ORD - YLW

$90 Find Cheap Flights from Chicago to Kelowna

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 10/19. 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 Kelowna

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

Sat, Feb 21 - Fri, Feb 27
Air Canada Logo
3:40 pm - 10:58 pmORD-YLW
9h 18m1 stop
Air Canada Logo
5:20 am - 2:41 pmYLW-ORD
7h 21m1 stop
$330Air Canada
Find Deal
Sat, Nov 1 - Sat, Nov 8
Air Canada Logo
3:40 pm - 10:58 pmORD-YLW
9h 18m1 stop
Air Canada Logo
9:00 pm - 2:41 pmYLW-ORD
15h 41m1 stop
$349Air Canada
Find Deal
Sat, Nov 1 - Sat, Nov 8
Alaska Airlines Logo
8:00 am - 3:02 pmORD-YLW
9h 02m1 stop
Alaska Airlines Logo
3:52 pm - 5:01 amYLW-ORD
11h 09m2 stops
$392Alaska Airlines
Find Deal
Sun, Nov 2 - Sun, Nov 9
Alaska Airlines Logo
5:00 am - 2:02 pmORD-YLW
11h 02m1 stop
Alaska Airlines Logo
3:52 pm - 5:01 amYLW-ORD
11h 09m2 stops
$407Alaska Airlines
Find Deal
Sat, Feb 21 - Fri, Feb 27
United Airlines Logo
6:35 am - 10:58 pmORD-YLW
18h 23m2 stops
United Airlines Logo
8:45 am - 5:09 pmYLW-ORD
6h 24m1 stop
$415United Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8
United Airlines Logo
1:55 pm - 10:58 pmORD-YLW
11h 03m2 stops
United Airlines Logo
5:20 am - 8:58 pmYLW-ORD
13h 38m2 stops
$430United Airlines
Find Deal
Sun, Nov 2 - Sun, Nov 9
Alaska Airlines Logo
5:00 am - 2:02 pmORD-YLW
11h 02m1 stop
Alaska Airlines Logo
3:52 pm - 2:25 pmYLW-ORD
20h 33m1 stop
$450Alaska Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8
Multiple Airlines Logo
7:43 pm - 7:55 pmORD-YLW
26h 12m2 stops
Multiple Airlines Logo
5:55 pm - 5:08 pmYLW-ORD
21h 13m3 stops
$458Multiple Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8
Multiple Airlines Logo
7:43 pm - 7:30 pmORD-YLW
25h 47m3 stops
Multiple Airlines Logo
5:55 pm - 5:08 pmYLW-ORD
21h 13m3 stops
$459Multiple Airlines
Find Deal

Everything you should know

Top airlines
Air Canada
Cheapest • from $330 (round-trip)
Alaska Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
November
Cheapest • 36% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$330
Overall average: $464
Air Canada
Sat 2/21Fri 2/27
ORD - YLW • 1 stop
Cheapest one-way
$90
WestJet
Sun 10/19
ORD - YLW • 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 Kelowna!
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’s the cheapest day of the week to fly from Chicago to Kelowna?

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

When flying from Chicago to Kelowna, you should consider leaving on a Friday and avoid Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Tuesdays and the most expensive ones on Thursdays.

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 November, where tickets cost $391 (return) on average. On the other hand, the most expensive months are March and April, where the average cost of round-trip tickets is $1,098 and $1,013 respectively.

Good to know

Low seasonJuly
Cheapest flight$90
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 80% increase in price.
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 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Kelowna was $90 for a one-way ticket and $330 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?

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Kelowna are Alaska Airlines and United Airlines. With an average price for the route of $630 and an overall rating of 8.0, Alaska Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $1,214 and an overall rating of 7.4.

  • 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 3 airlines serving 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.
8.0
Alaska AirlinesOverall score based on 10000 reviews
8.1Boarding
7.1Entertainment
7.8Comfort
8.5Crew
7.1Food
Airline reviews

The best thing were the seats It was too cold most of the time. The food was poor… The eggs were runny and potatoes were cold. The last time I flew first class we had a TV screen to watch movies but not this time The last time we had free alcohol, but not this time

6.0 GoodAnonymous, Sep 2025SEA - DTW
Read more Alaska Airlines reviews

The best thing were the seats It was too cold most of the time. The food was poor… The eggs were runny and potatoes were cold. The last time I flew first class we had a TV screen to watch movies but not this time The last time we had free alcohol, but not this time

All flights were on time. No crowded and had empty seats. All flight attendents were great.

Didn't buy food and did not use entertainment as these were not the purpose of my flight.

My flight was delayed 2 hours which led me to lose my connection. As a consequence, I had to spend hours changing flights and hotel reservations to arrange my arrival to Vancouver.

No Free Wifi and the flight was a tad late.

The plane was clean. They got us to the destination. It was very difficult to hear the announcements at the gate. The person was speaking way too quickly, and the sound system did not carry to all parts of the seating area at the gate. The flight left more than an hour late, which left many of the passengers missing connections.

Awesome. Great flight. Super nice people and I like the extra space

The first leg of the trip was excellent. Lovely flight attendants and comfortable plane. The second leg left a lot to be desired. The flight attendant was rude when I asked for a Diet Coke, the boarding required quite a long walk and the plane was crammed and uncomfortable.

Flight was delayed as it always is with Alaska airlines. Particularly to smaller airports. No AC on the plane so it was miserably hot.

Would have been nice if my flight was on time and I didn't miss my connection and had to spend the night in Seattle, losing one night at the VRBO I paid for in Sitka. And, my connecting flight was still at the gate when my flight was taxiing to it's gate. But, it took off. Too bad for me. I really can't believe you even want me to review or comment on my experience.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Short flight. Everything was fine except the flight was delayed twice for a total of an hour.

My flight from New York to Canada and Canada to Brisbane was canceled, so I had to take united airlines instead flight from New York to Dubai then layover in Dubai 8 hours then from Dubai to Brisbane it was extremely difficult for me , it was a nightmare flying with Canadian airlines unfortunately.

Real smooth and easy, Real good leg room in coach!

There labor disputes cancelled my flight less than 24 hours before my boarding time but there customer service/website was easy enough to navigate and they rebooked me for no upcharge.

Very bad, flight was cancelled due to strike and staff was unable to rebook us

They rescheduled me and I had no issues with the new flight

They could care less about you. Just under a 4 hour delay in Seattle, leading into a missed connection in Vancouver, which led to 2 more delays that added up to 3 more hours leaving us to have to sleep on the floor of the Toronto airport cause they don't help you find accomodations and they just book you on the next flight out. Took an additional 14 hours to get home. Always given the brush off to get rid of us. Worst airline ever

Both flights are delayed so I rate the whole experience as mediocre.

Flight was delayed by 1.5hrs. Once inside, people had their small handbags on the storage. The crew (male guy) was not helpful in making some space in the storage. Instead, he asked few bags to be checked-in and it was not a great experience. No attempt to help but just followed the things with a straight face. People had their literally small bags and he wouldnt not move from one storage to another even if there was space and would not let us do i as well. Once flight was on, they ran out of Orange juice, really running out of orange juice when the temp were 32.degrees outside. didnt made the sense. Onasking for a extra snack, he made a face as if he was giving me out of his pocket. if the flight was delayed, there could have an attempt to provide something extra incase people did asked.

Aircraft had technical issues. After 3 hours of trying to resolve, flight was cancelled. Was booked on a flight leaving 12 hours after intended departure. Now on 4 flights instead of 2 and a day late to my destination.

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

Information on your arrival and departure airports

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