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Cheap flights from Kelowna to Chicago Midway Airport from C$ 403

YLW — MDW
24 Oct — 31 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 21/9C$ 486
Wed 21/106:05 a.m. -
2 stops9h 55m
Wed 28/1012:27 p.m. -
2 stops12h 58m
Deal found 21/9C$ 528
Sat 17/106:05 a.m. -
2 stops9h 55m
Wed 21/101:27 p.m. -
2 stops12h 23m
Deal found 22/9C$ 927
Wed 11/118:25 p.m. -
2 stops11h 59m
Mon 16/1112:30 p.m. -
2 stops31h 25m
Deal found 20/9C$ 1,347
Tue 29/912:50 p.m. -
2 stops20h 10m
Fri 2/103:20 p.m. -
3 stops22h 00m
Deal found 19/9C$ 1,465
Mon 28/96:30 p.m. -
2 stops13h 19m
Thu 1/1010:48 a.m. -
2 stops10h 37m
Deal found 19/9C$ 1,477
Tue 3/115:20 a.m. -
2 stops27h 23m
Tue 10/115:29 p.m. -
2 stops26h 26m
Deal found 19/9C$ 1,478

Find flight deals from Kelowna to Midway

Round-trip from

C$ 486

One-way from

C$ 403

Popular in

December

Cheapest in

May

Average price

C$ 988
Delta
  • Delta
  • 22/10-27/10
  • 4 total stops
  • 22h 53m total
  • Kelowna to Chicago
Search Deals
5/11-31/12
  • 5/11-31/12
  • 3 total stops
  • 51h 37m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 30% potential increase in price (C$ 454 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (C$ 86 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 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

Thu 5/11

12:10 p.m.-4:47 p.m.

3 stops51h 37m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 403

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Fri 16/10

5:55 a.m.-11:43 p.m.

2 stops39h 48m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 407

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Tue 3/11

8:00 p.m.-10:25 a.m.

3 stops37h 25m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 431

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$ 528
Quickest round-trip

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Wed 3/2

8:25 p.m.-8:52 a.m.

2 stops11h 27m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 702

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Thu 29/10

8:25 p.m.-10:03 a.m.

2 stops11h 38m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 703

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Fri 20/11

11:35 a.m.-10:50 a.m.

2 stops22h 15m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 745

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$ 927

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sat 17/10

5:55 a.m.-8:44 a.m.

2 stops24h 49m

Chicago Midway

Wed 21/10

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

2 stops10h 38m

C$ 1,068

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Thu 4/2

5:20 a.m.-3:25 p.m.

2 stops9h 05m

Chicago Midway

Mon 8/2

9:55 a.m.-8:25 p.m.

2 stops11h 30m

C$ 1,346

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/9

Showing 1-10 of 14 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 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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Why should you use Cheapflights to find cheap flight tickets from Kelowna to Midway?

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