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Cheap flights from Kelowna to Chicago Midway Airport from C$ 349

YLW — MDW
8 Dec — 15 Dec1
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

Sun 6/1211:35 a.m. -
2 stops28h 15m
Wed 9/1212:39 p.m. -
2 stops28h 51m
Deal found 5/11C$ 831
Sun 6/1211:35 a.m. -
2 stops28h 15m
Wed 9/1210:24 a.m. -
2 stops31h 06m
Deal found 7/11C$ 852
Thu 26/115:20 a.m. -
2 stops28h 05m
Sun 29/115:29 p.m. -
2 stops25h 26m
Deal found 7/11C$ 900
Wed 30/1211:35 a.m. -
2 stops28h 49m
Fri 8/112:44 p.m. -
2 stops12h 36m
Deal found 5/11C$ 1,099
Sat 19/1211:35 a.m. -
2 stops28h 49m
Thu 31/1211:47 a.m. -
2 stops31h 08m
Deal found 8/11C$ 1,222
Thu 26/118:25 p.m. -
2 stops12h 59m
Sun 29/1112:30 p.m. -
2 stops12h 45m
Deal found 4/11C$ 1,503
Wed 23/128:00 p.m. -
2 stops12h 13m
Wed 30/129:58 a.m. -
2 stops13h 22m
Deal found 8/11C$ 1,899

Find flight deals from Kelowna to Midway

Round-trip from

C$ 831

One-way from

C$ 349

Popular in

October

Cheapest in

May

Average price

C$ 788
Delta
  • Delta
  • 6/12-9/12
  • 4 total stops
  • 57h 06m total
  • Kelowna to Chicago
Search Deals
30/1-31/12
  • 30/1-31/12
  • 2 total stops
  • 17h 26m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 205 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 53 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sat 30/1

8:25 p.m.-7:42 p.m.

3 stops22h 17m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 415

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sat 30/1

5:20 a.m.-10:04 a.m.

2 stops27h 44m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 461

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Mon 1/3

8:25 p.m.-4:36 p.m.

2 stops19h 11m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 476

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Fri 20/11

7:55 p.m.-1:45 p.m.

2 stops16h 50m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 483

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Mon 1/3

8:25 p.m.-12:13 p.m.

3 stops38h 48m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 531
Quickest round-trip

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Fri 20/11

5:20 a.m.-4:18 p.m.

2 stops9h 58m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 551

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sun 6/12

11:35 a.m.-4:50 p.m.

2 stops28h 15m

Chicago Midway

Wed 9/12

12:39 p.m.-4:30 p.m.

2 stops28h 51m

C$ 831

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sun 6/12

11:35 a.m.-4:50 p.m.

2 stops28h 15m

Chicago Midway

Wed 9/12

10:24 a.m.-4:30 p.m.

2 stops31h 06m

C$ 852

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Wed 10/3

5:20 a.m.-4:25 p.m.

2 stops10h 05m

Chicago Midway

Tue 23/3

10:35 a.m.-12:55 p.m.

2 stops28h 20m

C$ 874

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Thu 26/11

5:20 a.m.-10:25 a.m.

2 stops28h 05m

Chicago Midway

Sun 29/11

5:29 p.m.-5:55 p.m.

2 stops25h 26m

C$ 900

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

Showing 1-10 of 14 resultsSorted by cheapest first
1
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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 28h 15m. 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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Why should you use Cheapflights to find cheap flight tickets from Kelowna to Midway?

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