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Cheap flights from Kelowna to Chicago Midway Airport from C$ 357

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 15/7. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — MDW
22 Jun — 29 Jun1
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
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 23 May 2026.

Tue 1/1211:40 p.m.
YLW
-
MDW
2 stops10h 53m
Delta
Sat 5/1212:30 p.m.
MDW
-
YLW
2 stops14h 23m
Delta
Deal found 21/5C$ 545
Mon 5/106:05 a.m.
YLW
-
MDW
2 stops10h 26m
Delta
Thu 8/1012:30 p.m.
MDW
-
YLW
2 stops13h 00m
Delta
Deal found 20/5C$ 642
Wed 1/712:50 p.m.
YLW
-
MDW
2 stops18h 50m
Multiple Airlines
Wed 8/710:20 a.m.
MDW
-
YLW
3 stops22h 40m
Multiple Airlines
Deal found 21/5C$ 992
Wed 8/712:50 p.m.
YLW
-
MDW
2 stops18h 50m
Multiple Airlines
Wed 15/79:19 a.m.
MDW
-
YLW
3 stops28h 36m
Multiple Airlines
Deal found 21/5C$ 998
Thu 2/712:50 p.m.
YLW
-
MDW
2 stops18h 50m
Porter Airlines
Wed 8/73:15 p.m.
MDW
-
YLW
2 stops22h 40m
Porter Airlines
Deal found 19/5C$ 1,036
Wed 3/612:50 p.m.
YLW
-
MDW
2 stops18h 45m
Multiple Airlines
Fri 5/610:15 a.m.
MDW
-
YLW
3 stops22h 45m
Multiple Airlines
Deal found 20/5C$ 1,046
Wed 1/712:50 p.m.
YLW
-
MDW
2 stops23h 45m
Porter Airlines
Wed 8/73:15 p.m.
MDW
-
YLW
2 stops22h 40m
Porter Airlines
Deal found 21/5C$ 1,070
Wed 15/712:50 p.m.
YLW
-
MDW
2 stops18h 50m
Porter Airlines
Wed 22/73:15 p.m.
MDW
-
YLW
2 stops22h 40m
Porter Airlines
Deal found 20/5C$ 1,071
Thu 2/712:50 p.m.
YLW
-
MDW
2 stops18h 50m
Porter Airlines
Fri 3/73:15 p.m.
MDW
-
YLW
2 stops22h 40m
Porter Airlines
Deal found 19/5C$ 1,097

Find 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 23 May 2026.

Round-trip from

C$ 642

One-way from

C$ 357

Popular in

September

Cheapest in

May

Average price

C$ 400
Delta
  • Delta
  • 5/10-8/10
  • 4 total stops
  • 23h 26m total
  • Kelowna to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 15/7
  • 2 total stops
  • 18h 50m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (C$ 62 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

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 23 May 2026.
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 - MDW

YLWMDW

Kelowna

Tue 20/10

6:05 a.m.-6:37 p.m.

2 stops10h 32m

Chicago Midway

Sat 24/10

1:00 p.m.-10:05 p.m.

2 stops11h 05m

C$ 642

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Mon 5/10

6:05 a.m.-6:31 p.m.

2 stops10h 26m

Chicago Midway

Thu 8/10

12:30 p.m.-11:30 p.m.

2 stops13h 00m

C$ 642

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 8/7

12:50 p.m.-9:40 a.m.

2 stops18h 50m

Chicago Midway

Wed 15/7

9:19 a.m.-11:55 a.m.

3 stops28h 36m

C$ 998

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 3/6

12:50 p.m.-9:35 a.m.

2 stops18h 45m

Chicago Midway

Fri 5/6

10:15 a.m.-7:00 a.m.

3 stops22h 45m

C$ 1,046

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 1/7

12:50 p.m.-2:35 p.m.

2 stops23h 45m

Chicago Midway

Wed 8/7

3:15 p.m.-11:55 a.m.

2 stops22h 40m

C$ 1,070

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 30/6

12:50 p.m.-2:35 p.m.

2 stops23h 45m

Chicago Midway

Wed 8/7

3:15 p.m.-11:55 a.m.

2 stops22h 40m

C$ 1,145

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 30/6

12:50 p.m.-9:40 a.m.

2 stops18h 50m

Chicago Midway

Tue 7/7

3:15 p.m.-11:55 a.m.

2 stops22h 40m

C$ 1,148

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 30/6

12:50 p.m.-9:40 a.m.

2 stops18h 50m

Chicago Midway

Wed 1/7

3:15 p.m.-11:55 a.m.

2 stops22h 40m

C$ 1,158

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sun 28/6

12:50 p.m.-9:40 a.m.

2 stops18h 50m

Chicago Midway

Tue 7/7

3:15 p.m.-11:55 a.m.

2 stops22h 40m

C$ 1,163
Cheapest one-way

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 28/7

3:10 p.m.-10:08 p.m.

3 stops28h 58m

C$ 371

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/5

Showing 1-10 of 16 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
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 32m. 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.

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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