ORD - YLW

$165 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 6/13. 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.
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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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Flights Deals

Cheap Flights from Chicago to Kelowna

 
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.

Recent round-trip flight deals from Chicago to Kelowna

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Kelowna.
Discover the best prices for you by selecting your travel dates on KAYAK.
Air Canada Logo
8:48 am - 4:57 pmORD-YLW
10h 09m1 stop
Air Canada Logo
11:30 pm - 9:09 amYLW-ORD
7h 39m1 stop
$282Air Canada
Find Deal
Sat, Jun 14 - Sat, Jun 21
Air Canada Logo
7:35 pm - 9:12 amORD-YLW
15h 37m1 stop
Air Canada Logo
11:30 pm - 9:09 amYLW-ORD
7h 39m1 stop
$284Air Canada
Find Deal
Sat, Jun 14 - Sat, Jun 21
 Logo
11:50 am - 10:55 amORD-YLW
25h 05m2 stops
 Logo
11:30 pm - 9:09 amYLW-ORD
7h 39m1 stop
Fri, Jun 13 - Fri, Jun 20
 Logo
11:50 am - 10:55 amORD-YLW
25h 05m2 stops
 Logo
11:30 pm - 9:09 amYLW-ORD
7h 39m1 stop
Fri, Jun 13 - Fri, Jun 20
United Airlines Logo
5:02 am - 10:32 pmORD-YLW
19h 30m2 stops
United Airlines Logo
5:45 am - 11:13 pmYLW-ORD
15h 28m2 stops
$327United Airlines
Find Deal
Sat, Jun 14 - Sat, Jun 21
United Airlines Logo
7:10 am - 10:32 pmORD-YLW
17h 22m2 stops
United Airlines Logo
5:45 am - 10:41 pmYLW-ORD
14h 56m2 stops
$342United Airlines
Find Deal
Sat, Jun 14 - Sat, Jun 21
WestJet Logo
5:30 pm - 11:49 pmORD-YLW
8h 19m1 stop
WestJet Logo
7:00 am - 4:44 pmYLW-ORD
7h 44m1 stop
$363WestJet
Find Deal
Sat, Aug 9 - Tue, Aug 12
WestJet Logo
5:30 pm - 11:49 pmORD-YLW
8h 19m1 stop
WestJet Logo
7:00 am - 4:44 pmYLW-ORD
7h 44m1 stop
$384WestJet
Find Deal
Sat, Aug 9 - Sat, Aug 16
Alaska Airlines Logo
6:00 am - 1:46 pmORD-YLW
9h 46m1 stop
Alaska Airlines Logo
2:36 pm - 11:59 pmYLW-ORD
7h 23m1 stop
$438Alaska Airlines
Find Deal
Thu, Jun 26 - Fri, Jun 27
Alaska Airlines Logo
7:00 am - 1:46 pmORD-YLW
32h 46m2 stops
Alaska Airlines Logo
2:36 pm - 6:18 pmYLW-ORD
25h 42m2 stops
$514Alaska Airlines
Find Deal
Sat, Aug 9 - Tue, Aug 12
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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 May, where tickets cost $340 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $1,202 and $1,099 respectively.

Good to know

Low seasonAugust
High seasonMarch
Cheapest flight$165
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly with an average 67% 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 $165 for a one-way ticket and $282 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 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.

Top 4 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 9968 reviews
7.1Entertainment
8.5Crew
8.2Boarding
7.1Food
7.9Comfort
Airline reviews

It was all great all around. Will travel with Alaska next trip.

10.0 ExcellentLoyola, Apr 2025BOS - SEA
Read more Alaska Airlines reviews

It was all great all around. Will travel with Alaska next trip.

I got the last seat on the plane, in the back in the corner against the window, and I paid a competitive price for my ticket several weeks before the flight.

Everything was good. However, the selections of movies and TV shows were boring and unexciting. It was disappointing.

Long delay before boarding. By the time I was informed of the delay I was already at the gate.

There was no seating at the gate, no where to charge your devices, super crowded. Boarding in group F meant all luggage space was taken when it was time for me to board. The boarding crew was short with everyone and seemed irritated. The luggage space was insufficient, the seat was too small for me (6'4") and very uncomfortable trip. I was in a middle seat between a person snoring the whole trip and a person with very strong body odor. The flight crew was terse and unfriendly, seemed irritated and impatient. Yelled a lot at people with earbuds in, understandable. Finally, we arrived 10 minutes early, only to sit on the tarmac for 20 minutes and wait for a gate. Worst flight experience I've had in years.

I made a mistake. Read what I wrote in the flight from Dulles to SEA. The negative experience was from SEA to BOI. Total garbage. Wont do it again.

