A spacious airport terminal with high ceilings, check-in counters, and a Starbucks coffee shop.

CA $215 Cheap Flights from Kelowna (YLW) to Chicago (ORD)

View CA $215 flight on Sat, Oct 24, 2026Opens in a new window

Popular airlines from Kelowna Intl. Airport (YLW) to Chicago O'Hare International Airport (ORD)

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap flights from Kelowna (YLW) to Chicago (ORD)

Prices were available within the past 7 days and start at CA $215 for one-way flights and CA $368 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Thu, Nov 19 - Sat, Nov 28
YLW
Kelowna
ORD
Chicago
CA $368 Roundtrip, found 7 hours ago
CA $368
Roundtrip
found 7 hours ago
Select Air Canada flight, departing Thu, Nov 19 from Kelowna to Chicago, returning Sat, Nov 28, priced at CA $368 found 7 hours ago
Air Canada
Sat, Oct 31 - Tue, Nov 3
YLW
Kelowna
ORD
Chicago
CA $369 Roundtrip, found 2 days ago
CA $369
Roundtrip
found 2 days ago
Select Air Canada flight, departing Sat, Oct 31 from Kelowna to Chicago, returning Tue, Nov 3, priced at CA $369 found 2 days ago
Air Canada
Sun, Oct 11 - Sat, Oct 17
YLW
Kelowna
ORD
Chicago
CA $373 Roundtrip, found 3 days ago
CA $373
Roundtrip
found 3 days ago
Select Air Canada flight, departing Sun, Oct 11 from Kelowna to Chicago, returning Sat, Oct 17, priced at CA $373 found 3 days ago
Alaska Airlines
Wed, Sep 30 - Wed, Oct 14
YLW
Kelowna
ORD
Chicago
CA $376 Roundtrip, found 1 day ago
CA $376
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Wed, Sep 30 from Kelowna to Chicago, returning Wed, Oct 14, priced at CA $376 found 1 day ago
Air Canada
Mon, Nov 30 - Sat, Dec 5
YLW
Kelowna
ORD
Chicago
CA $379 Roundtrip, found 1 day ago
CA $379
Roundtrip
found 1 day ago
Select Air Canada flight, departing Mon, Nov 30 from Kelowna to Chicago, returning Sat, Dec 5, priced at CA $379 found 1 day ago
Air Canada
Sat, Oct 3 - Tue, Oct 6
YLW
Kelowna
ORD
Chicago
CA $380 Roundtrip, found 10 hours ago
CA $380
Roundtrip
found 10 hours ago
Select Air Canada flight, departing Sat, Oct 3 from Kelowna to Chicago, returning Tue, Oct 6, priced at CA $380 found 10 hours ago
Air Canada
Fri, Oct 2 - Sat, Oct 3
YLW
Kelowna
ORD
Chicago
CA $384 Roundtrip, found 4 days ago
CA $384
Roundtrip
found 4 days ago
Select Air Canada flight, departing Fri, Oct 2 from Kelowna to Chicago, returning Sat, Oct 3, priced at CA $384 found 4 days ago
WestJet
Sun, Oct 11 - Thu, Oct 15
YLW
Kelowna
ORD
Chicago
CA $389 Roundtrip, found 12 hours ago
CA $389
Roundtrip
found 12 hours ago
Select WestJet flight, departing Sun, Oct 11 from Kelowna to Chicago, returning Thu, Oct 15, priced at CA $389 found 12 hours ago
Delta
Sun, Oct 11 - Tue, Oct 13
YLW
Kelowna
ORD
Chicago
CA $467 Roundtrip, found 12 hours ago
CA $467
Roundtrip
found 12 hours ago
Select Delta flight, departing Sun, Oct 11 from Kelowna to Chicago, returning Tue, Oct 13, priced at CA $467 found 12 hours ago
United
Thu, Nov 19 - Sat, Nov 28
YLW
Kelowna
ORD
Chicago
CA $494 Roundtrip, found 7 hours ago
CA $494
Roundtrip
found 7 hours ago
Select United flight, departing Thu, Nov 19 from Kelowna to Chicago, returning Sat, Nov 28, priced at CA $494 found 7 hours ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city centre is 16 minutes. Flights from CA $1,771
MDW
Midway Intl.
Closest
Average driving time to city centre16 min
Flights from CA $1,771

Find the cheapest month to fly from Kelowna (YLW) to Chicago (ORD)

February is typically the cheapest month to fly

From CA $279 - CA $939 per traveller.

