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Cheap flights from Kelowna to Chicago from C$ 255

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 18/2. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — CHI
26 Jan — 2 Feb1
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 21 January 2025.

Round-trip from

C$ 379

One-way from

C$ 255

Popular in

March

Cheapest in

April

Average price

C$ 785
WestJet
  • WestJet
  • 13/2-27/2
  • 2 total stops
  • 17h 14m total
  • Kelowna to Chicago
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18/2
  • 18/2
  • 2 total stops
  • 34h 50m total
  • Kelowna to Chicago
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High demand for flights, 3% potential price rise
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Best time to find cheap flights, 3% potential price drop
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Average for round-trip flights in January 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 21 January 2025.

Thu 13/25:50 a.m.YLW - ORD
1 stop8h 06mWestJet
Thu 27/24:45 p.m.ORD - YLW
1 stop9h 08mWestJet
Deal found 20/1C$ 379
Mon 9/611:30 p.m.YLW - ORD
1 stop8h 29mAir Canada
Sat 14/68:25 p.m.ORD - YLW
1 stop15h 56mAir Canada
Deal found 20/1C$ 459
Thu 13/25:50 a.m.YLW - ORD
1 stop8h 06mMultiple Airlines
Thu 27/24:45 p.m.ORD - YLW
2 stops20h 10mMultiple Airlines
Deal found 20/1C$ 514
Thu 26/66:00 a.m.YLW - ORD
1 stop6h 49mUnited Airlines
Tue 1/75:00 a.m.ORD - YLW
2 stops16h 58mUnited Airlines
Deal found 20/1C$ 668
Fri 14/35:58 p.m.YLW - ORD
1 stop28h 01mAlaska Airlines
Tue 18/35:54 p.m.ORD - YLW
1 stop19h 10mAlaska Airlines
Deal found 20/1C$ 762
Mon 9/65:55 a.m.YLW - MDW
2 stops9h 06mDelta
Sat 14/62:00 p.m.MDW - YLW
2 stops11h 49mDelta
Deal found 20/1C$ 806
Thu 26/66:00 a.m.YLW - MDW
2 stops10h 03mWestJet
Tue 1/72:00 p.m.MDW - YLW
2 stops11h 49mWestJet
Deal found 20/1C$ 920
Sat 15/39:00 a.m.YLW - ORD
1 stop12h 53mDelta
Wed 19/37:30 a.m.ORD - YLW
1 stop7h 06mDelta
Deal found 20/1C$ 956
Thu 26/66:35 p.m.YLW - MDW
2 stops13h 45mMultiple Airlines
Tue 1/711:15 a.m.MDW - YLW
1 stop13h 10mMultiple Airlines
Deal found 20/1C$ 1,409

Find flights from Kelowna to Chicago within your budget

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 21 January 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 13/2

5:50 a.m.-3:56 p.m.

1 stop8h 06m

Chicago O'Hare Intl

Thu 27/2

4:45 p.m.-11:53 p.m.

1 stop9h 08m

C$ 379

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 9/6

11:30 p.m.-9:59 a.m.

1 stop8h 29m

Chicago O'Hare Intl

Sat 14/6

8:25 p.m.-10:21 a.m.

1 stop15h 56m

C$ 459

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 13/2

5:50 a.m.-3:56 p.m.

1 stop8h 06m

Chicago O'Hare Intl

Thu 27/2

4:45 p.m.-10:55 a.m.

2 stops20h 10m

C$ 514

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 26/6

6:00 a.m.-2:49 p.m.

1 stop6h 49m

Chicago O'Hare Intl

Tue 1/7

5:00 a.m.-7:58 p.m.

2 stops16h 58m

C$ 668

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 14/3

5:58 p.m.-11:59 p.m.

1 stop28h 01m

Chicago O'Hare Intl

Tue 18/3

5:54 p.m.-11:04 a.m.

1 stop19h 10m

C$ 762

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Mon 9/6

5:55 a.m.-5:01 p.m.

2 stops9h 06m

Chicago Midway

Sat 14/6

2:00 p.m.-11:49 p.m.

2 stops11h 49m

C$ 806

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 26/6

6:00 a.m.-6:03 p.m.

2 stops10h 03m

Chicago Midway

Tue 1/7

2:00 p.m.-11:49 p.m.

2 stops11h 49m

C$ 920

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sat 15/3

9:00 a.m.-11:53 p.m.

1 stop12h 53m

Chicago O'Hare Intl

Wed 19/3

7:30 a.m.-12:36 p.m.

1 stop7h 06m

C$ 956

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 26/6

6:35 p.m.-10:20 a.m.

2 stops13h 45m

Chicago Midway

Tue 1/7

11:15 a.m.-10:25 p.m.

1 stop13h 10m

C$ 1,409

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 18/2

9:00 a.m.-9:50 p.m.

2 stops34h 50m

C$ 255

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/1

Showing 1-10 of 15 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.

Travel insights for flights from Kelowna to Chicago

Get recent, data-driven insights about flights from Kelowna to Chicago including ideal travel times, pricing trends, and more.

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 21 January 2025.
To help decide which airline to fly from Kelowna to Chicago, see what other customers have to say about WestJet and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,706 reviews
Check prices

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Reviews

1 / 10

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
9,706 reviews
Alaska Airlines
8.0
Very good
9,706 reviews
Check prices

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Reviews

1 / 10

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
8,521 reviews
Alaska Airlines
8.0
Very good
9,706 reviews
Check prices

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Reviews

1 / 10

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
8,984 reviews
Alaska Airlines
8.0
Very good
9,706 reviews
Check prices

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Reviews

1 / 10

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
2,828 reviews
Alaska Airlines
8.0
Very good
9,706 reviews
Check prices

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Reviews

1 / 10

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
8,633 reviews
Alaska Airlines
8.0
Very good
9,706 reviews
Check prices

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Reviews

1 / 10

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$ 379. Other airlines that can offer you cheap pricing are Air Canada, from C$ 459, and United Airlines, from C$ 668. 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$ 279 on Alaska Airlines. Other airlines that offer cheap prices include Air Canada from C$ 377 and WestJet from C$ 484 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$ 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 21 January 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 440AverageC$ 531FlexibilityNo 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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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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