ORD - YLW

$99 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 3/2. 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
$228
WestJet
Fri 4/10Fri 4/17
ORD - YLW • 1 stop
Cheapest one-way
$99
Air Canada
Mon 3/2
ORD - YLW • 1 stop
Top airlines
WestJet
Cheapest • from $228 (round-trip)
Alaska Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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

Fri, Apr 10 - Fri, Apr 17
WestJet Logo
2:20 pm - 7:08 pm
ORD
-
YLW
6h 48m
1 stop
WestJet Logo
5:20 am - 1:35 pm
YLW
-
ORD
6h 15m
1 stop
$228WestJet
Tue, Mar 3 - Wed, Mar 4
Air Canada Logo
3:35 pm - 11:13 pm
ORD
-
YLW
9h 38m
1 stop
Air Canada Logo
5:20 am - 2:41 pm
YLW
-
ORD
7h 21m
1 stop
$239Air Canada
Tue, Mar 3 - Wed, Mar 4
Air Canada Logo
3:55 pm - 10:20 pm
ORD
-
YLW
8h 25m
1 stop
Air Canada Logo
11:25 pm - 9:13 am
YLW
-
ORD
7h 48m
1 stop
$251Air Canada
Tue, Mar 3 - Wed, Mar 4
Air Canada Logo
8:00 am - 7:59 pm
ORD
-
YLW
13h 59m
2 stops
Air Canada Logo
11:25 pm - 9:13 am
YLW
-
ORD
7h 48m
1 stop
$257Air Canada
Tue, Mar 3 - Wed, Mar 4
Air Canada Logo
8:00 am - 11:13 pm
ORD
-
YLW
17h 13m
2 stops
Air Canada Logo
5:20 am - 2:41 pm
YLW
-
ORD
7h 21m
1 stop
$274Air Canada
Tue, Mar 3 - Wed, Mar 4
Air Canada Logo
8:00 am - 7:59 pm
ORD
-
YLW
13h 59m
2 stops
Air Canada Logo
6:15 pm - 3:10 pm
YLW
-
ORD
18h 55m
2 stops
$281Air Canada
Mon, Mar 2 - Fri, Mar 6
WestJet Logo
2:20 pm - 7:08 pm
ORD
-
YLW
6h 48m
1 stop
WestJet Logo
5:20 am - 1:35 pm
YLW
-
ORD
6h 15m
1 stop
$315WestJet
Mon, Mar 9 - Sat, Mar 14
Multiple Airlines Logo
2:20 pm - 7:08 pm
ORD
-
YLW
6h 48m
1 stop
Multiple Airlines Logo
7:35 pm - 1:35 pm
YLW
-
ORD
40h 00m
2 stops
$326Multiple Airlines
Fri, Apr 10 - Fri, Apr 17
Multiple Airlines Logo
2:20 pm - 7:08 pm
ORD
-
YLW
6h 48m
1 stop
Multiple Airlines Logo
7:35 pm - 10:44 am
YLW
-
ORD
13h 09m
2 stops
$334Multiple Airlines
Thu, Feb 26 - Sun, Mar 1
Air Canada Logo
9:15 am - 8:13 am
ORD
-
YLW
24h 58m
2 stops
Air Canada Logo
11:25 pm - 9:50 am
YLW
-
ORD
8h 25m
1 stop
$357Air 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 ($228) and Air Canada ($239).

Good to know

Low seasonDecember
Cheapest flight$99
Best time to beat the crowds with an average 48% drop in price.
Most popular time to fly with an average 49% 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 $99 for a one-way ticket and $228 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 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 $947 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 11825 reviews
7.1Food
8.1Boarding
7.0Entertainment
8.5Crew
7.8Comfort
Airline reviews

I think Alaska should start including free meals on these longer trips.

6.0 GoodAnonymous, Feb 2026
SEA - DCA
Read more Alaska Airlines reviews

I think Alaska should start including free meals on these longer trips.

Wheelchair assistance was excellent. I had a saver fare, but was given a seat in Premium. So very nice!! Extra legroom, complimentary beer. The flight crew was very nice and efficient. The gate agent in Seattle double checked to make sure I was able to board the plane all right while using my cane. I boarded first. So considerate! The flight was smooth, and right on time.

Wheelchair assistant was on the spot, and very helpful. Gate agent was kind, and made sure I boarded the plane without having to try to hurry with my painful hip. My seat was so comfortable, 20A. I am tall, 5'9 and I need to stretch out my legs due to chronic nerve pain in my back that runs down my right leg, in addition to the bursitis in my right hip. Alaska air has the best economy seating in the market. So much room for legs, elbows, etc. When I arrived in SEA, the next Wheelchair was waiting to take me to the next gate. Great communication.

I had to cancel my trip due to health reasons three days after making the reservation. I was stunned to find out that the ticket was not able to be credited for future travel. $734 loss. Not happy that this was not my experience with Southwest Airlines. I will stick with SW in the future. Boo Alaskan Air and Kayak.

Due to plane delays on both legs of my flight home, I had to be rerouted from Santa Rosa to Las Vegas on Skywest and then to DCA on American. SkyWest airlines sat on runway in Las Vegas for 20 minutes waiting for gate to clear. My boarding pass for American that I was given by Alaska was incomplete and the Las Vegas airport lacked signage and departure boards. I barely made my flight bc it was so confusing. American Airlines has a much better wireless connection. I’ll never fly Alaska again. It clearly has problems.

Great. I did have a little issue getting into the Lounge, which is likely more an American Airlines issue. I did not carry my physical AAdvantage Executive credit card with me on this trip, which Admirals Club membership is a part of the benefits of having this card. The instructions on the AA website and the Citi cards website make it seem like you don't need the physical card, as both sites state you can enter with your boarding pass and driver's license. But both lounges said you were required to present the physical card (and not the digital version, via Apple Pay), as only the physical card says "Admirals Club" on the back.I also do not have a physical Admirals Club membership card, so while both lounges eventually let me in, both denied me entrance initially for this reason.

I paid for wifi and it never worked... it was miserable. I couldn't access my shared files to work on the plane, it didn't work on my phone. I paid for nothing but frustration and continual refreshing, hoping it would work

We left about 30 minutes late due to ramp issues. It did not impact me, but I know others on the flight had very tight connections to Maui.

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.

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

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!!!

Great check in process in LA and good service The check in process as well as at the gate is way better in the US versus canada 🇨🇦

Boarding was so so after zone 3 was called all other zones went in

For goodness sake, board from the back of the plane to the front and assign overhead space. It would fix everything. Seriously.

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