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CA $288 Cheap Flights from Kelowna (YLW) to Chicago (CHI)

View CA $288 flight on Sun, Dec 13, 2026

Popular airlines from Kelowna Intl. Airport (YLW) to Chicago

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  • Find the cheapest flights on Expedia from Kelowna (YLW) to Chicago (CHI). Flight ticket prices change frequently based on availability and demand. We send price‑drop alerts to make air travel simple and flexible. The lowest one-way fare found on Expedia for this route in the past 7 days starts at CA $288 for travel on December 13, 2026.

    Cheap Flights from Kelowna to Chicago (YLW-CHI)

    Prices were available within the past 7 days and start at CA $288 for one-way flights and CA $519 for roundtrip, for the period specified. Prices and availability are subject to change.

    All deals

    One way

    Roundtrip

    Select Air Canada flight, departing Tue, Apr 27 from Kelowna to Chicago, returning Wed, May 12, priced at CA $519 Found 2 days ago

    Tue, Apr 27 - Wed, May 12 · YLW · ORD · Roundtrip

    Select Air Canada flight, departing Mon, Apr 26 from Kelowna to Chicago, returning Wed, May 12, priced at CA $530 Found 2 days ago

    Mon, Apr 26 - Wed, May 12 · YLW · ORD · Roundtrip

    Select Air Canada flight, departing Fri, Jan 22 from Kelowna to Chicago, returning Sun, Jan 24, priced at CA $537 Found 2 days ago

    Fri, Jan 22 - Sun, Jan 24 · YLW · ORD · Roundtrip

    Select Air Canada flight, departing Mon, Mar 29 from Kelowna to Chicago, returning Mon, Apr 19, priced at CA $543 Found 2 days ago

    Mon, Mar 29 - Mon, Apr 19 · YLW · ORD · Roundtrip

    Select Air Canada flight, departing Wed, Mar 24 from Kelowna to Chicago, returning Fri, Apr 9, priced at CA $548 Found 2 days ago

    Wed, Mar 24 - Fri, Apr 9 · YLW · ORD · Roundtrip

    Select Air Canada flight, departing Fri, Apr 9 from Kelowna to Chicago, returning Sat, Apr 17, priced at CA $551 Found 23 hours ago

    Fri, Apr 9 - Sat, Apr 17 · YLW · ORD · Roundtrip

    Select WestJet flight, departing Sun, Apr 25 from Kelowna to Chicago, returning Sun, May 2, priced at CA $578 Found 1 day ago

    Sun, Apr 25 - Sun, May 2 · YLW · ORD · Roundtrip

    Select Alaska Airlines flight, departing Fri, Dec 4 from Kelowna to Chicago, returning Mon, Dec 7, priced at CA $582 Found 2 days ago

    Fri, Dec 4 - Mon, Dec 7 · YLW · ORD · Roundtrip

    Select United flight, departing Wed, Jan 20 from Kelowna to Chicago, returning Thu, Jan 21, priced at CA $629 Found 4 hours ago

    Wed, Jan 20 - Thu, Jan 21 · YLW · ORD · Roundtrip

    Select Delta flight, departing Sun, Dec 6 from Kelowna to Chicago, returning Sun, Dec 13, priced at CA $748 Found 1 day ago

    Sun, Dec 6 - Sun, Dec 13 · YLW · ORD · Roundtrip

    Alternative airports near Chicago

    Prices were available within the past 7 days. Prices and availability are subject to change.

    Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from CA $882

    23 min

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    Kelowna to Chicago Flights

    The easy way to book your flights from Kelowna to Chicago

    With Expedia, it’s simple to find and book flights to Chicago from Kelowna whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 5 airlines that cover this route. There are nonstop flights to CHI-All Airports, too.

    Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Kelowna to Chicago today, tomorrow, or this week.

    Save dollars with cheap flights from Kelowna Intl., YLW to CHI-All Airports, CHI

    Sort your search results by price to find great deals on your flight from Kelowna to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Kelowna currently is just CA $519 rising to CA $748.

    Here are more money-saving tips:

    • Fly in April when flight prices are normally at their lowest
    • Book about a month to 6 weeks before you travel for the best prices to Chicago
    • Avoid peak season and weekends when flights can cost more
    • Early morning and late-night flights are sometimes cheaper, so try varying your travel times
    • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!

    Reasons to choose Expedia for your flight to Chicago from Kelowna

    Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

    Travel information

    Origin airportKelowna Intl. Airport
    Destination airportChicago Midway Airport
    Distance2,588 km away
    Roundtrip priceCA $519

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