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Cheap flights from Kelowna to Chicago Midway Airport from C$ 338

YLW — MDW
13 Oct — 20 Oct1
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

Thu 22/106:05 a.m. -
2 stops9h 55m
Tue 27/1012:27 p.m. -
2 stops12h 58m
Deal found 12/9C$ 485
Sat 17/106:05 a.m. -
2 stops9h 55m
Wed 21/101:27 p.m. -
2 stops10h 38m
Deal found 8/9C$ 731
Thu 24/910:50 p.m. -
1 stop13h 45m
Mon 28/911:45 a.m. -
1 stop12h 07m
Deal found 10/9C$ 784
Thu 24/910:50 p.m. -
1 stop13h 45m
Mon 28/96:25 a.m. -
2 stops15h 00m
Deal found 10/9C$ 792
Tue 27/108:25 p.m. -
2 stops13h 29m
Tue 3/1112:27 p.m. -
2 stops13h 48m
Deal found 12/9C$ 907
Tue 22/128:25 p.m. -
2 stops10h 48m
Sat 2/16:20 p.m. -
2 stops27h 05m
Deal found 8/9C$ 1,315

Find flight deals from Kelowna to Midway

Round-trip from

C$ 485

One-way from

C$ 338

Popular in

December

Cheapest in

May

Average price

C$ 972
Delta
  • Delta
  • 21/10-28/10
  • 4 total stops
  • 22h 53m total
  • Kelowna to Chicago
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7/10-31/12
  • 7/10-31/12
  • 2 total stops
  • 19h 30m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 40% potential increase in price (C$ 728 potential increase over avg. RT price).
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Cheapest flight prices on average. 15% potential price decrease (C$ 146 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2026
Search Deals

Cheapflights Fare Finder

 
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

Cheapest round-trip
Quickest round-trip

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Wed 7/10

8:15 p.m.-5:45 p.m.

2 stops19h 30m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 338

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sun 25/10

8:25 p.m.-11:43 p.m.

2 stops25h 18m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 348

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Wed 21/10

8:15 p.m.-11:43 p.m.

2 stops25h 28m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 381

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Wed 21/10

6:05 a.m.-6:00 p.m.

2 stops9h 55m

Chicago Midway

Wed 28/10

12:27 p.m.-11:25 p.m.

2 stops12h 58m

C$ 485

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Thu 22/10

6:05 a.m.-6:00 p.m.

2 stops9h 55m

Chicago Midway

Tue 27/10

12:27 p.m.-11:25 p.m.

2 stops12h 58m

C$ 485

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sat 17/10

6:05 a.m.-6:00 p.m.

2 stops9h 55m

Chicago Midway

Wed 21/10

1:27 p.m.-10:05 p.m.

2 stops10h 38m

C$ 731

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Thu 24/9

10:50 p.m.-2:35 p.m.

1 stop13h 45m

Chicago Midway

Mon 28/9

6:25 a.m.-7:25 p.m.

2 stops15h 00m

C$ 792

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Tue 27/10

8:25 p.m.-11:54 a.m.

2 stops13h 29m

Chicago Midway

Tue 3/11

12:27 p.m.-1:15 a.m.

2 stops13h 48m

C$ 907

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Wed 21/10

6:05 a.m.-6:00 p.m.

2 stops9h 55m

Chicago Midway

Wed 28/10

12:27 p.m.-11:25 p.m.

2 stops12h 58m

C$ 1,326

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Thu 24/9

6:30 p.m.-9:49 a.m.

2 stops13h 19m

Chicago Midway

Mon 28/9

1:19 p.m.-10:05 p.m.

2 stops10h 46m

C$ 1,334

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

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

Related info for your journey

  • 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 55m. 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.

See more FAQs

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