ORD - YLW

$117 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 11/27. 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
$343
Overall average: $1,098
WestJet
Fri 3/20Fri 3/27
ORD - YLW • 1 stop
Cheapest one-way
$117
Multiple Airlines
Thu 11/27
ORD - YLW • 2 stops
Top airlines
WestJet
Cheapest • from $343 (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 • 38% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Fri, Mar 20 - Fri, Mar 27
WestJet Logo
2:20 pm - 11:53 pmORD-YLW
11h 33m1 stop
WestJet Logo
5:20 am - 1:35 pmYLW-ORD
6h 15m1 stop
$343WestJet
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Tue, Apr 7 - Wed, Apr 8
Air Canada Logo
3:40 pm - 10:57 pmORD-YLW
9h 17m1 stop
Air Canada Logo
5:20 am - 2:43 pmYLW-ORD
7h 23m1 stop
$351Air Canada
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Sun, Mar 8 - Thu, Mar 12
Alaska Airlines Logo
7:45 am - 9:04 pmORD-YLW
15h 19m1 stop
Alaska Airlines Logo
1:20 pm - 11:59 pmYLW-ORD
8h 39m1 stop
$363Alaska Airlines
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Sun, Mar 8 - Thu, Mar 12
Multiple Airlines Logo
10:00 am - 9:48 pmORD-YLW
13h 48m2 stops
Multiple Airlines Logo
5:55 pm - 1:35 pmYLW-ORD
17h 40m1 stop
$422Multiple Airlines
Find Deal
Tue, Apr 7 - Wed, Apr 8
United Airlines Logo
10:40 am - 10:57 pmORD-YLW
14h 17m2 stops
United Airlines Logo
8:45 am - 4:50 pmYLW-ORD
6h 05m1 stop
$436United Airlines
Find Deal
Fri, Mar 20 - Sun, Mar 29
WestJet Logo
2:20 pm - 8:12 amORD-YLW
19h 52m1 stop
WestJet Logo
7:55 pm - 1:35 pmYLW-ORD
15h 40m1 stop
$437WestJet
Find Deal
Sun, Mar 22 - Fri, Mar 27
Delta Logo
7:30 am - 1:10 pmORD-YLW
7h 40m1 stop
Delta Logo
5:20 am - 1:35 pmYLW-ORD
6h 15m1 stop
$446Delta
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Tue, Apr 7 - Wed, Apr 8
United Airlines Logo
2:25 pm - 10:57 pmORD-YLW
10h 32m2 stops
United Airlines Logo
10:25 am - 9:13 pmYLW-ORD
8h 48m2 stops
$452United Airlines
Find Deal
Sun, Mar 22 - Sun, Mar 29
Multiple Airlines Logo
7:00 am - 1:10 pmORD-YLW
8h 10m1 stop
Multiple Airlines Logo
7:55 pm - 1:35 pmYLW-ORD
15h 40m1 stop
$517Multiple Airlines
Find Deal
Sat, Mar 21 - Fri, Mar 27
Delta Logo
7:30 am - 1:10 pmORD-YLW
7h 40m1 stop
Delta Logo
5:20 am - 1:35 pmYLW-ORD
6h 15m1 stop
$524Delta
Find Deal
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$117
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly with an average 72% 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 $117 for a one-way ticket and $343 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 $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 11214 reviews
8.1Boarding
7.1Food
8.5Crew
7.0Entertainment
7.8Comfort
Airline reviews

Overall the flight was on-time and plane ride very comfortable. The free snacks not so good - only a small bag of pretzels and no milk. I wanted milk. There was not entertainment on the plane unless I wanted to download their APP. But I would consider flying with them again and be more prepared on my part with food and entertainment.

10.0 ExcellentSara, Oct 2025JFK - SFO
Read more Alaska Airlines reviews

Overall the flight was on-time and plane ride very comfortable. The free snacks not so good - only a small bag of pretzels and no milk. I wanted milk. There was not entertainment on the plane unless I wanted to download their APP. But I would consider flying with them again and be more prepared on my part with food and entertainment.

Kayak I had marked one carry on, one checked bag. Yet when it completed the purchase marked it as no carry on. Fail on kayaks side! Then extended flight delayed due to computer issues. Crew of the plane did awesome but fail on both kayak and alaskan

In both halves of the trip (going and returning) there were problems. Not exactly Alaska's fault, but still really difficult. Outgoing flight was canceled and rebooked twice due to a total ground stop of all Alaska's flights. This required me to change airports with minimal notice and I almost missed my flight transferring to the other airport (which was roughly an hour and a half away). On the return, the first leg was delayed by an hour, and the second leg was delayed by nearly 3 hours. This was a rough set of flights and the communication about all of these changes was minimal. Crew did their best however, so no fault there. Other thing to remember is there is no food on Alaska flights unless you pre-order. Take that into account when you choose airlines.

Its bumpy but I can say its safe flight ,Thanks Alaska airline for bringing me in my destination😊.

Late. Too long a flight for a 737. 0.5 oz of pretzels for a 5+ hour flight at dinner time. One step above Ryan Air/ several below Delta.

Waiting 2 hours after landing to arrive at a gate was ridiculous.

Almost 3 hr delay in Settle with very little information available to passengers. They boarded the plane and we waited for a long time inside the plane as well.

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

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.

The friendliest flight attendants at flight 2276 from Portland to YVR August 3

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

The flight attendants were rude. Seemed like they didn’t want to be there. Except for one girl that was really nice. Seats are sooooo uncomfortable. They give you a piece of paper and a thin cushion for a pillow and blanket that does nothing. Airlines have gone way downhill, especially United international flights. Food was disguting. Definitely flying ANA next time.

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

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.

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.

Fair. What's the point of partnering with United if we cannot use the lounge. My wife is a frequent flier with United but we were refused access to Air Canada lounge

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

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.

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

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