CA $513 Cheap Flights from Kelowna (YLW) to Chicago (MDW)

View CA $513 flight on Fri, Aug 28, 2026Opens in a new window

Popular airlines from Kelowna Intl. Airport (YLW) to Chicago Midway Airport (MDW)

  • 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 (MDW)

Prices were available within the past 7 days and start at CA $513 for one-way flights and CA $985 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Fri, Aug 7 - Mon, Aug 10
YLW
Kelowna
MDW
Chicago
CA $985 Roundtrip, found 4 days ago
CA $985
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Fri, Aug 7 from Kelowna to Chicago, returning Mon, Aug 10, priced at CA $985 found 4 days ago
Porter Airlines
Mon, Jul 20 - Thu, Jul 30
YLW
Kelowna
MDW
Chicago
CA $1,001 Roundtrip, found 3 days ago
CA $1,001
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Mon, Jul 20 from Kelowna to Chicago, returning Thu, Jul 30, priced at CA $1,001 found 3 days ago
Porter Airlines
Fri, Jul 10 - Mon, Jul 13
YLW
Kelowna
MDW
Chicago
CA $1,021 Roundtrip, found 5 days ago
CA $1,021
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Fri, Jul 10 from Kelowna to Chicago, returning Mon, Jul 13, priced at CA $1,021 found 5 days ago
Porter Airlines
Fri, Jul 17 - Thu, Jul 30
YLW
Kelowna
MDW
Chicago
CA $1,052 Roundtrip, found 3 days ago
CA $1,052
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Fri, Jul 17 from Kelowna to Chicago, returning Thu, Jul 30, priced at CA $1,052 found 3 days ago
Porter Airlines
Fri, Aug 7 - Mon, Aug 10
YLW
Kelowna
MDW
Chicago
CA $1,094 Roundtrip, found 4 days ago
CA $1,094
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Fri, Aug 7 from Kelowna to Chicago, returning Mon, Aug 10, priced at CA $1,094 found 4 days ago
WestJet
Fri, Jul 10 - Mon, Jul 13
YLW
Kelowna
MDW
Chicago
CA $1,152 Roundtrip, found 5 days ago
CA $1,152
Roundtrip
found 5 days ago
Select WestJet flight, departing Fri, Jul 10 from Kelowna to Chicago, returning Mon, Jul 13, priced at CA $1,152 found 5 days ago
WestJet
Fri, Jul 17 - Thu, Jul 30
YLW
Kelowna
MDW
Chicago
CA $1,157 Roundtrip, found 3 days ago
CA $1,157
Roundtrip
found 3 days ago
Select WestJet flight, departing Fri, Jul 17 from Kelowna to Chicago, returning Thu, Jul 30, priced at CA $1,157 found 3 days ago
WestJet
Fri, Jul 10 - Mon, Jul 13
YLW
Kelowna
MDW
Chicago
CA $1,195 Roundtrip, found 5 days ago
CA $1,195
Roundtrip
found 5 days ago
Select WestJet flight, departing Fri, Jul 10 from Kelowna to Chicago, returning Mon, Jul 13, priced at CA $1,195 found 5 days ago
WestJet
Fri, Jul 17 - Thu, Jul 30
YLW
Kelowna
MDW
Chicago
CA $1,201 Roundtrip, found 3 days ago
CA $1,201
Roundtrip
found 3 days ago
Select WestJet flight, departing Fri, Jul 17 from Kelowna to Chicago, returning Thu, Jul 30, priced at CA $1,201 found 3 days ago
Porter Airlines
Fri, Jul 10 - Mon, Jul 13
YLW
Kelowna
MDW
Chicago
CA $1,208 Roundtrip, found 5 days ago
CA $1,208
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Fri, Jul 10 from Kelowna to Chicago, returning Mon, Jul 13, priced at CA $1,208 found 5 days ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from CA $596
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from CA $596

Frequently asked questions

Which airlines fly direct from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter YLW to MDW 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 (MDW-Midway Intl.)?
To find a cheap flight from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (MDW-Midway 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-Kelowna Intl.) to Chicago, IL (MDW-Midway Intl.)?
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 (MDW-Midway Intl.)?
There are approximately 6 connecting flights per day from Kelowna International (YLW) to Midway Intl. (MDW). Some common connection points include Calgary Intl. (YYC), Vancouver Intl. (YVR), and Pearson Intl. (YYZ).
What is the earliest flight from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (MDW-Midway Intl.) typically departs at approximately 5:55 AM local time. This service is operated by WestJet and Delta. This is a seasonal service active in August. An early departure like this can help maximize your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
How long does it take to fly from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (MDW-Midway Intl.)?
Flying from YLW to MDW with a connection usually takes about 16 hours, traveling roughly 1,609 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (MDW-Midway Intl.)?
Select the "Business class" and "First class" filters when looking for YLW to MDW flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (MDW-Midway 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 from Kelowna International (YLW)?
When traveling from Kelowna International (YLW) to Chicago, you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW). Some flights may connect through major hubs like Vancouver Intl. (YVR), Calgary Intl. (YYC), 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 (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (MDW-Midway 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 (MDW-Midway Intl.) flight and hotel package?
Securing a Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (MDW-Midway 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 (MDW-Midway Intl.)?
If you booked your Kelowna, BC (YLW-Kelowna Intl.) to Chicago, IL (MDW-Midway 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
Midway Intl.
Roundtrip price
CA $984
Distance
2573 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 Midway 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 Midway Intl., MDW 

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 $985 rising to CA $1,208.  

Here are more money-saving tips: 

  • Fly in August 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.