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Kelowna

$140+ 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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YLW
Oct 31 — Nov 71
Fri 10/31
Fri 11/7
1 adult, Economy
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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 October 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$973
(Mytrip)

One-way from

$140
(Kiwi.com)

Popular in

December

Cheapest in

March
Provider with most accurate pricing for Chicago Midway-Kelowna flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Kelowna flights.
Search Deals
From Chicago Midway to Kelowna
Search Deals
One-way flight from Chicago Midway to Kelowna
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($90 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($25 potential savings vs. average RT price).
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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 October 1, 2025.

This Mytrip deal was found by Cheapflights users on 9/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/169:20 amMDW - YLW
3 stops16h 19mWestJet
Fri 10/1710:00 amYLW - MDW
3 stops22h 30mWestJet
Deal found 9/28$973
This WestJet deal was found by Cheapflights users on 9/30. 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.
Fri 11/149:41 amMDW - YLW
2 stops10h 49mWestJet
Fri 11/216:35 pmYLW - MDW
2 stops13h 18mWestJet
Deal found 9/30$1,023

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 October 1, 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

Thu 10/16

9:20 am-11:39 pm

3 stops16h 19m

Kelowna

Fri 10/17

10:00 am-10:30 am

3 stops22h 30m

$973

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 11/14

9:41 am-6:30 pm

2 stops10h 49m

Kelowna

Fri 11/21

6:35 pm-9:53 am

2 stops13h 18m

$1,023

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 10/27

10:56 pm-2:27 pm

2 stops17h 31m

$140

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 10/13

5:28 pm-1:56 pm

3 stops46h 28m

$205

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 11/13

11:00 am-11:55 pm

3 stops14h 55m

$252

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sat 11/15

1:47 pm-11:24 am

3 stops23h 37m

$270

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sat 11/15

1:47 pm-11:03 am

2 stops23h 16m

$270

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 11/13

9:41 am-6:30 pm

2 stops10h 49m

$422

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 10/27

9:20 am-6:30 pm

2 stops11h 10m

$443

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sat 2/21

6:45 pm-2:31 pm

2 stops21h 46m

$494

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/1

Showing 1-10 of 11 results
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Compare providers for flights from Midway to Kelowna

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Kelowna in October.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Kelowna flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Kelowna flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Kelowna flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Kelowna flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Kelowna flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

  • How long is the flight from Chicago Midway Airport to Kelowna?

    Airlines like WestJet fly from Chicago Midway Airport to Kelowna in about 16h 19m. The time it takes to get you to your destination can typically vary by up to . Chicago Midway Airport and Kelowna are separated by a distance of 1607 mi.

  • 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?

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