ORD - YLW

$202 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 8/19. 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, 0 bags

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$372
WestJet
Thu 10/1Mon 10/5
ORD - YLW • 1 stop
Cheapest one-way
$202
WestJet
Wed 8/19
ORD - YLW • 1 stop
Top airlines
Cheapest • from $372 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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 48m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
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 - 10:05 pm
ORD
-
YLW
6h 35m
1 stop
WestJet Logo
7:50 am - 4:40 pm
YLW
-
ORD
6h 50m
1 stop
$372WestJet
Tue, Aug 11 - Fri, Aug 14
WestJet Logo
5:30 pm - 11:50 pm
ORD
-
YLW
8h 20m
1 stop
WestJet Logo
7:50 am - 4:40 pm
YLW
-
ORD
6h 50m
1 stop
$401WestJet
Tue, Sep 29 - Fri, Oct 2
WestJet Logo
5:30 pm - 10:05 pm
ORD
-
YLW
6h 35m
1 stop
WestJet Logo
6:05 am - 4:40 pm
YLW
-
ORD
8h 35m
1 stop
$421WestJet
Tue, Sep 29 - Fri, Oct 2
Air Canada Logo
3:40 pm - 11:12 pm
ORD
-
YLW
9h 32m
1 stop
Air Canada Logo
8:30 pm - 1:23 pm
YLW
-
ORD
14h 53m
2 stops
$434Air Canada
Wed, Sep 30 - Mon, Oct 5
Air Canada Logo
2:15 pm - 10:27 pm
ORD
-
YLW
10h 12m
1 stop
Air Canada Logo
11:30 pm - 9:00 am
YLW
-
ORD
7h 30m
1 stop
$437Air Canada
Tue, Sep 29 - Fri, Oct 2
Air Canada Logo
2:15 pm - 11:12 pm
ORD
-
YLW
10h 57m
2 stops
Air Canada Logo
8:30 pm - 1:23 pm
YLW
-
ORD
14h 53m
2 stops
$448Air Canada
Thu, Aug 6 - Mon, Aug 10
WestJet Logo
5:30 pm - 11:50 pm
ORD
-
YLW
8h 20m
1 stop
WestJet Logo
8:15 pm - 4:40 pm
YLW
-
ORD
18h 25m
1 stop
$456WestJet
Tue, Aug 11 - Fri, Aug 14
Multiple Airlines Logo
2:12 pm - 12:56 pm
ORD
-
YLW
24h 44m
2 stops
Multiple Airlines Logo
6:05 am - 4:40 pm
YLW
-
ORD
8h 35m
1 stop
$460Multiple Airlines
Tue, Jul 7 - Tue, Jul 14
Multiple Airlines Logo
5:30 pm - 10:05 pm
ORD
-
YLW
6h 35m
1 stop
Multiple Airlines Logo
1:46 pm - 11:59 pm
YLW
-
ORD
8h 13m
1 stop
$462Multiple Airlines
Tue, Jul 7 - Tue, Jul 14
Multiple Airlines Logo
5:30 pm - 11:50 pm
ORD
-
YLW
8h 20m
1 stop
Multiple Airlines Logo
1:46 pm - 11:59 pm
YLW
-
ORD
8h 13m
1 stop
$464Multiple 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 October and August, where the average cost of round-trip tickets is $758 and $658 respectively.

Good to know

Low seasonDecember
Cheapest flight$202
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly and prices are also 19% 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 $202 for a one-way ticket and $372 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 $450 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 12509 reviews
8.5Crew
7.0Entertainment
7.8Comfort
8.1Boarding
7.0Food
Airline reviews

The agents were super helpful. I was traveling with my mother inlaw who needed whell chair assisstance. The help and accomodation from the checkin crew, to the boarding crew and inflight crew was excellent.

10.0 ExcellentAnonymous, Jun 2026
IAD - SEA
Read more Alaska Airlines reviews

The agents were super helpful. I was traveling with my mother inlaw who needed whell chair assisstance. The help and accomodation from the checkin crew, to the boarding crew and inflight crew was excellent.

People were friendly. Flight was a little delayed. Maybe I missed the reason for it. Overall a nice experience.

Completely full flight. Boarding was smooth, but people didn’t listen about use of overhead bins which is typical. We pre-purchased a snack which was tasty. Drinks were good and plentiful. Flight left late because previous flight was delayed.

The flight itself was great. But we had to wait over an hour to deplane so I missed my train. Not the crews fault. They were wonderful!

Very short leg - too short for any meals/snacks or entertainment.

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.

It was pretty straight forward, no glitches or hidden costs

Didn’t make it on the flight. Delayed then had to be rebooked, which in turn had me waiting at the airport for another 8 hours before next flight

All good……but luggage didn’t make it on the airplane. Had to wait 3 days. Was a bummer.

Small suitcase used for carryon the last time was refused by boarding crew this time. Appears to be at the discretion and mood of the person on the day. Flight was only half booked, there would have been no problem with space.

the check-in lady at ORD was extremely rude and unprofessional. very disappointed as it was supposed to be a celebration for my wife's birthday and it really put a damper on things. if i wanted to be treated like trash, i would have flown Economy! (as opposed to business class)

The whole plane smelled and felt old. The seats were very uncomfortable. Multiple delays. Extra fees.

The most uncomfortable flight I’ve ever been on. I’m only 5,4” and barely had enough room to exist, couldn’t even fully relax my shoulders. Not sure why they bother with snacks. Half a coke and a single cookie?? Wow. Purchasable food looked gross too. Remember when airlines used to treat you like a human being?

Departed Palm Springs over an hour late because there’s only one gate, and it has always delayed by the arriving and departing flight to Toronto and the arriving flight from Vancouver.

Extremely disappointing. My original Denver–Vancouver–Bangkok itinerary was cancelled due to a crewing issue. I was not proactively supported and had to drive back home after already reaching the airport. Communication was poor throughout, and attempts to contact customer service resulted in being on hold for nearly three hours without reaching anyone. Instead of being rebooked on the same direct routing the following day, I was rerouted onto a much longer itinerary via multiple cities and airlines, which resulted in arriving approximately 30 hours later than scheduled. At Denver airport, there was no visible Air Canada representative available to properly assist. Ground staff offered no real support beyond directing passengers to a phone number. There was no clear communication, no ownership, and no meaningful customer care during a major disruption. The final journey involved three flights instead of the original two, significantly increasing travel time and stress. Overall, the handling of the cancellation and lack of customer support was unacceptable. What could have been better? Clear communication during the cancellation Accessible customer service (phone support that actually answers) Proper in-person assistance at the airport Rebooking onto a comparable routing rather than a significantly longer one

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

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

Information on your arrival and departure airports