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Cheap flights from Kelowna to Chicago from C$ 222

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 29/8. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — CHI
20 Apr — 27 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 15 April 2025.

Round-trip from

C$ 222

Popular in

March

Cheapest in

August

Average price

C$ 531
WestJet
  • WestJet
  • 29/8-2/9
  • 2 total stops
  • 14h 03m total
  • Kelowna to Chicago
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Highest demand for flights based on searches. 6% potential increase in price (C$ 61 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).
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Average for round-trip flights in April 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 15 April 2025.

Fri 29/87:00 a.m.YLW - ORD
1 stop7h 44mWestJet
Tue 2/95:30 p.m.ORD - YLW
1 stop6h 19mWestJet
Deal found 15/4C$ 222
Tue 20/58:35 p.m.YLW - ORD
1 stop7h 11mAir Canada
Mon 16/67:35 p.m.ORD - YLW
1 stop15h 37mAir Canada
Deal found 15/4C$ 250
Fri 29/85:45 a.m.YLW - ORD
1 stop8h 57mUnited Airlines
Tue 2/98:50 a.m.ORD - YLW
2 stops15h 51mUnited Airlines
Deal found 15/4C$ 252
Mon 9/67:00 a.m.YLW - ORD
1 stop7h 44mDelta
Sat 14/67:40 a.m.ORD - YLW
2 stops11h 03mDelta
Deal found 15/4C$ 356
Tue 13/57:00 a.m.YLW - ORD
1 stop7h 44mMultiple Airlines
Sat 24/57:51 p.m.ORD - YLW
1 stop22h 52mMultiple Airlines
Deal found 15/4C$ 373
Fri 30/53:25 p.m.YLW - ORD
1 stop28h 58mAlaska Airlines
Fri 6/67:51 p.m.ORD - YLW
1 stop20h 44mAlaska Airlines
Deal found 15/4C$ 567
Fri 30/55:55 a.m.YLW - MDW
2 stops10h 50mDelta
Fri 6/610:25 a.m.MDW - YLW
2 stops10h 31mDelta
Deal found 15/4C$ 704
Fri 30/58:45 p.m.YLW - MDW
2 stops10h 55mWestJet
Fri 6/612:48 p.m.MDW - YLW
2 stops11h 01mWestJet
Deal found 15/4C$ 1,055

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 April 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

Fri 29/8

7:00 a.m.-4:44 p.m.

1 stop7h 44m

Chicago O'Hare Intl

Tue 2/9

5:30 p.m.-9:49 p.m.

1 stop6h 19m

C$ 222

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 20/5

8:35 p.m.-5:46 a.m.

1 stop7h 11m

Chicago O'Hare Intl

Mon 16/6

7:35 p.m.-9:12 a.m.

1 stop15h 37m

C$ 250

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 29/8

5:45 a.m.-4:42 p.m.

1 stop8h 57m

Chicago O'Hare Intl

Tue 2/9

8:50 a.m.-10:41 p.m.

2 stops15h 51m

C$ 252

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 9/6

7:00 a.m.-4:44 p.m.

1 stop7h 44m

Chicago O'Hare Intl

Sat 14/6

7:40 a.m.-4:43 p.m.

2 stops11h 03m

C$ 356

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 13/5

7:00 a.m.-4:44 p.m.

1 stop7h 44m

Chicago O'Hare Intl

Sat 24/5

7:51 p.m.-4:43 p.m.

1 stop22h 52m

C$ 373

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 30/5

3:25 p.m.-10:23 p.m.

1 stop28h 58m

Chicago O'Hare Intl

Fri 6/6

7:51 p.m.-2:35 p.m.

1 stop20h 44m

C$ 567

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 30/5

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

2 stops10h 50m

Chicago Midway

Fri 6/6

10:25 a.m.-6:56 p.m.

2 stops10h 31m

C$ 704

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 30/5

8:45 p.m.-9:40 a.m.

2 stops10h 55m

Chicago Midway

Fri 6/6

12:48 p.m.-9:49 p.m.

2 stops11h 01m

C$ 1,055

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 23/4

6:05 a.m.-2:43 p.m.

1 stop6h 38m

C$ 246

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Wed 23/4

6:20 a.m.-8:35 a.m.

3 stops24h 15m

C$ 268

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/4

Showing 1-10 of 11 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

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 15 April 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
9,876 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.1

Crew

8.5

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,876 reviews
Alaska Airlines
8.0
Very good
9,876 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.1

Crew

8.5

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,917 reviews
Alaska Airlines
8.0
Very good
9,876 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.1

Crew

8.5

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,658 reviews
Alaska Airlines
8.0
Very good
9,876 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.1

Crew

8.5

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
WestJet
7.2
Good
2,805 reviews
Alaska Airlines
8.0
Very good
9,876 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.1

Crew

8.5

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Air Canada
7.0
Good
9,134 reviews
Alaska Airlines
8.0
Very good
9,876 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.1

Crew

8.5

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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$ 222. Other airlines that can offer you cheap pricing are Air Canada, from C$ 250, and United Airlines, from C$ 252. WestJet is currently priced 66% 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 15 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 386AverageC$ 513FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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