ORD - YLW

$112 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 9/6. 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

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 (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

Wed, Sep 17 - Mon, Sep 22
WestJet Logo
5:30 pm - 9:49 pmORD-YLW
6h 19m1 stop
WestJet Logo
8:15 am - 4:43 pmYLW-ORD
6h 28m1 stop
$269WestJet
Find Deal
Wed, Sep 17 - Mon, Sep 22
WestJet Logo
5:30 pm - 10:00 amORD-YLW
18h 30m2 stops
WestJet Logo
8:15 am - 4:43 pmYLW-ORD
6h 28m1 stop
$306WestJet
Find Deal
Sat, Sep 13 - Sat, Sep 20
Alaska Airlines Logo
8:00 am - 1:57 pmORD-YLW
7h 57m1 stop
Alaska Airlines Logo
2:47 pm - 12:03 amYLW-ORD
7h 16m1 stop
$343Alaska Airlines
Find Deal
Sun, Sep 14 - Wed, Sep 17
 Logo
9:00 am - 10:00 amORD-YLW
27h 00m2 stops
 Logo
7:00 am - 4:43 pmYLW-ORD
7h 43m1 stop
Sat, Sep 13 - Sat, Sep 20
 Logo
5:30 pm - 11:39 pmORD-YLW
8h 09m1 stop
 Logo
5:55 am - 4:49 amYLW-ORD
20h 54m2 stops
Sat, Aug 30 - Sat, Sep 6
 Logo
11:21 am - 2:39 pmORD-YLW
29h 18m2 stops
 Logo
7:00 am - 4:43 pmYLW-ORD
7h 43m1 stop
Sun, Sep 14 - Wed, Sep 17
Alaska Airlines Logo
8:00 am - 1:57 pmORD-YLW
7h 57m1 stop
Alaska Airlines Logo
2:47 pm - 12:03 amYLW-ORD
7h 16m1 stop
$377Alaska Airlines
Find Deal
Wed, Sep 17 - Mon, Sep 22
Air Canada Logo
1:01 pm - 10:52 pmORD-YLW
11h 51m2 stops
Air Canada Logo
5:40 pm - 6:24 amYLW-ORD
10h 44m2 stops
$548Air Canada
Find Deal
Fri, Aug 29 - Mon, Sep 1
Air Canada Logo
3:40 pm - 10:48 pmORD-YLW
9h 08m1 stop
Air Canada Logo
8:35 pm - 3:00 pmYLW-ORD
16h 25m1 stop
$584Air Canada
Find Deal
Mon, Dec 29 - Mon, Jan 5
United Airlines Logo
10:00 pm - 5:38 pmORD-YLW
21h 38m2 stops
United Airlines Logo
10:00 am - 11:57 pmYLW-ORD
11h 57m2 stops
$639United Airlines
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 September, where tickets cost $386 (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 seasonDecember
Cheapest flight$112
Best time to beat the crowds but there is an average 77% increase in price.
Most popular time to fly with an average 62% 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 $112 for a one-way ticket and $269 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, Star Alliance, and SkyTeam 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.

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 10000 reviews
7.8Comfort
8.1Boarding
7.1Entertainment
8.5Crew
7.1Food
Airline reviews

If there were movies it would have made the flight much easier.

6.0 GoodAnonymous, Aug 2025JFK - SFO
Read more Alaska Airlines reviews

If there were movies it would have made the flight much easier.

We flew to Seattle on 7/21, right after the company wide problems the day before. We were delayed 3 hours but understood. We were grateful it wasn’t canceled. As a larger, disabled person, my son booked us in 1st class, row 1. That was fine. My problem occurred while trying to use the restroom. I had to back in and barely had room to move. I started into a silent panic attack where my breathing was affected. I made it back to my seat, shaken. I understand space is limited but something needs to be done. This was on the trip out. The return trip had 4-5 disabled passengers. I watched them struggle. This plane’s restroom was a “little “ bigger. It was a little easier compared to the first plane. That’s my opinion! The crews were fantastic on both flights!

Had to sit and wait to get off the plane for closeto a hour. My son also flying to a different destination that day also had like a 2.5 hr delay

Checking in very confusing compared to Hawaiian Airlines - much simpler! Front checking in at airport can improve. Hawaiian service always gives the extra mile, with a smile. Alaska can use and spread the Aloha Spirit. Mahalo nui loa Thank you 🤙

I was in the middle seat in the last row but that wasn’t their fault. It is why I rated the flight as mediocre, also the landing was a little rough. The good was really good. The self service luggage belt at SEATAC stopped working right when I reached it. I was literally placing my bag on the small belt when the main belt stopped. I understand that it wasn’t just Alaska but the entire side of the terminal. It took the agents about 20 minutes to arrive at a game plan and it certainly wasn’t flawless but they arranged for our luggage to be taken to the plane the old fashioned way by hand. Understandably, the plane was late in leaving. The flight took the proper amount of time and instead of arriving at OAK at 1:45, we got there at 2:30. I took my time getting to baggage claim because I knew it would be late if it was there at all. Sure enough it wasn’t but there was an agent there to greet me and inform me about my luggage. Long story longer, they delivered my luggage to where I was staying which was an hour away from the airport. Alaska has instituted a delivery type tracking system through my email that kept me informed of where my luggage was the whole time. WELL DONE!!

The flight was very smooth. The crew was very friendly.

Very nice as always. Not that it’s anyone’s fault really but for some reason the seat (16C) was really hard…. Not typical for your planes… dunno what or why… maybe it was just me ?, The flight was great otherwise

Flight attendant was rude when I advised her that the bathroom had no paper towels or tissue paper.

Crew was very friendly. Our bags showed up at the carousel within 20 minutes of arrival.

Flight was delayed and hour due to tire issue. First flight of the day, this issue should have been discovered prior to boarding.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

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.

Both flights are delayed so I rate the whole experience as mediocre.

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.

Aircraft had technical issues. After 3 hours of trying to resolve, flight was cancelled. Was booked on a flight leaving 12 hours after intended departure. Now on 4 flights instead of 2 and a day late to my destination.

Abandoned me in hallway in a wheelchair… which I asked for because I sprained my back. After waiting in the hallway, I decided to walk the rest of the way since someone respecting me up.. My experience with the united was totally the opposite. Wheelchair access, propped swift and save me a lot of grief. Air Canada totally disorganized.

Terrible confusion btw air Canada and United. Wasn’t able to change ticket because I had purchased on kayak. Rethinking booking tickets on this site, and will try to avoid United and aircanada going forward.

Conflicting information provided about baggage allowance. One screen said I had a carry on and another said I didnt.

Before final boarding, my husband and I — both seniors — were told that we could not bring our carry-on bags with us due to being in Zone 6. The staff took our bags with little explanation, stating it was policy. While we understand boarding procedures may vary by zone, the way we were spoken to was unnecessarily rude and dismissive. We felt disrespected and singled out, and the interaction left us deeply uncomfortable. As seniors, we expect to be treated with courtesy and dignity, especially during travel when accommodations and communication matter most. We hope you will look into this matter and ensure better training for staff in handling such situations with more empathy and professionalism.

Easy boarding and comfortable seating were plusses. Enjoyed the experience and good service from the captain and crew. Many thanks...!

Miserable staff as it was a late/delayed flight and crew wasn’t in the best spirits. Completely understood as neither was most of the passengers. Still unacceptable l.

It was a short flight, and no entertainment. That was not a problem for us, but there is no option for "not applicable". There was a bit of turbulence, so there was no food service.

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