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Cheap flights from Kelowna to Chicago from C$ 332

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — CHI
31 Mar — 7 Apr1
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 26 March 2025.

Round-trip from

C$ 332

Popular in

March

Cheapest in

August

Average price

C$ 882
Air Canada
  • Air Canada
  • 9/6-14/6
  • 2 total stops
  • 16h 34m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 26 March 2025.

Mon 9/67:30 p.m.YLW - ORD
1 stop8h 08mAir Canada
Sat 14/64:00 p.m.ORD - YLW
1 stop8h 26mAir Canada
Deal found 26/3C$ 332
Fri 9/512:15 p.m.YLW - ORD
1 stop26h 29mWestJet
Fri 16/55:30 p.m.ORD - YLW
1 stop8h 19mWestJet
Deal found 25/3C$ 386
Fri 30/55:45 a.m.YLW - ORD
1 stop6h 58mUnited Airlines
Mon 2/65:02 a.m.ORD - YLW
2 stops19h 30mUnited Airlines
Deal found 25/3C$ 398
Fri 9/55:55 a.m.YLW - ORD
2 stops10h 42mDelta
Fri 16/55:30 p.m.ORD - YLW
1 stop8h 19mDelta
Deal found 25/3C$ 493
Thu 24/411:10 a.m.YLW - ORD
2 stops11h 25mMultiple Airlines
Thu 1/58:25 p.m.ORD - YLW
2 stops24h 30mMultiple Airlines
Deal found 25/3C$ 528
Fri 9/55:55 a.m.YLW - MDW
2 stops10h 50mDelta
Fri 16/51:08 p.m.MDW - YLW
2 stops12h 41mDelta
Deal found 25/3C$ 548
Thu 15/53:25 p.m.YLW - ORD
1 stop30h 34mAlaska Airlines
Mon 19/56:00 a.m.ORD - YLW
1 stop10h 35mAlaska Airlines
Deal found 25/3C$ 659
Sun 29/67:00 a.m.YLW - MDW
2 stops8h 45mWestJet
Sat 5/79:21 a.m.MDW - YLW
2 stops8h 03mWestJet
Deal found 25/3C$ 1,030

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 26 March 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

Mon 9/6

7:30 p.m.-5:38 a.m.

1 stop8h 08m

Chicago O'Hare Intl

Sat 14/6

4:00 p.m.-10:26 p.m.

1 stop8h 26m

C$ 332

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 9/5

12:15 p.m.-4:44 p.m.

1 stop26h 29m

Chicago O'Hare Intl

Fri 16/5

5:30 p.m.-11:49 p.m.

1 stop8h 19m

C$ 386

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 30/5

5:45 a.m.-2:43 p.m.

1 stop6h 58m

Chicago O'Hare Intl

Mon 2/6

5:02 a.m.-10:32 p.m.

2 stops19h 30m

C$ 398

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 9/5

5:55 a.m.-6:37 p.m.

2 stops10h 42m

Chicago O'Hare Intl

Fri 16/5

5:30 p.m.-11:49 p.m.

1 stop8h 19m

C$ 493

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 24/4

11:10 a.m.-12:35 a.m.

2 stops11h 25m

Chicago O'Hare Intl

Thu 1/5

8:25 p.m.-6:55 p.m.

2 stops24h 30m

C$ 528

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 9/5

5:55 a.m.-6:45 p.m.

2 stops10h 50m

Chicago Midway

Fri 16/5

1:08 p.m.-11:49 p.m.

2 stops12h 41m

C$ 548

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 15/5

3:25 p.m.-11:59 p.m.

1 stop30h 34m

Chicago O'Hare Intl

Mon 19/5

6:00 a.m.-2:35 p.m.

1 stop10h 35m

C$ 659

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sun 29/6

7:00 a.m.-5:45 p.m.

2 stops8h 45m

Chicago Midway

Sat 5/7

9:21 a.m.-3:24 p.m.

2 stops8h 03m

C$ 1,030

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/3

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

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 26 March 2025.
To help decide which airline to fly from Kelowna to Chicago, see what other customers have to say about Alaska Airlines, Delta and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,792 reviews
Check prices

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,792 reviews
Alaska Airlines
8.0
Very good
9,792 reviews
Check prices

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,891 reviews
Alaska Airlines
8.0
Very good
9,792 reviews
Check prices

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,608 reviews
Alaska Airlines
8.0
Very good
9,792 reviews
Check prices

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
WestJet
7.2
Good
2,785 reviews
Alaska Airlines
8.0
Very good
9,792 reviews
Check prices

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Air Canada
7.0
Good
8,960 reviews
Alaska Airlines
8.0
Very good
9,792 reviews
Check prices

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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$ 332. Other airlines that can offer you cheap pricing are WestJet, from C$ 386, and United Airlines, from C$ 398. Air Canada is currently priced 52% below the average price you’ll pay for this route.

  • 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$ 355). 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 26 March 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 437AverageC$ 544FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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.

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!

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