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Cheap flights from Chicago Midway Airport to Kelowna from C$ 188

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 24/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YLW
11 Oct — 18 Oct1
1 adult
1 adult, Economy

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 11 September 2025.

Round-trip from

C$ 1,140

One-way from

C$ 188

Popular in

December

Cheapest in

March

Average price

C$ 502
28/12-2/1
  • 28/12-2/1
  • 3 total stops
  • 28h 34m total
  • Chicago to Kelowna
Search Deals
Delta
  • Delta
  • 24/10
  • 2 total stops
  • 14h 14m total
  • Chicago to Kelowna
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 144 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 42 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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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 11 September 2025.

Sun 28/1211:00 a.m.MDW - YLW
1 stop13h 44mMultiple Airlines
Fri 2/17:00 p.m.YLW - MDW
2 stops14h 50mMultiple Airlines
Deal found 10/9C$ 1,140
Sun 28/1211:48 a.m.MDW - YLW
2 stops14h 07mWestJet
Fri 2/16:35 p.m.YLW - MDW
2 stops12h 34mWestJet
Deal found 10/9C$ 1,574

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 11 September 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

Sun 28/12

11:00 a.m.-10:44 p.m.

1 stop13h 44m

Kelowna

Fri 2/1

7:00 p.m.-11:50 a.m.

2 stops14h 50m

C$ 1,140

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 28/12

11:48 a.m.-11:55 p.m.

2 stops14h 07m

Kelowna

Fri 2/1

6:35 p.m.-9:09 a.m.

2 stops12h 34m

C$ 1,574

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 24/10

9:35 a.m.-9:49 p.m.

2 stops14h 14m

C$ 188

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 26/10

7:50 a.m.-6:59 p.m.

2 stops13h 09m

C$ 205

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 24/10

12:03 p.m.-11:34 p.m.

3 stops13h 31m

C$ 333

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 22/2

2:00 p.m.-11:53 p.m.

2 stops11h 53m

C$ 887

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 18/9

9:20 a.m.-5:47 p.m.

2 stops10h 27m

C$ 1,201

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

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 14h 07m. 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.

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

    Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Kelowna (average of C$ 137). Flying from Chicago Midway Airport to Kelowna in December is currently the most expensive (average of C$ 239). 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

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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