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Cheap flights from Chicago to Kelowna from C$ 155

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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YLW
5 Aug — 12 Aug1
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 31 July 2025.

Round-trip from

C$ 475

One-way from

C$ 155

Popular in

December

Cheapest in

March

Average price

C$ 754
Alaska Airlines
  • Alaska Airlines
  • 13/9-20/9
  • 2 total stops
  • 15h 13m total
  • Chicago to Kelowna
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WestJet
  • WestJet
  • 6/9
  • 2 total stops
  • 11h 50m total
  • Chicago to Kelowna
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Highest demand for flights based on searches. 11% potential increase in price (C$ 140 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 33 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 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 31 July 2025.

Sat 13/98:00 a.m.ORD - YLW
1 stop7h 57mAlaska Airlines
Sat 20/92:47 p.m.YLW - ORD
1 stop7h 16mAlaska Airlines
Deal found 29/7C$ 475
Sun 14/99:00 a.m.ORD - YLW
2 stops27h 00mMultiple Airlines
Wed 17/97:00 a.m.YLW - ORD
1 stop7h 43mMultiple Airlines
Deal found 30/7C$ 476
Wed 27/85:30 p.m.ORD - YLW
1 stop6h 19mWestJet
Sun 31/87:00 a.m.YLW - ORD
1 stop7h 44mWestJet
Deal found 31/7C$ 710
Fri 29/83:40 p.m.ORD - YLW
1 stop9h 08mAir Canada
Mon 1/98:35 p.m.YLW - ORD
1 stop16h 25mAir Canada
Deal found 30/7C$ 808
Fri 29/810:45 a.m.MDW - YLW
2 stops14h 31mMultiple Airlines
Mon 1/911:30 p.m.YLW - MDW
1 stop14h 54mMultiple Airlines
Deal found 30/7C$ 850
Mon 29/1210:00 p.m.ORD - YLW
2 stops21h 38mUnited Airlines
Mon 5/110:00 a.m.YLW - ORD
2 stops11h 57mUnited Airlines
Deal found 31/7C$ 884
Fri 29/85:30 p.m.ORD - YLW
1 stop8h 09mDelta
Mon 1/97:00 a.m.YLW - ORD
1 stop7h 43mDelta
Deal found 30/7C$ 1,311
Fri 29/89:15 a.m.MDW - YLW
2 stops15h 10mWestJet
Tue 2/98:15 p.m.YLW - MDW
3 stops19h 22mWestJet
Deal found 31/7C$ 1,341
Sat 13/91:43 p.m.MDW - YLW
2 stops11h 56mDelta
Sat 20/98:45 p.m.YLW - MDW
2 stops13h 03mDelta
Deal found 29/7C$ 1,643

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 31 July 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

Sat 13/9

8:00 a.m.-1:57 p.m.

1 stop7h 57m

Kelowna

Sat 20/9

2:47 p.m.-12:03 a.m.

1 stop7h 16m

C$ 475

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sun 14/9

9:00 a.m.-10:00 a.m.

2 stops27h 00m

Kelowna

Wed 17/9

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

1 stop7h 43m

C$ 476

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Wed 27/8

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

1 stop6h 19m

Kelowna

Sun 31/8

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

1 stop7h 44m

C$ 710

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Fri 29/8

3:40 p.m.-10:48 p.m.

1 stop9h 08m

Kelowna

Mon 1/9

8:35 p.m.-3:00 p.m.

1 stop16h 25m

C$ 808

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 29/8

10:45 a.m.-11:16 p.m.

2 stops14h 31m

Kelowna

Mon 1/9

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

1 stop14h 54m

C$ 850

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Mon 29/12

10:00 p.m.-5:38 p.m.

2 stops21h 38m

Kelowna

Mon 5/1

10:00 a.m.-11:57 p.m.

2 stops11h 57m

C$ 884

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Fri 29/8

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

1 stop8h 09m

Kelowna

Mon 1/9

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

1 stop7h 43m

C$ 1,311

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 29/8

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

2 stops15h 10m

Kelowna

Tue 2/9

8:15 p.m.-5:37 p.m.

3 stops19h 22m

C$ 1,341

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sat 13/9

1:43 p.m.-11:39 p.m.

2 stops11h 56m

Kelowna

Sat 20/9

8:45 p.m.-11:48 a.m.

2 stops13h 03m

C$ 1,643

ChicagoKelowna

ORD - YLW

ORDYLW

Chicago O'Hare Intl

Sat 6/9

1:40 p.m.-11:30 p.m.

2 stops11h 50m

C$ 155

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/7

Showing 1-10 of 17 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 December is currently the most expensive (average of C$ 238). 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.

What’s the top layover airport for flights from Chicago to Kelowna?

Share of one-stop round-trip flights from Chicago to Kelowna chosen by Cheapflights users in the past 12 months, using the same layover each way.

Vancouver (YVR) – chosen by Cheapflights users on 67% of one-stop itineraries from Chicago to Kelowna on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Kelowna?

Average round-trip fare for 1-stop flights from Chicago to Kelowna, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Vancouver (YVR) is the most affordable 1-stop option, with an average round-trip price of C$ 480.

What’s the fastest layover option from Chicago to Kelowna?

Shortest average travel time for 1-stop one-way flights from Chicago to Kelowna, 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: 9h 03m.

Which airport typically offers the quickest layover for flights from Chicago to Kelowna?

Average layover duration for 1-stop one-way flights from Chicago to Kelowna, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 3h 08m.

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 31 July 2025.
Read through reviews of airlines operating flights from Chicago to Kelowna, such as Alaska Airlines,Delta, andUnited Airlines. 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

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,900 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
WestJet
7.2
Good
2,978 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Air Canada
7.1
Good
9,851 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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$ 475. Other airlines that can offer you cheap pricing are WestJet, from C$ 710, and Air Canada, from C$ 808. Alaska Airlines is priced at 38% 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 WestJet, with whom users have recently found tickets for as low as C$ 155. However, be on the lookout for offers from Alaska Airlines and Air Canada, 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 December is currently the most expensive (average of C$ 238). 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 Kelowna?

Book flights to Kelowna if you plan to visit one of these locations
Salmon Arm
West Kelowna
Big White

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