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Cheap flights from Kelowna to Chicago Midway Airport from C$ 358

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 31/8. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — MDW
19 Aug — 26 Aug1
1 adult

Cheap flight deals from Kelowna to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Kelowna (YLW) to Midway (MDW). 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 14 August 2025.

Round-trip from

C$ 1,118

One-way from

C$ 358

Popular in

March

Cheapest in

December

Average price

C$ 483
Delta
  • Delta
  • 4/11-9/11
  • 4 total stops
  • 25h 15m total
  • Kelowna to Chicago
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31/8
  • 31/8
  • 2 total stops
  • 16h 50m total
  • Kelowna to Chicago
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Highest demand for flights based on searches. 15% potential increase in price (C$ 141 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease (C$ 36 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Kelowna to Midway

Cheapest flights from Kelowna to Midway
Explore the most affordable flight options available from Kelowna to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 14 August 2025.

Tue 4/117:55 p.m.YLW - MDW
2 stops11h 50mDelta
Sun 9/1110:35 a.m.MDW - YLW
2 stops13h 25mDelta
Deal found 13/8C$ 1,118

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kelowna to Midway 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 14 August 2025.
Use the filters below to find and compare flights from Kelowna to Chicago Midway Airport that are best for you.

Fly from

Kelowna

Fly to

Midway

Route

Depart

Return

Price

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 4/11

7:55 p.m.-9:45 a.m.

2 stops11h 50m

Chicago Midway

Sun 9/11

10:35 a.m.-10:00 p.m.

2 stops13h 25m

C$ 1,118

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sun 31/8

5:55 a.m.-12:45 a.m.

2 stops16h 50m

C$ 358

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Mon 1/9

5:55 a.m.-9:02 a.m.

2 stops25h 07m

C$ 534

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Mon 8/9

7:45 p.m.-5:37 p.m.

2 stops19h 52m

C$ 626

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 9/10

8:45 p.m.-5:43 p.m.

2 stops18h 58m

C$ 1,121

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/8

Best time to book a flight from Kelowna to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Kelowna 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 Kelowna to Midway. 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 from for flights from Kelowna to Chicago Midway?

    Located just 11.2 km from the city centre, Kelowna is the airport most travellers will use when flying to Chicago Midway from Kelowna. Booking flights from Kelowna (YLW) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 0 different airlines.

  • Can I find deals for flights from Kelowna to Midway that include hotel bookings?

    Yes. In addition to deals on Kelowna to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kelowna to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kelowna to Midway.

  • Can I find deals for business class flights from Kelowna to Midway?

    Yes. Cheapflights offers flight deals from Kelowna to Midway 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 Kelowna to Chicago Midway Airport?

    Currently, June is the cheapest month in which you can book a flight from Kelowna to Chicago Midway Airport (average of C$ 233). Flying from Kelowna to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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.

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Why should you use Cheapflights to find cheap flight tickets from Kelowna to Midway?

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Can Cheapflights find flights from Kelowna to Midway with no change fees?

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