HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kelowna

$191+ Cheap flights from Midway (MDW) to Kelowna (YLW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YLW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Kelowna with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Midway to Kelowna

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Kelowna (YLW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 14, 2025.

Round-trip from

$315
(Kiwi.com)

One-way from

$191
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$658
From Chicago Midway to Kelowna
Search Deals
One-way flight from Chicago Midway to Kelowna
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($108 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

Find flight deals from Midway to Kelowna

Cheapest flights from Midway to Kelowna
Explore the most affordable flight options available from Midway to Kelowna. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/179:00 amMDW - YLW
2 stops27h 04mMultiple Airlines
Mon 9/2211:30 pmYLW - MDW
1 stop14h 54mMultiple Airlines
Deal found 8/13$315
This FlightHub deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2710:31 amMDW - YLW
2 stops30h 08mWestJet
Sun 8/315:55 amYLW - MDW
2 stops25h 41mWestJet
Deal found 8/12$932
This WestJet deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2810:31 amMDW - YLW
2 stops13h 54mWestJet
Mon 10/66:30 pmYLW - MDW
2 stops13h 10mWestJet
Deal found 8/14$1,182
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/271:43 pmMDW - YLW
2 stops11h 31mDelta
Sun 8/315:55 amYLW - MDW
2 stops10h 42mDelta
Deal found 8/13$1,433

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Kelowna that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Kelowna that are best for you.

Fly from

Midway

Fly to

Kelowna

Route

Depart

Return

Price

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Wed 9/17

9:00 am-10:04 am

2 stops27h 04m

Kelowna

Mon 9/22

11:30 pm-4:24 pm

1 stop14h 54m

$315

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sat 1/24

2:00 pm-11:55 pm

2 stops11h 55m

Kelowna

Tue 2/3

5:20 am-9:46 pm

2 stops14h 26m

$514

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 1/29

4:15 pm-11:24 am

2 stops21h 09m

Kelowna

Tue 2/3

11:40 pm-3:20 pm

1 stop13h 40m

$632

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 1/29

10:35 am-10:00 pm

2 stops13h 25m

Kelowna

Tue 2/3

5:20 am-9:46 pm

2 stops14h 26m

$679

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Wed 8/27

10:31 am-2:39 pm

2 stops30h 08m

Kelowna

Sun 8/31

5:55 am-9:36 am

2 stops25h 41m

$932

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 8/28

10:31 am-10:25 pm

2 stops13h 54m

Kelowna

Mon 10/6

6:30 pm-9:40 am

2 stops13h 10m

$1,182

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Wed 8/27

1:43 pm-11:14 pm

2 stops11h 31m

Kelowna

Sun 8/31

5:55 am-6:37 pm

2 stops10h 42m

$1,433

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 10/13

10:56 pm-8:05 pm

3 stops23h 09m

$191

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sat 9/27

1:43 pm-11:39 pm

2 stops11h 56m

$198

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 8/28

10:31 am-11:34 pm

2 stops15h 03m

$443

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 17 results
1
2

Best time to book a flight from Midway to Kelowna

Have a flexible travel schedule? Discover the best time to fly to Kelowna from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Midway to Kelowna. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Kelowna from Chicago Midway?

    Kelowna (YLW) is the airport you will fly into if you book a flight from Chicago Midway to Kelowna. You should not have trouble finding flights to Kelowna from Chicago Midway; the airport handles an average of 0 inbound flights from Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights to the Kelowna airport from Chicago Midway. It is only a 7.0 mi journey from Kelowna (YLW) to Kelowna’s city center.

  • Can I find deals for flights from Midway to Kelowna that include hotel bookings?

    Yes. In addition to deals on Midway to Kelowna flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Kelowna?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Kelowna.

  • Can I find deals for business class flights from Midway to Kelowna?

    Yes. Cheapflights offers flight deals from Midway to Kelowna by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Kelowna?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Kelowna (average of $399). Flying from Chicago Midway Airport to Kelowna in December is currently the most expensive (average of $662). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Kelowna?

Book flights to Kelowna if you plan to visit one of these locations
Salmon Arm

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.