ORD - YLW

$131 Find Cheap Flights from Chicago to Kelowna - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Kelowna departing on 9/11. 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, 0 bags

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Everything you should know

Cheapest round-trip
$301
WestJet
Thu 10/1Mon 10/5
ORD - YLW • 1 stop
Cheapest one-way
$131
WestJet
Fri 9/11
ORD - YLW • 1 stop
Top airlines
Cheapest • from $301 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
Not available
There are currently no direct flights between Chicago and Kelowna. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $448 (round-trip)
Shortest trip • 7h 43m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
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Good to know
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We hope you love your trip to Kelowna!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Kelowna (ORD-YLW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Kelowna 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 Chicago to Kelowna

Thu, Oct 1 - Mon, Oct 5
WestJet Logo
5:30 pm - 11:50 pmORD  Chicago O'Hare Intl-YLW Kelowna
8h 20m1 stop Calgary
WestJet Logo
8:15 pm - 4:40 pmYLW  Kelowna-ORD Chicago O'Hare Intl
18h 25m1 stop Calgary
$301WestJet
Thu, Oct 1 - Mon, Oct 5
WestJet Logo
5:30 pm - 11:50 pmORD  Chicago O'Hare Intl-YLW Kelowna
8h 20m1 stop Calgary
WestJet Logo
8:15 pm - 4:40 pmYLW  Kelowna-ORD Chicago O'Hare Intl
18h 25m1 stop Calgary
$316WestJet
Sun, Sep 13 - Sun, Sep 20
WestJet Logo
5:30 pm - 11:50 pmORD  Chicago O'Hare Intl-YLW Kelowna
8h 20m1 stop Calgary
WestJet Logo
8:15 pm - 4:40 pmYLW  Kelowna-ORD Chicago O'Hare Intl
18h 25m1 stop Calgary
$331WestJet
Thu, Sep 24 - Mon, Sep 28
WestJet Logo
5:30 pm - 11:50 pmORD  Chicago O'Hare Intl-YLW Kelowna
8h 20m1 stop Calgary
WestJet Logo
6:30 pm - 4:40 pmYLW  Kelowna-ORD Chicago O'Hare Intl
20h 10m1 stop Calgary
$351WestJet
Thu, Sep 24 - Mon, Sep 28
Air Canada Logo
3:40 pm - 11:27 pmORD  Chicago O'Hare Intl-YLW Kelowna
9h 47m1 stop Vancouver Intl
Air Canada Logo
10:50 pm - 9:00 amYLW  Kelowna-ORD Chicago O'Hare Intl
8h 10m1 stop Toronto Pearson Intl
$447Air Canada
Sat, Sep 19 - Sat, Sep 26
Air Canada Logo
3:40 pm - 10:47 pmORD  Chicago O'Hare Intl-YLW Kelowna
9h 07m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
10:50 pm - 9:00 amYLW  Kelowna-ORD Chicago O'Hare Intl
8h 10m1 stop Toronto Pearson Intl
$459Air Canada
Sat, Sep 19 - Sat, Sep 26
Air Canada Logo
3:40 pm - 10:47 pmORD  Chicago O'Hare Intl-YLW Kelowna
9h 07m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
10:50 pm - 9:00 amYLW  Kelowna-ORD Chicago O'Hare Intl
8h 10m1 stop Toronto Pearson Intl
$462Air Canada
Sat, Jan 30 - Sun, Feb 7
Alaska Airlines Logo
3:09 pm - 11:12 pmORD  Chicago O'Hare Intl-YLW Kelowna
9h 03m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
7:00 am - 12:09 pmYLW  Kelowna-ORD Chicago O'Hare Intl
28h 09m2 stops Seattle/Tacoma Intl Portland
$592Alaska Airlines
Fri, Jan 15 - Tue, Jan 19
Alaska Airlines Logo
5:55 pm - 3:47 pmORD  Chicago O'Hare Intl-YLW Kelowna
22h 52m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
8:00 am - 12:09 pmYLW  Kelowna-ORD Chicago O'Hare Intl
27h 09m2 stops Seattle/Tacoma Intl Portland
$593Alaska Airlines
Sat, Jan 30 - Sun, Feb 7
Alaska Airlines Logo
2:03 pm - 11:12 pmORD  Chicago O'Hare Intl-YLW Kelowna
10h 09m2 stops Portland Seattle/Tacoma Intl
Alaska Airlines Logo
7:00 am - 12:09 pmYLW  Kelowna-ORD Chicago O'Hare Intl
28h 09m2 stops Seattle/Tacoma Intl Portland
$598Alaska Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Kelowna flights

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

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Kelowna?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Kelowna, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Kelowna is April, where tickets cost $0 (return) on average. On the other hand, the most expensive months are September and October, where the average cost of round-trip tickets is $788 and $758 respectively.

