YLW - ORD

$134 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 11/28. 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.

Recent round-trip flight deals from Kelowna to Chicago

Sat, Oct 25 - Mon, Oct 27
WestJet Logo
7:00 am - 4:43 pmYLW-ORD
7h 43m1 stop
WestJet Logo
2:20 pm - 7:10 pmORD-YLW
6h 50m1 stop
$236WestJet
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Fri, Feb 27 - Mon, Mar 2
WestJet Logo
5:20 am - 1:35 pmYLW-ORD
6h 15m1 stop
WestJet Logo
2:20 pm - 7:08 pmORD-YLW
6h 48m1 stop
$239WestJet
Find Deal
Wed, Feb 25 - Mon, Mar 2
Air Canada Logo
5:20 am - 2:41 pmYLW-ORD
7h 21m1 stop
Air Canada Logo
3:40 pm - 11:08 pmORD-YLW
9h 28m1 stop
$243Air Canada
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Thu, Feb 26 - Mon, Mar 2
Air Canada Logo
5:20 am - 2:41 pmYLW-ORD
7h 21m1 stop
Air Canada Logo
2:00 pm - 11:08 pmORD-YLW
11h 08m2 stops
$257Air Canada
Find Deal
Fri, Oct 24 - Mon, Oct 27
Multiple Airlines Logo
5:50 pm - 4:43 pmYLW-ORD
20h 53m1 stop
Multiple Airlines Logo
2:20 pm - 7:10 pmORD-YLW
6h 50m1 stop
$263Multiple Airlines
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Thu, Feb 26 - Tue, Mar 3
Alaska Airlines Logo
1:20 pm - 11:59 pmYLW-ORD
8h 39m1 stop
Alaska Airlines Logo
2:05 pm - 9:04 pmORD-YLW
8h 59m2 stops
$286Alaska Airlines
Find Deal
Sat, Oct 25 - Tue, Oct 28
Multiple Airlines Logo
7:00 am - 4:43 pmYLW-ORD
7h 43m1 stop
Multiple Airlines Logo
8:00 am - 3:02 pmORD-YLW
9h 02m1 stop
$307Multiple Airlines
Find Deal
Sat, Feb 28 - Tue, Mar 3
Alaska Airlines Logo
8:50 am - 5:50 pmYLW-ORD
7h 00m1 stop
Alaska Airlines Logo
2:05 pm - 9:04 pmORD-YLW
8h 59m2 stops
$313Alaska Airlines
Find Deal
Thu, Nov 6 - Tue, Nov 11
United Airlines Logo
5:20 am - 2:41 pmYLW-ORD
7h 21m1 stop
United Airlines Logo
3:40 pm - 11:08 pmORD-YLW
9h 28m1 stop
$323United Airlines
Find Deal
Thu, Feb 26 - Sun, Mar 1
United Airlines Logo
8:45 am - 5:09 pmYLW-ORD
6h 24m1 stop
United Airlines Logo
3:40 pm - 11:08 pmORD-YLW
9h 28m1 stop
$333United Airlines
Find Deal

Everything you should know

Top airlines
WestJet
Cheapest • from $236 (round-trip)
Air Canada
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Cheapest round-trip
$236
Typical prices: $274-454
WestJet
Sat 10/25Mon 10/27
YLW - ORD • 1 stop
Cheapest one-way
$134
WestJet
Fri 11/28
YLW - ORD • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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.

How much is a round-trip flight from Kelowna to Chicago O'Hare Intl Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Kelowna to Chicago O'Hare Intl Airport departing in October.

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.

Find deals

Good to know

Low seasonJune
Cheapest flight$134
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly with an average 18% 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 $134 for a one-way ticket and $236 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 is the only airline alliance operating flights between Kelowna and Chicago.

  • 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 10000 reviews
7.3Boarding
7.1Comfort
6.3Food
7.8Crew
6.8Entertainment
Airline reviews

I’ve wasted 7 hours of my time because of the delayed. ;(

2.0 MediocreAnonymous, Sep 2025YLW - YVR
Read more Air Canada reviews

I’ve wasted 7 hours of my time because of the delayed. ;(

I had boarding pass on my phone. Husband and I were seated together. Agent printed out boarding passes and we were separated for the flight

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…

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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