Flight 351 SEA to BOI was terrible. We got to cruising altitude and I needed to use the restroom but the fasten seatbelt sign never came off. There was no turbulence and I'd felt the plane level off so I stood up to use the restroom about 15 minutes after we leveled off. The stewardess went over the intercom and said I needed to be seated because the captain hadn't turned off the fasten seatbelt sign....Which... Fair.... But not five minutes later she went and used the bathroom. Felt very unprofessional to leave a paying customer with a burning urethra for the entire flight and bark at them to sit down and still use the bathroom yourself. They never did turn off the seatbelt sign.

For longer trips, snacks are puny, boring and don’t have ANY nutritional value.

One of the worst check-in experiences ever. Apparently, we were overweight and had to completely repack. They tried to charge us an extra $35 per bag on top of the standard checked baggage fee we had already paid in advance. Surprisingly, we managed to fit everything into our carry-ons and stayed under their precious 50-pound limit. (By the way, 23 kg is actually 50.7 lbs, so we couldn’t even go slightly over 50 according to the very unfriendly agent.)

OUr pilot was very good and also a good landing in a very gusting Phoenix. Most important.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

My husband required a wheelchair to get to the airplane and the service he received was exemplary. Thank you.

WestJet was able to re-book us to the next available flight at no charge when air traffic controller staffing shortage delayed our inbound flight

Plane changed to one with no entertainment system or ability to serve hot meals

I am a tall woman and could not move my legs enough to reach down under the seat in front of me to retrieve anything I put down there. I sat in both aisle and window seats and felt extremely cramped. In the aisle seat, if the stewardess was heavy, it was impossible to pass, and she would knock my arm shoulder and thigh every time she went by. If I can avoid it, I will not be flying this airline again.

We never had an experience they canceled the flight and they did not offer us an alternative flight. I had to book one on my own expense. They offered us food voucher and we could not use them at the airport it kept saying not attached to an existing flight. The people at the counter were rude and cold and they did not care about our situation

Get our, as a group, skis on time to their destination. Have more attendants checking people in. There was only one. The line was a block long :( . Also flight change with 5-hour delay

First flight out in the morning is often the best chance of running on time. Not in this case, which unfortunately is now what passengers can expect as what is common. - If you are late for a flight, too bad for you. - If West Jet is late, too bad for you. - Bags don't make it? Too bad for you. - Flight change by 1+ days, too bad for you Prices continue to increase, while customer service nosedives. This is backwards and in any other develop country would be considered unacceptable - except for Canada. Too bad for us.

Horrible. I checked out myself that it seems that I can have a free carry-on. But they ask me to pay $75 when we are nearly boarding. It was tricky during check out that make you mistake that you can have a carry-on beside your personal item. Also they ask $75 in the airport instead of $35 during checkout. So the whole process is designed to make you this mistake

Westjet has been absolutely terrible! Flights continually cancelled. Took 4 days to get home. Would have been 5, but we booked last flight with another airline after our Westjet flight was cancelled. Even pilot on original flight looked frustrated! Funny how they say cancelation is weather related, but they still have more than 1 other flight leaving to same destination on same day, but of course those are all full. This happened more than once on this trip. Two weather related cancelations and 1 mechanical. Not sure if the last flight even went ahead. Felt so sorry for families with kids and babies, and the older travellers. Felt like we lived out of suitcases and airports for days - SO RIDICULOUS! Next to no help from Westjet staff at airports, but it appears there is nothing they can help you with. Westjet has made it that they are unreachable when you need them! People were getting extremely frustrated, and rightfully so. Additional costs to us really added up, but Westjet literally DOESN'T CARE! Final straw was when we had to pay $1280 on a different airline (economy) trying to get home after another cancelled flight. Westjet will be refunding us a whole $140! Can't believe how this airline operates. We will never, ever use them again!

The only thing I didn’t like was how far away the gate was. I would have requested a wheelchair had I known.

All was good except for the seats, not very comfy.

2.5 hour delay sitting in the plane on the tarmac, you tell me how the experience was

This flight didn't happen for me because of overbooking.

Poor air traffic controller staffing led to a 50%reduction on flights so we got to wait 4 hrs for our flight! Very disorganized at the gate Poor communication with customers

It was delayed by almost 90 minutes and that messed up our plans but it was beyond UA’s control that is what we heard

Everything was simple and easy. The lady at the gate was super friendly, I wish I had her name to share. She's a little older, dark-haired. You can tell she likes her job and would be a great influence on any young people training with her.

Crammed in like cattle waited 30 mins for late connecting flight (flight didn’t wait for me for me when I missed my connection at 2 different airports on outward journey)

PDX staff was great and we arrived on time in YVR.

They announced before boarding that the flight was full and there would be limited space in the overhead bins and you could check in for free. We did and after we boarded the plane found it was not full and there was plenty of space in the overhead bins. I’m not sure why they made this announcement.

They are a great airline, and i enjoying flying with them. However my experience with booking through Kayak was a horrible experience. With all the restrictions and glitches of website. My entire bookings by kayak was wrong. And there was no possible way of fixing anything with them, because they hand over responsibility to the airline after purchase is made. Will not be booking through Kayak again and will inform my family and friends not to as well.

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

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