ORD - YLW

$145 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 4/9. 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
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Everything you should know

Cheapest round-trip
$318
WestJet
dom 5/3dom 5/10
ORD - YLW • 1 stop
Cheapest one-way
$145
Air Canada
qui 4/9
ORD - YLW • 1 stop
Top airlines
Cheapest • from $318 (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
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Insights
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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!
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

dom, mai 3 - dom, mai 10
WestJet Logo
5:30 pm - 11:50 pm
ORD
-
YLW
8h 20m
1 stop
WestJet Logo
6:05 am - 4:40 pm
YLW
-
ORD
8h 35m
1 stop
$318WestJet
qui, mai 14 - seg, mai 18
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
$322WestJet
dom, abr 26 - qui, abr 30
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
$323WestJet
sáb, abr 25 - qua, abr 29
Air Canada Logo
2:00 pm - 10:11 pm
ORD
-
YLW
10h 11m
1 stop
Air Canada Logo
5:20 am - 2:45 pm
YLW
-
ORD
7h 25m
1 stop
$342Air Canada
qui, mai 14 - seg, mai 18
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
$346WestJet
seg, mai 4 - qui, mai 7
Multiple Airlines Logo
6:00 am - 2:47 pm
ORD
-
YLW
10h 47m
1 stop
Multiple Airlines Logo
7:50 am - 4:40 pm
YLW
-
ORD
6h 50m
1 stop
$347Multiple Airlines
sáb, abr 25 - ter, abr 28
Air Canada Logo
2:00 pm - 10:11 pm
ORD
-
YLW
10h 11m
1 stop
Air Canada Logo
11:15 pm - 9:10 am
YLW
-
ORD
7h 55m
1 stop
$350Air Canada
qui, mai 14 - seg, mai 18
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
$354WestJet
qui, mai 14 - seg, mai 18
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
$356WestJet
sáb, abr 25 - ter, abr 28
Air Canada Logo
7:55 am - 10:53 pm
ORD
-
YLW
16h 58m
2 stops
Air Canada Logo
11:15 pm - 9:10 am
YLW
-
ORD
7h 55m
1 stop
$359Air Canada
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.

Which airlines provide the cheapest flights from Chicago to Kelowna?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago to Kelowna were found on WestJet ($318) and Air Canada ($342).

Good to know

Low seasonDecember
Cheapest flight$145
Best time to beat the crowds with an average 52% drop in price.
Most popular time to fly with an average 39% 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 $145 for a one-way ticket and $318 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 $588 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 12101 reviews
8.5Crew
7.0Entertainment
8.1Boarding
7.0Food
7.8Comfort
Airline reviews

The final trip home wasn’t as bad as the trip there. Even with the paid upgrade the comfort level was mediocre at best.

6.0 GoodAnonymous, Mar 2026
SEA - JFK
Read more Alaska Airlines reviews

The final trip home wasn’t as bad as the trip there. Even with the paid upgrade the comfort level was mediocre at best.

My trip to Seattle from Newark was uncomfortable and there was a maintenance issue that caused a delay which ended up with me being stuck at the Seattle airport on my birthday for almost 12 hrs. The ride itself was very bumpy due to turbulence. I u derstand as my first time flying this could have been normal but all the passengers around me said that this was not what flying is normally like. On my way home I was semi comfortable due to exhaustion and paying $200 in upgrades to have a “better” seat and experience

Flight delays were really annoying, but otherwise the experience was fine

Fine for a short flight. All went well. Snacks are lacking and I couldn’t hook up to wifi through the app, but it was fine.

Aircraft was freezing, cold air blowing on me the entire time and the individual fans were turned off.

The flight 2161 was cancelled after repeated delays; for some reason the crew and not the tower located in Billings, Montana made the call. A cancelled flight is not a big deal, it happens. It was very disappointing that upon cancelling the flight it was a free for all to get to the counter for rebooking. Priority seating and first class ticket holders should have been giving priority to get on the next available flight. Most would agree that the process of moving states away, w/a cat, is stressful. A cancelled flight, 90 minutes to rebook, no place to stay, medication that was to be refrigerated and trying to find a local pet friendly hotel significantly added to the stress. Had I been able to rebook (per priority boarding SOP) I could have called the place I had just checked out of as my room most likely was just as I'd left it, including with pet supplies (which also had to be repurchased). While waiting to rebook, many of us called Alaska Airlines 800 number hoping to get a new flight; the waiting time -- this is not a joke -- was eight (8) hours, which dropped to "just" two (2) hours about 45-minutes later. Due to the cancellation I had to spend $268.75 and I still have not been refunded for the change in ticket (first class to regular). Each time I've call, five times now, the wait time was absurd, or a message of call back is given. Hopefully visiting the airport and talking with an agent face to face will be the final chapter to this experience. Alaska has been my go to air travel for years, hopefully this trip was just a hiccup. A system that forces customer's to spend hours of their time (money) to get a just due refund is not a working system. I suggest Alaska Airlines hire more representatives to handle calls; time is more valuable than money, spending 90 minutes to rebook a flight, without the difference being automatic is absurd. There are things called computers, they do amazing things. Once the flight was cancelled, only three agents were working to rebook the PAX, This too was unacceptable. First class ticket holders pay for first-class service, this should include rebooking on flights that are cancelled. I recall a time when flights were cancelled the airline would offer a hotel should the next flight not be until the following day? I had no idea that was no longer SOP; many could return home, several of us could not. The agents were pleasant once the PAX had their turn to rebook, this was true down in baggage area as well. The flight out the next day was also what I'd come to find of Alaska Airlines.

I paid $129 to be upgraded to better seat only ti be completely ignored by flight attendants I think because I used the front restroom ???? I was dozing off and on but I was never once offered a beverage or snack but my seat mates were served numerous double vodkas. I want my money back. I tried to call Alaska Airlines complaints phone number and was told it was 2.5 hours to hold.

I paid for the $8 WiFi for the flight and it never worked. The crew told me it goes in and out and to keep trying. I didn’t get to watch the show I had planned to watch, bummer that I paid for the service. The person next to me said she has never been successful with in flight WiFi.

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.

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

Flight cancellations, delays, mass confusion and disorganization! That’s Air Canada for you, nothing new. I would have chosen a different airline if it were an option, and Air Canada continues to prove they don’t care about their customers.

The flight from SFO to YVR was delayed and my bag did not make it to my next flight from YVR to SYD. It took almost 3 days after I landed to get my bag and when I got it, it was filled with dust

Nothing specific. Cabin temperature was too high for some reason.

Over 40 years ago my AC return flight was canceled, during this last summer the same thing happened. AC denied everything Canadian like paying for accommodations and basic necessities. So why would I ever want to fly AC again? This last flight my wife took the return flight had problems and left late, so I guess they are getting better. However I have no faith in this airline so I drove to this last destination! I'll never fly AC again!!!

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

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

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

Information on your arrival and departure airports