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Kelowna

$151+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YLW
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$288
(Kiwi.com)

One-way from

$151
(Kiwi.com)

Popular in

October

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. 29% potential increase in price ($222 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 13% potential price decrease ($61 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 November 13, 2025.

This Mytrip deal was found by Cheapflights users on 11/11. 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.
Fri 12/2611:00 amMDW - YLW
3 stops35h 41mMultiple Airlines
Fri 1/27:55 pmYLW - MDW
3 stops17h 25mMultiple Airlines
Deal found 11/11$973
This WestJet deal was found by Cheapflights users on 11/11. 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 12/269:50 amMDW - YLW
2 stops14h 54mWestJet
Fri 1/211:40 pmYLW - MDW
2 stops34h 18mWestJet
Deal found 11/11$1,081
This WestJet deal was found by Cheapflights users on 11/10. 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.
Mon 11/241:47 pmMDW - YLW
2 stops12h 08mWestJet
Thu 11/277:55 pmYLW - MDW
2 stops11h 57mWestJet
Deal found 11/10$1,120

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 November 13, 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

Fri 1/23

11:00 am-10:44 pm

1 stop13h 44m

Kelowna

Sat 1/31

12:35 pm-3:20 pm

2 stops24h 45m

$288

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 1/23

11:00 am-11:55 pm

3 stops14h 55m

Kelowna

Sun 2/1

12:35 pm-10:05 am

2 stops19h 30m

$441

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 4/28

1:00 pm-9:49 pm

2 stops10h 49m

Kelowna

Wed 4/29

11:30 pm-6:31 pm

2 stops17h 01m

$497

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 1/23

1:49 pm-10:24 am

3 stops22h 35m

Kelowna

Sat 1/31

2:15 pm-6:36 pm

3 stops26h 21m

$598

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 3/15

11:00 am-8:02 am

3 stops23h 02m

Kelowna

Fri 3/20

4:00 pm-11:50 am

3 stops17h 50m

$739

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 1/8

1:49 pm-11:55 pm

2 stops12h 06m

Kelowna

Fri 1/16

9:05 am-10:09 pm

2 stops11h 04m

$754

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 1/15

9:13 am-9:34 am

3 stops26h 21m

$151

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 12/9

11:00 am-11:03 am

1 stop26h 03m

$210

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 12/11

11:00 am-11:03 am

1 stop26h 03m

$211

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 12/9

11:00 am-11:55 pm

2 stops14h 55m

$211

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

Showing 1-10 of 14 results
1
2

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 November.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Kelowna flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.

  • 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.

See more FAQs

Traveling to a place near Kelowna?

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

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