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Cheap flights from Kelowna to Chicago Midway Airport from C$ 268

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 14/4. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — MDW
2 Apr — 9 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap 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 3 March 2026.

Fri 5/66:05 a.m.
YLW
-
MDW
2 stops9h 51m
WestJet
Tue 16/61:00 p.m.
MDW
-
YLW
2 stops11h 05m
WestJet
Deal found 3/3C$ 1,041
Wed 11/32:15 p.m.
YLW
-
MDW
2 stops17h 50m
Multiple Airlines
Wed 18/311:00 a.m.
MDW
-
YLW
1 stop26h 03m
Multiple Airlines
Deal found 3/3C$ 1,081
Sat 7/312:35 p.m.
YLW
-
MDW
3 stops26h 19m
WestJet
Sat 14/39:35 a.m.
MDW
-
YLW
3 stops24h 30m
WestJet
Deal found 27/2C$ 1,174
Mon 2/36:35 p.m.
YLW
-
MDW
2 stops40h 30m
WestJet
Wed 4/37:20 p.m.
MDW
-
YLW
2 stops30h 33m
WestJet
Deal found 26/2C$ 1,457

Find 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 3 March 2026.

Round-trip from

C$ 1,018

One-way from

C$ 268

Popular in

July

Cheapest in

June

Average price

C$ 469
WestJet
  • WestJet
  • 15/4-22/4
  • 4 total stops
  • 24h 18m total
  • Kelowna to Chicago
Search Deals
14/4
  • 14/4
  • 2 total stops
  • 14h 54m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 71 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 46 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 3 March 2026.
Use the filters below to find and compare flights from Kelowna to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 5/6

6:05 a.m.-5:56 p.m.

2 stops9h 51m

Chicago Midway

Tue 16/6

1:00 p.m.-10:05 p.m.

2 stops11h 05m

C$ 1,041

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 14/4

5:20 a.m.-10:14 p.m.

2 stops14h 54m

C$ 268

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 16/4

7:35 p.m.-10:14 p.m.

3 stops48h 39m

C$ 310

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 10/4

11:40 p.m.-5:54 p.m.

2 stops16h 14m

C$ 317

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 10/4

7:55 p.m.-3:20 p.m.

3 stops41h 25m

C$ 364

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 10/3

3:00 p.m.-10:05 a.m.

2 stops17h 05m

C$ 489

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 10/3

12:00 p.m.-10:05 a.m.

1 stop20h 05m

C$ 540

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/2

Sorted by cheapest first

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 9h 51m. 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.

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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?

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?

Of course! You can now track prices for flights from Kelowna to Midway and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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