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Cheap flights from Kelowna to Chicago Midway Airport from C$ 227

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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — MDW
13 Dec — 20 Dec1
1 adult
1 adult, Economy, 0 bags

Find flight deals from Kelowna to Midway

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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 November 2025.

Tue 9/1211:40 p.m.YLW - MDW
2 stops35h 21mMultiple Airlines
Tue 16/1211:00 a.m.MDW - YLW
1 stop26h 03mMultiple Airlines
Deal found 11/11C$ 749
Tue 9/1211:40 p.m.YLW - MDW
2 stops32h 14mWestJet
Tue 16/127:02 p.m.MDW - YLW
2 stops53h 42mWestJet
Deal found 11/11C$ 751
Tue 9/1212:00 p.m.YLW - MDW
1 stop20h 05mPorter Airlines
Tue 16/1211:00 a.m.MDW - YLW
1 stop26h 03mPorter Airlines
Deal found 11/11C$ 804
Wed 3/127:35 p.m.YLW - MDW
2 stops14h 20mDelta
Wed 10/121:50 p.m.MDW - YLW
2 stops12h 05mDelta
Deal found 13/11C$ 1,456
Wed 3/127:35 p.m.YLW - MDW
2 stops14h 20mDelta
Mon 8/121:50 p.m.MDW - YLW
2 stops12h 05mDelta
Deal found 13/11C$ 1,503
Sat 20/127:55 p.m.YLW - MDW
2 stops14h 03mDelta
Tue 6/11:49 p.m.MDW - YLW
2 stops12h 06mDelta
Deal found 11/11C$ 1,579

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 November 2025.

Round-trip from

C$ 749

One-way from

C$ 227

Popular in

November

Cheapest in

April

Average price

C$ 1,006
Porter Airlines
  • Porter Airlines
  • 9/12-16/12
  • 3 total stops
  • 61h 24m total
  • Kelowna to Chicago
Search Deals
7/1
  • 7/1
  • 2 total stops
  • 25h 42m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 80 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 55 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 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 9/12

11:40 p.m.-1:01 p.m.

2 stops35h 21m

Chicago Midway

Tue 16/12

11:00 a.m.-11:03 a.m.

1 stop26h 03m

C$ 749

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 9/12

11:40 p.m.-9:54 a.m.

2 stops32h 14m

Chicago Midway

Tue 16/12

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

2 stops53h 42m

C$ 751

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 9/12

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

1 stop20h 05m

Chicago Midway

Tue 16/12

11:00 a.m.-11:03 a.m.

1 stop26h 03m

C$ 804

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Mon 4/5

5:55 a.m.-6:31 p.m.

2 stops10h 36m

Chicago Midway

Tue 5/5

6:45 p.m.-11:49 p.m.

2 stops31h 04m

C$ 953

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Mon 4/5

5:55 a.m.-9:45 p.m.

2 stops13h 50m

Chicago Midway

Tue 5/5

2:00 p.m.-11:49 p.m.

2 stops11h 49m

C$ 1,074

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Mon 16/2

7:55 p.m.-1:09 p.m.

2 stops15h 14m

Chicago Midway

Sat 21/2

9:50 a.m.-11:53 p.m.

2 stops16h 03m

C$ 1,255

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 3/12

7:35 p.m.-11:55 a.m.

2 stops14h 20m

Chicago Midway

Wed 10/12

1:50 p.m.-11:55 p.m.

2 stops12h 05m

C$ 1,456

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 3/12

7:35 p.m.-11:55 a.m.

2 stops14h 20m

Chicago Midway

Mon 8/12

1:50 p.m.-11:55 p.m.

2 stops12h 05m

C$ 1,503

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sat 20/12

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

2 stops14h 03m

Chicago Midway

Tue 6/1

1:49 p.m.-11:55 p.m.

2 stops12h 06m

C$ 1,579

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 7/1

6:35 p.m.-10:17 p.m.

2 stops25h 42m

C$ 227

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/11

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 36m. 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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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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