YVR) have the shortest average one-way travel time for 1-stop routes: 7h 03m.

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 Seattle (SEA) offer the fastest connection on this route, with an average layover time of 2h 02m.

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 30 July 2025.
Read through reviews of airlines operating flights from Kelowna to Chicago, such as Alaska Airlines,Porter Airlines, andDelta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
Porter Airlines
8.0
Very good
318 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
Delta
8.0
Very good
7,980 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
United Airlines
7.4
Good
8,896 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
WestJet
7.2
Good
2,975 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave

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.

  • What are the cheapest airlines flying from Kelowna to Chicago round-trip?

    Cheapflights users have booked flights from Kelowna to Chicago round-trip from C$ 316. Other airlines that can offer you cheap pricing are Air Canada, from C$ 625, and Alaska Airlines, from C$ 651. WestJet is currently priced 45% 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$ 201 on WestJet. Other airlines that offer cheap prices include Air Canada from C$ 281 and United Airlines from C$ 332 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$ 352). 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

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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 30 July 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 371AverageC$ 508FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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

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

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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.

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