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Cheap flights from Kelowna to Chicago Midway Airport from C$ 545

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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — MDW
12 Nov — 19 Nov1
1 adult
1 adult, Economy

Find flight deals from Kelowna to Midway

Enter your travel dates to find the best prices.

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 13 October 2025.

Fri 5/1211:40 p.m.YLW - MDW
2 stops10h 54mDelta
Mon 8/121:50 p.m.MDW - YLW
2 stops26h 44mDelta
Deal found 12/10C$ 545
Fri 5/128:50 a.m.YLW - MDW
3 stops31h 28mWestJet
Mon 8/127:02 p.m.MDW - YLW
2 stops29h 42mWestJet
Deal found 12/10C$ 676
Sat 20/127:55 p.m.YLW - MDW
2 stops14h 03mDelta
Tue 6/12:00 p.m.MDW - YLW
2 stops11h 55mDelta
Deal found 11/10C$ 1,540

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 13 October 2025.

Round-trip from

C$ 545

Popular in

November

Cheapest in

April

Average price

C$ 469
Delta
  • Delta
  • 5/12-8/12
  • 4 total stops
  • 37h 38m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 47 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease (C$ 53 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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 13 October 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

Fri 5/12

11:40 p.m.-12:34 p.m.

2 stops10h 54m

Chicago Midway

Mon 8/12

1:50 p.m.-2:34 p.m.

2 stops26h 44m

C$ 545

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 5/12

8:50 a.m.-6:18 p.m.

3 stops31h 28m

Chicago Midway

Mon 8/12

7:02 p.m.-10:44 p.m.

2 stops29h 42m

C$ 676

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sat 20/12

7:55 p.m.-11:58 a.m.

2 stops14h 03m

Chicago Midway

Tue 6/1

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

2 stops11h 55m

C$ 1,540

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/10

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 10h 54m. Airlines will cover a distance of 2586 km. Both multi-stop and direct flights can be found to your destination and back.

  • 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.

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When you search for this flight from Kelowna to Midway, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

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

Cheapflights simply makes it quick and affordable to book flights from Kelowna to Midway by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

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

Yes, we can. To see specific flights from Kelowna to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Kelowna to Midway become cheaper?

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