YLW - ORD

$132 Find Cheap Flights from Kelowna to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Kelowna to Chicago departing on 10/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Kelowna to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Kelowna to Chicago, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Kelowna to Chicago (YLW-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Kelowna to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Kelowna to Chicago

Tue, Nov 4 - Sun, Nov 9
Air Canada Logo
5:20 am - 2:41 pmYLW-ORD
7h 21m1 stop
Air Canada Logo
3:40 pm - 10:58 pmORD-YLW
9h 18m1 stop
$270Air Canada
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Tue, Nov 4 - Sun, Nov 9
United Airlines Logo
8:45 am - 5:10 pmYLW-ORD
6h 25m1 stop
United Airlines Logo
6:15 am - 10:58 pmORD-YLW
18h 43m2 stops
$350United Airlines
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Tue, Nov 4 - Sun, Nov 9
United Airlines Logo
8:45 am - 11:59 pmYLW-ORD
13h 14m2 stops
United Airlines Logo
6:15 am - 5:38 pmORD-YLW
13h 23m2 stops
$356United Airlines
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Wed, Oct 8 - Mon, Oct 13
Alaska Airlines Logo
2:46 pm - 11:59 pmYLW-ORD
7h 13m1 stop
Alaska Airlines Logo
6:00 am - 1:56 pmORD-YLW
9h 56m1 stop
$412Alaska Airlines
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Wed, Oct 8 - Mon, Oct 13
Logo
7:00 am - 8:50 pmYLW-ORD
11h 50m2 stops
Logo
6:00 am - 1:56 pmORD-YLW
9h 56m1 stop
$435
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Wed, Oct 8 - Mon, Oct 13
United Airlines Logo
5:55 am - 5:13 amYLW-ORD
21h 18m2 stops
United Airlines Logo
5:01 am - 10:31 pmORD-YLW
19h 30m2 stops
$471United Airlines
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Thu, Aug 28 - Mon, Sep 1
WestJet Logo
7:00 am - 4:44 pmYLW-ORD
7h 44m1 stop
WestJet Logo
7:45 am - 5:47 pmORD-YLW
12h 02m2 stops
$944WestJet
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Thu, Aug 28 - Mon, Sep 1
WestJet Logo
6:00 am - 4:44 pmYLW-ORD
8h 44m2 stops
WestJet Logo
6:10 am - 7:24 pmORD-YLW
15h 14m2 stops
$1,081WestJet
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Thu, Aug 28 - Mon, Sep 1
Logo
2:47 pm - 7:03 amYLW-ORD
14h 16m1 stop
Logo
6:20 am - 11:25 amORD-YLW
31h 05m2 stops
$1,409
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Thu, Aug 28 - Mon, Sep 1
Alaska Airlines Logo
2:47 pm - 11:59 pmYLW-ORD
7h 12m1 stop
Alaska Airlines Logo
8:00 am - 1:57 pmORD-YLW
7h 57m1 stop
$1,439Alaska Airlines
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Booking Insights

KAYAK's insights & trends for Kelowna to Chicago flights

Get data-powered insights and trends into flights from Kelowna to Chicago to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Kelowna to Chicago?

The average price of all round-trip flights from Kelowna to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Chicago on a Tuesday and more expensive on a Thursday. On your return trip to Kelowna, you should consider flying back on a Friday, and avoid Mondays for better deals.

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Good to know

Low seasonJune
Cheapest flight$132
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Kelowna to Chicago

When to book flights from Kelowna to Chicago

Are your dates flexible? Find out the best times to travel from Kelowna to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Kelowna to Chicago flights

  • What is the cheapest flight from Kelowna to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Kelowna to Chicago O'Hare Intl Airport was $132 for a one-way ticket and $270 for a round-trip.

  • Do I need a passport to fly between Kelowna and Chicago?

    Yes

  • Which airports will I be using when flying from Kelowna to Chicago?

    Kelowna airport is called Kelowna and the only airport in Chicago is Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Kelowna to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Kelowna to Chicago?

    Star Alliance, SkyTeam, and oneworld are the airline alliances operating flights between Kelowna and Chicago, with Star Alliance being the most commonly used for this route.

  • How does KAYAK find such low prices on flights from Kelowna to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Kelowna to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Kelowna to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Kelowna is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Kelowna to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Kelowna with another airline. Booking your flights between Kelowna and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Kelowna to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Kelowna up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Kelowna to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Kelowna to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Kelowna to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
Air CanadaOverall score based on 9949 reviews
7.8Crew
7.3Boarding
6.3Food
7.1Comfort
6.8Entertainment
Airline reviews

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

4.0 OkayAnonymous, Jul 2025YVR - ORD
Read more Air Canada reviews

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

Very bad service the way back we was on the way for r two days very bad condition and waiting for luggage till now

United had no (zero) record of our flight. It took over an hour of us standing in line with surly employee while others waited to get resolved. I have never experienced such poor service and poor empathy.

Good overall but I’m 5’10 and seating is always tight

Or the greatest and it ended up picking us up from Chicago to Toronto not sure who was tesponsible for the 4 hr delay. United should have been properly prepared for a scheduled flight from Austin to Chicago and they were not.

My flight was overbooked and they would not let me board. I had to book another flight and pay the full amount of that flight. I did not get any help at all from Air Canada or United Airlines.

Everything was made rather simple, so I appreciate that. All the people I dealt with from entering the airport in Jacksonville to my lonnnnnnng walk to my next gate in Chicago were excellent and very helpful.

Terrible. 3 missed flights and 24 hours delayed with lost bag and promised $100 compensation from United and absolutely nothing from them…

flight was delayed 6 hours for weather, then cancelled because of the crash in toronto, but none of the links to cancel or rebook my flights are working

Ok Did not like that the second leg of flight was moved earlier making it a rush to make it

Everything you need to know for your flight from Kelowna to Chicago

Information on your arrival and departure airports

Kelowna (YLW)
O'Hare Intl (ORD)

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