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Cheap flights from Kelowna to Chicago Midway Airport from C$ 381

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 19/8. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — MDW
5 Jul — 12 Jul1
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 5 June 2026.

Wed 21/106:05 a.m.
YLW
-
MDW
2 stops10h 32m
Delta
Sat 24/1012:30 p.m.
MDW
-
YLW
2 stops13h 20m
Delta
Deal found 4/6C$ 624
Wed 19/88:15 p.m.
YLW
-
MDW
2 stops12h 57m
Multiple Airlines
Mon 24/810:20 a.m.
MDW
-
YLW
1 stop13h 32m
Multiple Airlines
Deal found 5/6C$ 912
Wed 19/811:45 a.m.
YLW
-
MDW
1 stop24h 50m
Porter Airlines
Mon 24/810:20 a.m.
MDW
-
YLW
1 stop13h 32m
Porter Airlines
Deal found 5/6C$ 1,029
Wed 19/88:15 p.m.
YLW
-
MDW
2 stops13h 36m
Delta
Mon 24/81:51 p.m.
MDW
-
YLW
2 stops11h 39m
Delta
Deal found 5/6C$ 1,050
Thu 2/712:50 p.m.
YLW
-
MDW
2 stops18h 50m
Porter Airlines
Tue 7/710:25 a.m.
MDW
-
YLW
2 stops27h 30m
Porter Airlines
Deal found 2/6C$ 1,051
Tue 30/612:50 p.m.
YLW
-
MDW
2 stops23h 45m
Porter Airlines
Wed 8/710:25 a.m.
MDW
-
YLW
2 stops27h 30m
Porter Airlines
Deal found 2/6C$ 1,125
Sat 5/96:00 a.m.
YLW
-
MDW
2 stops7h 57m
WestJet
Fri 11/91:00 p.m.
MDW
-
YLW
2 stops11h 05m
WestJet
Deal found 1/6C$ 1,157
Thu 16/712:50 p.m.
YLW
-
MDW
2 stops23h 45m
Porter Airlines
Thu 23/710:25 a.m.
MDW
-
YLW
2 stops27h 30m
Porter Airlines
Deal found 1/6C$ 1,223
Wed 8/712:50 p.m.
YLW
-
MDW
2 stops23h 45m
Porter Airlines
Tue 14/710:25 a.m.
MDW
-
YLW
2 stops27h 30m
Porter Airlines
Deal found 2/6C$ 1,243

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 5 June 2026.

Round-trip from

C$ 624

One-way from

C$ 381

Popular in

September

Cheapest in

May

Average price

C$ 669
Delta
  • Delta
  • 21/10-24/10
  • 4 total stops
  • 23h 52m total
  • Kelowna to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 19/8
  • 2 total stops
  • 23h 45m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 83 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (C$ 64 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 5 June 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

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 21/10

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

2 stops10h 32m

Chicago Midway

Sat 24/10

12:30 p.m.-11:50 p.m.

2 stops13h 20m

C$ 624

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 19/8

8:15 p.m.-11:51 a.m.

2 stops13h 36m

Chicago Midway

Mon 24/8

1:51 p.m.-11:30 p.m.

2 stops11h 39m

C$ 1,050

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 30/6

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

2 stops23h 45m

Chicago Midway

Wed 8/7

10:25 a.m.-11:55 a.m.

2 stops27h 30m

C$ 1,125

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 19/8

2:30 p.m.-9:17 a.m.

3 stops16h 47m

Chicago Midway

Mon 24/8

6:42 p.m.-11:55 a.m.

3 stops19h 13m

C$ 1,155
Quickest round-trip

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sat 5/9

6:00 a.m.-3:57 p.m.

2 stops7h 57m

Chicago Midway

Fri 11/9

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

2 stops11h 05m

C$ 1,157

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 16/7

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

2 stops23h 45m

Chicago Midway

Thu 23/7

10:25 a.m.-11:55 a.m.

2 stops27h 30m

C$ 1,223

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 8/7

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

2 stops23h 45m

Chicago Midway

Tue 14/7

10:25 a.m.-11:55 a.m.

2 stops27h 30m

C$ 1,243

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 17/11

10:20 a.m.-10:51 a.m.

2 stops23h 31m

Chicago Midway

Wed 18/11

6:45 p.m.-12:44 a.m.

2 stops30h 59m

C$ 1,305

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sat 4/7

6:05 a.m.-5:54 p.m.

2 stops9h 49m

Chicago Midway

Thu 9/7

9:54 a.m.-7:00 p.m.

2 stops11h 06m

C$ 1,379
Cheapest one-way

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 19/8

8:15 p.m.-10:11 p.m.

2 stops23h 56m

C$ 399

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

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
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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