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Cheap flights from Chicago Midway Airport to Kelowna from C$ 234

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 13/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YLW
11 Jan — 18 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap 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 12 December 2025.

Thu 25/126:08 p.m.MDW - YLW
2 stops30h 36mWestJet
Sun 28/128:55 a.m.YLW - MDW
2 stops24h 11mWestJet
Deal found 9/12C$ 1,749
Fri 26/129:50 a.m.MDW - YLW
2 stops14h 54mWestJet
Mon 29/124:00 p.m.YLW - MDW
2 stops23h 19mWestJet
Deal found 9/12C$ 1,918

Find 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 12 December 2025.

Round-trip from

C$ 608

One-way from

C$ 234

Popular in

October

Cheapest in

March

Average price

C$ 1,454
21/1-25/1
  • 21/1-25/1
  • 6 total stops
  • 44h 36m total
  • Chicago to Kelowna
Search Deals
13/1
  • 13/1
  • 2 total stops
  • 12h 11m total
  • Chicago to Kelowna
Search Deals
Highest demand for flights based on searches. 23% potential increase in price (C$ 326 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease (C$ 107 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 12 December 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 21/1

11:00 a.m.-8:06 a.m.

3 stops23h 06m

Kelowna

Sun 25/1

7:00 p.m.-10:10 a.m.

2 stops13h 10m

C$ 608

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 16/1

11:05 a.m.-10:44 p.m.

1 stop13h 39m

Kelowna

Tue 20/1

3:05 p.m.-10:05 a.m.

2 stops17h 00m

C$ 727

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 25/1

1:49 p.m.-11:55 p.m.

2 stops12h 06m

Kelowna

Sun 1/2

7:35 p.m.-11:59 a.m.

2 stops14h 24m

C$ 885

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sat 24/1

11:45 a.m.-11:55 p.m.

2 stops14h 10m

Kelowna

Fri 30/1

9:00 a.m.-10:22 p.m.

2 stops11h 22m

C$ 1,043

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sat 24/1

11:45 a.m.-11:55 p.m.

2 stops14h 10m

Kelowna

Sat 31/1

9:00 a.m.-10:22 p.m.

2 stops11h 22m

C$ 1,084

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 13/2

1:49 p.m.-11:53 p.m.

2 stops12h 04m

Kelowna

Mon 16/2

7:55 p.m.-11:59 a.m.

2 stops14h 04m

C$ 1,178

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 17/2

1:49 p.m.-11:53 p.m.

2 stops12h 04m

Kelowna

Sun 22/2

7:35 p.m.-11:59 a.m.

2 stops14h 24m

C$ 1,218

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 16/1

11:21 a.m.-9:50 p.m.

2 stops12h 29m

Kelowna

Tue 20/1

7:55 p.m.-9:53 a.m.

2 stops11h 58m

C$ 1,310

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Wed 21/1

1:49 p.m.-11:55 p.m.

2 stops12h 06m

Kelowna

Sun 25/1

7:35 p.m.-9:53 a.m.

2 stops12h 18m

C$ 1,310

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 13/1

11:39 a.m.-9:50 p.m.

2 stops12h 11m

C$ 234

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 12 results
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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 12h 06m. 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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