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Cheap flights from Chicago Midway Airport to Kelowna from C$ 1,187

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 25/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YLW
27 Nov — 4 Dec1
1 adult
1 adult, Economy, 0 bags

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 28 October 2025.

Round-trip from

C$ 1,187

Popular in

October

Cheapest in

March

Average price

C$ 1,580
25/12-1/1
  • 25/12-1/1
  • 5 total stops
  • 41h 56m total
  • Chicago to Kelowna
Search Deals
Highest demand for flights based on searches. 29% potential increase in price (C$ 423 potential increase over avg. RT price).
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Cheapest flight prices on average. 12% potential price decrease (C$ 119 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Midway to Kelowna

Enter your travel dates to find the best prices.

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 28 October 2025.

Thu 25/124:15 p.m.MDW - YLW
3 stops23h 36mMultiple Airlines
Thu 1/17:00 p.m.YLW - MDW
2 stops18h 20mMultiple Airlines
Deal found 27/10C$ 1,187
Tue 11/117:02 p.m.MDW - YLW
2 stops21h 32mWestJet
Tue 18/118:55 a.m.YLW - MDW
2 stops31h 23mWestJet
Deal found 27/10C$ 1,330

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 629,999 searches. Data last updated 28 October 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 25/12

4:15 p.m.-1:51 p.m.

3 stops23h 36m

Kelowna

Thu 1/1

7:00 p.m.-3:20 p.m.

2 stops18h 20m

C$ 1,187

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 11/11

7:02 p.m.-2:34 p.m.

2 stops21h 32m

Kelowna

Tue 18/11

8:55 a.m.-6:18 p.m.

2 stops31h 23m

C$ 1,330

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 7/4

9:20 a.m.-11:53 p.m.

2 stops16h 33m

Kelowna

Wed 8/4

10:10 a.m.-9:56 a.m.

2 stops21h 46m

C$ 1,428

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/10

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?

    For a flight from Chicago Midway to Kelowna, you will be flying into Kelowna. Kelowna (YLW) is just 11.2 km from the centre of the city. Kelowna is the only Kelowna airport and it handles 0 inbound flights from Chicago Midway per day. 0 airlines have flights to Kelowna from Chicago Midway on a regular basis.

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

    Departing from Chicago Midway Airport to Kelowna will take you 21h 32m. There are 2586 km between Chicago Midway Airport and Kelowna.

  • 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

Travelling to a place near Kelowna?

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

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