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Cheap flights from Kelowna to Chicago Midway Airport from C$ 347

YLW — MDW
24 Nov — 1 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

Wed 18/118:00 p.m. -
3 stops20h 47m
Wed 25/118:42 p.m. -
3 stops23h 08m
Deal found 21/10C$ 874
Sat 21/1110:45 a.m. -
3 stops32h 02m
Wed 25/118:42 p.m. -
3 stops23h 53m
Deal found 21/10C$ 956
Wed 25/118:25 p.m. -
2 stops12h 59m
Sat 28/1112:30 p.m. -
2 stops12h 45m
Deal found 23/10C$ 1,350
Thu 26/118:25 p.m. -
2 stops12h 59m
Sun 29/1112:30 p.m. -
2 stops12h 45m
Deal found 21/10C$ 1,357
Fri 20/115:20 a.m. -
2 stops9h 58m
Mon 30/1112:30 p.m. -
2 stops33h 20m
Deal found 21/10C$ 1,477
Thu 10/125:20 a.m. -
2 stops10h 30m
Sun 10/19:55 a.m. -
2 stops10h 30m
Deal found 24/10C$ 1,480
Thu 29/108:25 p.m. -
2 stops11h 38m
Thu 5/1112:27 p.m. -
2 stops22h 28m
Deal found 21/10C$ 1,487
Fri 25/127:55 p.m. -
2 stops12h 18m
Fri 1/19:58 a.m. -
2 stops13h 22m
Deal found 25/10C$ 1,546

Find flight deals from Kelowna to Midway

Round-trip from

C$ 874

One-way from

C$ 347

Popular in

October

Cheapest in

May

Average price

C$ 1,045
18/11-25/11
  • 18/11-25/11
  • 6 total stops
  • 43h 55m total
  • Kelowna to Chicago
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5/2-31/12
  • 5/2-31/12
  • 2 total stops
  • 17h 26m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 202 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease (C$ 53 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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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

Fri 22/1

6:05 a.m.-12:13 p.m.

3 stops29h 08m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 378

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sat 21/11

5:20 a.m.-4:39 p.m.

2 stops10h 19m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 398

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Fri 22/1

5:20 a.m.-4:50 p.m.

2 stops10h 30m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 399

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sat 21/11

6:05 a.m.-7:47 p.m.

3 stops36h 42m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 429

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Fri 5/2

3:20 p.m.-12:13 p.m.

3 stops19h 53m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 430

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sat 30/1

5:45 p.m.-12:13 p.m.

3 stops41h 28m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 476
Quickest round-trip

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sat 30/1

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

2 stops10h 05m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 790

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Fri 30/10

7:55 p.m.-10:37 a.m.

2 stops12h 42m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 800

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Wed 18/11

5:20 a.m.-5:47 p.m.

2 stops11h 27m

Chicago Midway

Wed 25/11

8:42 p.m.-6:50 p.m.

3 stops23h 08m

C$ 926

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sat 21/11

10:45 a.m.-7:47 p.m.

3 stops32h 02m

Chicago Midway

Wed 25/11

8:42 p.m.-7:35 p.m.

3 stops23h 53m

C$ 956

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/10

Showing 1-10 of 15 resultsSorted by cheapest first
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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 12h 59m. 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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