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Cheap flights from Kelowna to Chicago from C$ 345

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 13/8. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — CHI
17 Jun — 24 Jun1
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 12 June 2025.

Round-trip from

C$ 345

Popular in

June

Cheapest in

December

Average price

C$ 852
WestJet
  • WestJet
  • 13/8-24/8
  • 2 total stops
  • 13h 03m total
  • Kelowna to Chicago
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Highest demand for flights based on searches. 12% potential increase in price (C$ 118 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 28 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 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 12 June 2025.

Wed 13/88:00 a.m.YLW - ORD
1 stop6h 44mWestJet
Sun 24/85:30 p.m.ORD - YLW
1 stop6h 19mWestJet
Deal found 10/6C$ 345
Mon 16/67:30 p.m.YLW - ORD
1 stop17h 13mAir Canada
Tue 24/63:35 p.m.ORD - YLW
1 stop8h 58mAir Canada
Deal found 11/6C$ 358
Mon 16/67:30 p.m.YLW - ORD
1 stop8h 08mUnited Airlines
Tue 24/65:02 a.m.ORD - YLW
2 stops9h 11mUnited Airlines
Deal found 11/6C$ 427
Tue 12/82:36 p.m.YLW - ORD
1 stop7h 23mAlaska Airlines
Sat 23/88:00 a.m.ORD - YLW
1 stop7h 57mAlaska Airlines
Deal found 10/6C$ 451
Mon 16/611:30 p.m.YLW - MDW
2 stops10h 59mDelta
Tue 24/69:21 a.m.MDW - YLW
2 stops8h 04mDelta
Deal found 11/6C$ 458
Fri 15/84:10 p.m.YLW - ORD
2 stops11h 30mMultiple Airlines
Thu 21/85:30 p.m.ORD - YLW
1 stop8h 09mMultiple Airlines
Deal found 10/6C$ 459
Sat 16/87:00 a.m.YLW - ORD
1 stop7h 44mDelta
Mon 25/811:05 a.m.ORD - YLW
2 stops12h 44mDelta
Deal found 10/6C$ 535
Wed 13/87:00 a.m.YLW - MDW
2 stops8h 37mWestJet
Sun 24/812:43 p.m.MDW - YLW
2 stops11h 06mWestJet
Deal found 10/6C$ 978
Mon 16/611:30 p.m.YLW - MDW
1 stop14h 54mMultiple Airlines
Tue 24/69:40 a.m.MDW - YLW
2 stops14h 11mMultiple Airlines
Deal found 11/6C$ 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 12 June 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

Wed 13/8

8:00 a.m.-4:44 p.m.

1 stop6h 44m

Chicago O'Hare Intl

Sun 24/8

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

1 stop6h 19m

C$ 345

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 12/8

8:35 p.m.-9:09 a.m.

2 stops10h 34m

Chicago O'Hare Intl

Wed 27/8

3:35 p.m.-10:48 p.m.

1 stop9h 13m

C$ 448

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 12/8

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

1 stop7h 23m

Chicago O'Hare Intl

Sat 23/8

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

1 stop7h 57m

C$ 451

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 15/8

4:10 p.m.-5:40 a.m.

2 stops11h 30m

Chicago O'Hare Intl

Thu 21/8

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

1 stop8h 09m

C$ 459

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 14/8

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

1 stop8h 08m

Chicago O'Hare Intl

Sun 24/8

7:15 a.m.-5:03 p.m.

2 stops11h 48m

C$ 520

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sat 16/8

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

1 stop7h 44m

Chicago O'Hare Intl

Mon 25/8

11:05 a.m.-9:49 p.m.

2 stops12h 44m

C$ 535

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 13/8

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

2 stops10h 42m

Chicago Midway

Tue 26/8

1:43 p.m.-11:30 p.m.

2 stops11h 47m

C$ 541

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 13/8

7:00 a.m.-5:37 p.m.

2 stops8h 37m

Chicago Midway

Sun 24/8

12:43 p.m.-9:49 p.m.

2 stops11h 06m

C$ 978

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

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 12 June 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
10,000 reviews
Check prices

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
WestJet
7.2
Good
2,868 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Air Canada
7.1
Good
9,537 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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$ 345. Other airlines that can offer you cheap pricing are Air Canada, from C$ 448, and Alaska Airlines, from C$ 451. WestJet is currently priced 45% 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$ 352). 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 12 June 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 368AverageC$ 504FlexibilityNo 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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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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