Frequently asked questions

How much does a flight from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from CA $215 and cheap return flights from CA $368 YLW to ORD with Expedia. One-way flights typically cost between CA$261 and CA$1118, and return flights often range between CA$727 and CA$2330. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when YLW to ORD ticket fares go up or down.
What is the cheapest month to fly from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you're looking for the cheapest time to fly from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.), September is typically your best bet. You can expect average return fares around CA$554 during this month. Other budget-friendly months for this route include May and August.
Which airlines fly direct from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Enter YLW to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Kelowna, BC (YLW) to Chicago, IL (ORD)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are approximately 21 connecting flights per day from Kelowna International (YLW) to O'Hare Intl. (ORD). Some common connection points include Vancouver Intl. (YVR), Seattle - Tacoma Intl. (SEA), and Calgary Intl. (YYC).
What is the earliest flight from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically departs around 5:05 AM. This route is a seasonal service, active only in June, and is operated by airlines such as WestJet and Delta. An early departure like this can be great for maximizing your time in Chicago, allowing you to arrive with a full day ahead. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You'll typically find the most flights from Kelowna International (YLW) to O'Hare Intl. (ORD) on a Wednesday, with around 27 flights available. This gives you a good selection of options for your travel plans. Major airlines on this route include Air Canada, WestJet, and Alaska Airlines. There are notably more flight options on Wednesdays compared to other days of the week, so planning your trip for a Wednesday could give you more flexibility.
What are the most popular departure times for flights from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Kelowna International (YLW) to O'Hare Intl. (ORD) are in the early morning, from 3am to 6am. Many major carriers, including Air Canada and WestJet, offer flights during this window. Many travelers prefer these early morning flights to get a head start on their journey and arrive at their destination earlier in the day.
How long does it take to fly from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are no nonstop flights from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.). For flights with one stop, you can expect the journey to take around 9 hours 51 minutes. If your travel involves two or more stops, the total flight time will typically be longer, averaging about 13 hours 49 minutes. The distance between Kelowna and Chicago is approximately 2,567 kilometres. Keep in mind that actual flight times can vary due to factors like layover duration, routing, and weather conditions.
Can you fly business or first class from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Yes, you can fly business class or first class between Kelowna, BC (YLW) and Chicago, IL (ORD).You can fly business class with Air Canada.First class cabins are available on Alaska Airlines.
How do I earn miles on a Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago, IL (ORD) from Kelowna, BC (YLW)?
If you're planning to travel to Chicago from Kelowna International (YLW), you can fly directly into O'Hare Intl. (ORD). Some flights may connect through major hubs like Vancouver Intl. (YVR), Calgary Intl. (YYC), or Pearson Intl. (YYZ) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Kelowna Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, Alaska Airlines, American Airlines, Delta, Porter Airlines, United, WestJet
Roundtrip price
CA $367
Distance
2551 km

Book with confidence

Kelowna to Chicago Flights

The easy way to book your flights from Kelowna to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Kelowna whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to O'Hare Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Kelowna to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Kelowna Intl., YLW to O'Hare Intl., ORD 

Sort your search results by price to find great deals on your flight from Kelowna to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Kelowna currently is just CA $368 rising to CA $494.  

Here are more money-saving tips: 

  • Fly in November when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Kelowna 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

Kelowna to Chicago Flights

Explore a world of travel with Expedia

*Available to Expedia members.