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Cheap flights from Kelowna to Chicago Midway Airport from C$ 238

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 26/10. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — MDW
11 Oct — 18 Oct1
1 adult
1 adult, Economy

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 11 September 2025.

Round-trip from

C$ 1,408

One-way from

C$ 238

Popular in

March

Cheapest in

April

Average price

C$ 608
Delta
  • Delta
  • 20/12-6/1
  • 4 total stops
  • 25h 57m total
  • Kelowna to Chicago
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26/10
  • 26/10
  • 3 total stops
  • 38h 03m total
  • Kelowna to Chicago
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Highest demand for flights based on searches. 13% potential increase in price (C$ 127 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease (C$ 35 potential savings vs. average RT price).
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Average for round-trip flights in September 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 11 September 2025.

Thu 18/910:10 a.m.YLW - MDW
2 stops20h 29mMultiple Airlines
Thu 2/109:35 a.m.MDW - YLW
1 stop27h 25mMultiple Airlines
Deal found 10/9C$ 876
Thu 18/911:55 a.m.YLW - MDW
1 stop18h 44mPorter Airlines
Thu 2/105:20 p.m.MDW - YLW
1 stop19h 40mPorter Airlines
Deal found 10/9C$ 1,049
Sat 20/127:55 p.m.YLW - MDW
2 stops14h 02mDelta
Tue 6/12:00 p.m.MDW - YLW
2 stops11h 55mDelta
Deal found 11/9C$ 1,408

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 11 September 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

Sat 20/12

7:55 p.m.-11:57 a.m.

2 stops14h 02m

Chicago Midway

Tue 6/1

2:00 p.m.-11:55 p.m.

2 stops11h 55m

C$ 1,408

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sun 26/10

7:35 p.m.-11:38 a.m.

3 stops38h 03m

C$ 238

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sun 21/12

11:40 p.m.-5:20 p.m.

2 stops15h 40m

C$ 637

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Mon 22/12

11:40 p.m.-5:20 p.m.

2 stops15h 40m

C$ 711

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sat 20/12

7:55 p.m.-11:57 a.m.

2 stops14h 02m

C$ 989

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 23/12

7:55 p.m.-9:09 a.m.

2 stops11h 14m

C$ 1,116

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

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.

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

    Departing from Kelowna to Chicago Midway Airport will take you 14h 02m. Airlines will cover a distance of 2586 km.

  • 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, September is the cheapest month in which you can book a flight from Kelowna to Chicago Midway Airport (average of C$ 209). 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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