Good to know

Low season

December

Cheapest flight

$131
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Chicago to Kelowna

When to book flights from Chicago to Kelowna

Are your dates flexible? Find out the best times to travel from Chicago to Kelowna 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 Chicago to Kelowna flights

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

    In the last 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Kelowna was $131 for a one-way ticket and $301 for a round-trip.

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

    A passport is required to fly from Chicago to Kelowna.

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

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

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

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

  • Which airline alliances offer flights from Chicago to Kelowna?

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

  • Which is the best airline for flights from Chicago to Kelowna, Alaska Airlines or Air Canada?

    The two airlines most popular with KAYAK users for flights from Chicago to Kelowna are Alaska Airlines and Air Canada. With an average price for the route of $419 and an overall rating of 7.9, Alaska Airlines is the most popular choice. Air Canada is also a great choice for the route, with an average price of $468 and an overall rating of 7.1.

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

    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 Chicago to Kelowna.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kelowna from Chicago 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 Chicago to Kelowna?

    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 Kelowna with an airline and back to Chicago with another airline. Booking your flights between Chicago and YLW 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 Chicago to Kelowna?

    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 Kelowna from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Chicago to Kelowna

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Kelowna. 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 Chicago to Kelowna? 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.
7.9
Alaska AirlinesOverall score based on 12774 reviews
7.0Food
7.8Comfort
8.1Boarding
8.5Crew
7.0Entertainment
Airline reviews

The seat was comfortable, but I paid for upgraded seats and they did not state that there was no outlets for devices.

2.0 MediocreAnonymous, Jul 2026
Read more Alaska Airlines reviews

The seat was comfortable, but I paid for upgraded seats and they did not state that there was no outlets for devices.

Extremely professional crew there are very friendly and first class. Everything worked well on the plane. Food was to be expected. Drinks were very good. Shout out to Charlie in first class who was an excellent flight attendant.

Thanks for all you do to keep us safe and on time!

I like flying Alaska Airlines. I think the staff are happy, the plane is comfortable, the entertainment reasonable, the food acceptable.

No WiFi. Terrible food. Very long walk to the gate and from the gate after landing. Gate changed without notice.

I really hate the seat assignment at the gate. I understand it is so families can sit together but it caused me and others a lot of unnecessary stress and confusion, enough for me to not fly Alaska again. The app is so awful that it did not even update my seat assignment on the boarding pass but sent me a notification of my seat... it showed in Apple Wallet but not in the Alaska app itself. That only made the stress worse. I think most people like myself prefer to know where they are seated at check in 24 hours before so they don't have to anxiously hang out at the gate the entire time. This is not a good use of your agents time either to be dealing with all of us asking where we are sitting. You should automatically assign the multiple seat purchases to be together before they check in and fill us solo travelers in those gaps as we check in.

Great. Went right to the desk and the people were helpful and kind. I was able to get my boarding pass in under 5minutes. They made sure I received the text.

The flight was delayed so we didn’t get into San Diego until almost 1 AM. Otherwise, it was lovely.

My flight got canceled never left san diego and miss out my fam event

Everyone was very friendly. And helpful. I loved flying to la and back. Great flight

The code sharing reservation with United was messed up requiring extra trip to airport to fix. Air Canada customer service 2.5 hours on hold and resolved nothing.

All was good except for the seats, not very comfy.

Liked the size of seats. Not much food offered given length of flight.

Everything but the actual plan was good. I would expect a 5hr flight would have at least chargers for mobile devices. Especially considering since the airplane had no screens for entertainment either. Seats were tighter than usual too.

I hadn’t noticed that I was on the budget carrier so I suppose it’s my fault. But that’s a long flight to have no entertainment and few food options,. Only one drink service offered during the entire flight.

I booked through Kayak for the first time. Unfortunately I was charged in US dollars. Only after booking did I see the tiny American flag on your website. There should have been a larger icon with a notice that I am in Kayak’s US site. I am Canadian, am flying in Canada and was disappointed that Kayak did not recognize this.

Air Can strike caused us to have to buy another ticket. Then at the end, it was wasted monye, because strike did not happen.

Flight was delayed, slow boarding,fully booked flight... No extra charge for beverages..

My seat was with screaming children all around. But the service was great

Business class is very lacking compared to than airlines like United, Swiss, American, Emirates BUT Air Canada price is less so makes sense - get what you pay for. Planes are old so design is cramped/ old fashioned, no blanket provided, toiletry bag ordinary, food was fine. BEST thing about Air Canada are their lounges in Canada - outstanding.

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

Information on your arrival and departure airports