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Cheap flights from Kelowna to Chicago from C$ 176

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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — CHI
23 Jan — 30 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Kelowna to Chicago

Enter your travel dates to find the best prices.

Best flights from Kelowna to Chicago
Discover carefully curated flight deals from Kelowna to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 24 December 2025.

Thu 5/28:00 a.m.YLW - ORD
1 stop7h 10mAlaska Airlines
Mon 9/26:06 p.m.ORD - YLW
1 stop29h 08mAlaska Airlines
Deal found 21/12C$ 394
Tue 3/34:00 p.m.YLW - ORD
2 stops23h 03mMultiple Airlines
Fri 6/32:20 p.m.ORD - YLW
1 stop6h 48mMultiple Airlines
Deal found 22/12C$ 399
Thu 5/210:25 a.m.YLW - ORD
2 stops12h 33mUnited Airlines
Mon 9/22:00 p.m.ORD - YLW
1 stop10h 20mUnited Airlines
Deal found 23/12C$ 403
Thu 5/28:35 p.m.YLW - ORD
2 stops11h 31mAir Canada
Mon 9/211:15 a.m.ORD - YLW
2 stops13h 58mAir Canada
Deal found 23/12C$ 479
Thu 5/28:55 a.m.YLW - MDW
2 stops22h 13mDelta
Mon 9/21:51 p.m.MDW - YLW
2 stops12h 02mDelta
Deal found 21/12C$ 736
Tue 3/310:25 a.m.YLW - ORD
2 stops10h 27mUnited Airlines
Fri 6/37:57 p.m.ORD - YLW
2 stops19h 56mUnited Airlines
Deal found 22/12C$ 490

Find 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 24 December 2025.

Round-trip from

C$ 394

One-way from

C$ 176

Popular in

March

Cheapest in

June

Average price

C$ 443
Alaska Airlines
  • Alaska Airlines
  • 5/2-9/2
  • 2 total stops
  • 36h 18m total
  • Kelowna to Chicago
Search Deals
5/2
  • 5/2
  • 1 total stop
  • 8h 56m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 68 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 44 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 24 December 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

Thu 5/2

8:00 a.m.-5:10 p.m.

1 stop7h 10m

Chicago O'Hare Intl

Mon 9/2

6:06 p.m.-9:14 p.m.

1 stop29h 08m

C$ 394

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 3/3

4:00 p.m.-5:03 p.m.

2 stops23h 03m

Chicago O'Hare Intl

Fri 6/3

2:20 p.m.-7:08 p.m.

1 stop6h 48m

C$ 399

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 5/2

10:25 a.m.-12:58 a.m.

2 stops12h 33m

Chicago O'Hare Intl

Mon 9/2

2:00 p.m.-10:20 p.m.

1 stop10h 20m

C$ 403

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 5/2

8:35 p.m.-10:06 a.m.

2 stops11h 31m

Chicago O'Hare Intl

Mon 9/2

11:15 a.m.-11:13 p.m.

2 stops13h 58m

C$ 479

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Tue 3/3

10:25 a.m.-10:52 p.m.

2 stops10h 27m

Chicago O'Hare Intl

Fri 6/3

7:57 p.m.-1:53 p.m.

2 stops19h 56m

C$ 490

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 5/2

8:55 a.m.-9:08 a.m.

2 stops22h 13m

Chicago Midway

Mon 9/2

1:51 p.m.-11:53 p.m.

2 stops12h 02m

C$ 736

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 5/2

7:00 a.m.-5:56 p.m.

1 stop8h 56m

C$ 176

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 5/2

7:00 a.m.-3:58 p.m.

1 stop30h 58m

C$ 180

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sun 18/1

6:05 a.m.-7:24 p.m.

2 stops11h 19m

C$ 210

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sat 17/1

4:00 p.m.-7:24 p.m.

2 stops25h 24m

C$ 225

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/12

Showing 1-10 of 18 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

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

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

Calgary (YYC) – chosen by Cheapflights users on 25% of one-stop itineraries from Kelowna to Chicago on Cheapflights.

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

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

Toronto (YYZ) is the most affordable 1-stop option, with an average round-trip price of C$ 369.

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

Shortest average travel time for 1-stop one-way flights from Kelowna to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Calgary (YYC) have the shortest average one-way travel time for 1-stop routes: 6h 44m.

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

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

Flights via Calgary (YYC) offer the fastest connection on this route, with an average layover time of 1h 46m.

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 24 December 2025.
Read through reviews of airlines operating flights from Kelowna to Chicago, such as Air Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
10,553 reviews
Check prices

Entertainment

6.8

Boarding

7.3

Food

6.3

Comfort

7.1

Crew

7.8

Overall

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Jun 2025

YVR - YWG

Should allow a carry- on baggage in economy class. The first 4 rows after first class should be allowed to use the closest bathroom.
Air Canada
7.1
Good
10,553 reviews
Air Canada
7.1
Good
10,553 reviews
Check prices

Entertainment

6.8

Boarding

7.3

Food

6.3

Comfort

7.1

Crew

7.8

Overall

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Jun 2025

YVR - YWG

Should allow a carry- on baggage in economy class. The first 4 rows after first class should be allowed to use the closest bathroom.

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 0 different airlines.

  • How long is the flight from Kelowna to Chicago?

    Departing from Kelowna to Chicago will take you 7h 10m. There are 2565 km between Kelowna and Chicago. Both multi-stop and direct flights can be found to your destination and back.

  • 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.

See more FAQs

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