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Cheap flights from Chicago to Kelowna from C$ 264

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 27/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YLW
17 Jun — 24 Jun1
1 adult

Cheap flight deals from Chicago to Kelowna

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Kelowna (YLW). 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 12 June 2025.

Round-trip from

C$ 394

One-way from

C$ 264

Popular in

December

Cheapest in

June

Average price

C$ 200
WestJet
  • WestJet
  • 19/9-22/9
  • 2 total stops
  • 14h 02m total
  • Chicago to Kelowna
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27/7
  • 27/7
  • 3 total stops
  • 28h 49m total
  • Chicago to Kelowna
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Highest demand for flights based on searches. 27% potential increase in price (C$ 361 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease (C$ 66 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find flight deals from Chicago to Kelowna

Cheapest flights from Chicago to Kelowna
Explore the most affordable flight options available from Chicago to Kelowna. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 12 June 2025.

Fri 19/95:30 p.m.ORD - YLW
1 stop6h 19mWestJet
Mon 22/97:00 a.m.YLW - ORD
1 stop7h 43mWestJet
Deal found 10/6C$ 394
Mon 7/75:30 p.m.ORD - YLW
1 stop6h 19mMultiple Airlines
Mon 14/77:00 a.m.YLW - ORD
2 stops12h 30mMultiple Airlines
Deal found 11/6C$ 424
Sat 26/73:50 p.m.ORD - YLW
1 stop8h 38mAir Canada
Sat 2/811:25 p.m.YLW - ORD
1 stop7h 44mAir Canada
Deal found 11/6C$ 479
Fri 27/69:32 p.m.ORD - YLW
2 stops18h 41mUnited Airlines
Mon 30/68:35 p.m.YLW - ORD
1 stop7h 03mUnited Airlines
Deal found 10/6C$ 509
Fri 19/99:15 a.m.MDW - YLW
1 stop15h 10mMultiple Airlines
Mon 22/911:30 p.m.YLW - MDW
1 stop14h 54mMultiple Airlines
Deal found 10/6C$ 561
Fri 19/99:20 a.m.MDW - YLW
2 stops11h 35mDelta
Mon 22/95:55 a.m.YLW - MDW
2 stops13h 49mDelta
Deal found 10/6C$ 893
Sun 6/79:21 a.m.MDW - YLW
2 stops11h 35mWestJet
Sun 13/76:30 p.m.YLW - MDW
2 stops13h 15mWestJet
Deal found 11/6C$ 1,232
Sat 5/74:20 p.m.ORD - YLW
2 stops9h 10mDelta
Mon 14/710:40 a.m.YLW - ORD
2 stops11h 16mDelta
Deal found 10/6C$ 1,272
Wed 9/712:59 a.m.ORD - YLW
2 stops14h 47mAlaska Airlines
Thu 17/72:36 p.m.YLW - ORD
1 stop7h 23mAlaska Airlines
Deal found 10/6C$ 1,314

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Kelowna 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 12 June 2025.
Use the filters below to find and compare flights from Chicago to Kelowna that are best for you.

Fly from

Chicago

Fly to

Kelowna

Route

Depart

Return

Price

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Fri 19/9

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

1 stop6h 19m

Kelowna

Mon 22/9

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

1 stop7h 43m

C$ 394

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Mon 7/7

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

1 stop6h 19m

Kelowna

Mon 14/7

7:00 a.m.-9:30 p.m.

2 stops12h 30m

C$ 424

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sat 26/7

3:50 p.m.-10:28 p.m.

1 stop8h 38m

Kelowna

Sat 2/8

11:25 p.m.-9:09 a.m.

1 stop7h 44m

C$ 479

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Fri 27/6

9:32 p.m.-2:13 p.m.

2 stops18h 41m

Kelowna

Mon 30/6

8:35 p.m.-5:38 a.m.

1 stop7h 03m

C$ 509

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 19/9

9:15 a.m.-10:25 p.m.

1 stop15h 10m

Kelowna

Mon 22/9

11:30 p.m.-4:24 p.m.

1 stop14h 54m

C$ 561

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 19/9

9:20 a.m.-6:55 p.m.

2 stops11h 35m

Kelowna

Mon 22/9

5:55 a.m.-9:44 p.m.

2 stops13h 49m

C$ 893

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 6/7

9:21 a.m.-6:56 p.m.

2 stops11h 35m

Kelowna

Sun 13/7

6:30 p.m.-9:45 a.m.

2 stops13h 15m

C$ 1,232

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sat 5/7

4:20 p.m.-11:30 p.m.

2 stops9h 10m

Kelowna

Mon 14/7

10:40 a.m.-11:56 p.m.

2 stops11h 16m

C$ 1,272

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Wed 9/7

12:59 a.m.-1:46 p.m.

2 stops14h 47m

Kelowna

Thu 17/7

2:36 p.m.-11:59 p.m.

1 stop7h 23m

C$ 1,314

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 27/7

6:20 a.m.-9:09 a.m.

3 stops28h 49m

C$ 264

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/6

Showing 1-10 of 15 results
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Best time to book a flight from Chicago to Kelowna

Have a flexible travel schedule? Discover the best time to fly to Kelowna from Chicago 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 Chicago to Kelowna

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

Currently, October is the cheapest month in which you can book a flight from Chicago to Kelowna (average of C$ 137). Flying from Chicago to Kelowna in March is currently the most expensive (average of C$ 237). 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.

Rainfall in Kelowna by month

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

In terms of precipitation, rainfall in Kelowna ranges from 19.0 - 46.0 mm per month. June is typically the wettest month, when rainfall can reach 46.0 mm. February is typically the driest time to visit Kelowna when rainfall is around 19.0 mm.

Temperature in Kelowna by month

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

If weather is an important factor for your trip to Kelowna, 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 20.0 C. Travellers hoping to avoid the cold should look outside of December, when temperatures are typically at their lowest (around -3.0 C).

Reviews of airlines servicing Kelowna

Get insights into the airlines that provide service to Kelowna. 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 Kelowna. Reviews last updated 12 June 2025.
Read through reviews of airlines operating flights from Chicago to Kelowna, such as Alaska Airlines, Delta and United Airlines. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
WestJet
7.2
Good
2,868 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Air Canada
7.1
Good
9,531 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Kelowna. 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 into for flights to Kelowna from Chicago?

    Located just 11.2 km from the city centre, Kelowna is the airport most travellers will use when flying to Kelowna from Chicago. Booking flights from Chicago to Kelowna (YLW) should be relatively easy as there are 0 daily inbound flights from Chicago from 0 different airlines.

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

    Cheapflights users have booked flights from Chicago to Kelowna round-trip from C$ 394. Other airlines that can offer you cheap pricing are Air Canada, from C$ 479, and United Airlines, from C$ 509. WestJet is priced at 44% lower than the current average price of a flight leaving 3 months from now.

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

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as C$ 287. However, be on the lookout for offers from Air Canada and WestJet, as they are both options that can get you from Chicago to Kelowna for a low price.

  • Can I find deals for flights from Chicago to Kelowna that include hotel bookings?

    Yes. In addition to deals on Chicago to Kelowna flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Kelowna?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Kelowna.

  • Can I find deals for business class flights from Chicago to Kelowna?

    Yes. Cheapflights offers flight deals from Chicago to Kelowna 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 Chicago to Kelowna?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Kelowna (average of C$ 137). Flying from Chicago to Kelowna in March is currently the most expensive (average of C$ 237). 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

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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