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Cheap flights from Chicago Midway Airport to Kelowna from C$ 309

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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YLW
28 May — 4 Jun1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Midway to Kelowna

Enter your travel dates to find the best prices.

Cheapest flights from Midway to Kelowna
Explore the most affordable flight options available from Midway to Kelowna. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 28 April 2026.

Tue 9/610:25 a.m.
MDW
-
YLW
3 stops22h 35m
Multiple Airlines
Tue 16/612:50 p.m.
YLW
-
MDW
2 stops18h 50m
Multiple Airlines
Deal found 25/4C$ 999
Sat 23/510:30 a.m.
MDW
-
YLW
2 stops13h 35m
Multiple Airlines
Sat 30/58:15 p.m.
YLW
-
MDW
2 stops16h 20m
Multiple Airlines
Deal found 23/4C$ 1,029
Sun 10/51:22 p.m.
MDW
-
YLW
2 stops10h 43m
Delta
Mon 18/56:05 a.m.
YLW
-
MDW
2 stops10h 28m
Delta
Deal found 23/4C$ 1,074
Wed 10/69:17 a.m.
MDW
-
YLW
3 stops26h 28m
Multiple Airlines
Wed 17/612:50 p.m.
YLW
-
MDW
2 stops18h 50m
Multiple Airlines
Deal found 26/4C$ 1,108
Fri 5/69:22 a.m.
MDW
-
YLW
3 stops28h 33m
Multiple Airlines
Sun 7/612:50 p.m.
YLW
-
MDW
2 stops18h 45m
Multiple Airlines
Deal found 26/4C$ 1,141
Tue 9/610:25 a.m.
MDW
-
YLW
2 stops27h 30m
Porter Airlines
Tue 16/612:50 p.m.
YLW
-
MDW
2 stops18h 50m
Porter Airlines
Deal found 25/4C$ 1,182
Fri 26/61:21 p.m.
MDW
-
YLW
2 stops23h 26m
Multiple Airlines
Sun 5/712:50 p.m.
YLW
-
MDW
2 stops18h 50m
Multiple Airlines
Deal found 26/4C$ 1,204
Tue 9/69:17 a.m.
MDW
-
YLW
3 stops16h 13m
WestJet
Tue 16/63:15 p.m.
YLW
-
MDW
3 stops19h 21m
WestJet
Deal found 25/4C$ 1,225
Wed 10/610:15 a.m.
MDW
-
YLW
2 stops15h 35m
Multiple Airlines
Mon 15/610:20 a.m.
YLW
-
MDW
3 stops21h 15m
Multiple Airlines
Deal found 26/4C$ 1,238

Find flight deals from Midway to Kelowna

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Kelowna (YLW). 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 28 April 2026.

Round-trip from

C$ 999

One-way from

C$ 309
Porter Airlines
  • Porter Airlines
  • 9/6-16/6
  • 5 total stops
  • 41h 25m total
  • Chicago to Kelowna
Search Deals
Delta
  • Delta
  • 11/6
  • 2 total stops
  • 11h 41m total
  • Chicago to Kelowna
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Kelowna 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 28 April 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Kelowna that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 9/6

10:25 a.m.-7:00 a.m.

3 stops22h 35m

Kelowna

Tue 16/6

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

2 stops18h 50m

C$ 999

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sat 23/5

10:30 a.m.-10:05 p.m.

2 stops13h 35m

Kelowna

Sat 30/5

8:15 p.m.-2:35 p.m.

2 stops16h 20m

C$ 1,029
Quickest round-trip

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 10/5

1:22 p.m.-10:05 p.m.

2 stops10h 43m

Kelowna

Mon 18/5

6:05 a.m.-6:33 p.m.

2 stops10h 28m

C$ 1,074

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Wed 10/6

9:17 a.m.-9:45 a.m.

3 stops26h 28m

Kelowna

Wed 17/6

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

2 stops18h 50m

C$ 1,108

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 9/6

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

2 stops27h 30m

Kelowna

Tue 16/6

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

2 stops18h 50m

C$ 1,182

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 26/6

9:17 a.m.-11:55 a.m.

3 stops28h 38m

Kelowna

Sun 5/7

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

2 stops18h 50m

C$ 1,204

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 9/6

9:17 a.m.-11:30 p.m.

3 stops16h 13m

Kelowna

Tue 16/6

3:15 p.m.-12:36 p.m.

3 stops19h 21m

C$ 1,225

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Wed 10/6

10:15 a.m.-11:50 p.m.

2 stops15h 35m

Kelowna

Mon 15/6

10:20 a.m.-9:35 a.m.

3 stops21h 15m

C$ 1,238

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 5/6

6:36 p.m.-11:55 a.m.

3 stops19h 19m

Kelowna

Sun 7/6

7:50 p.m.-6:31 p.m.

3 stops20h 41m

C$ 1,242

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 11/8

1:00 p.m.-11:50 p.m.

2 stops12h 50m

Kelowna

Sun 16/8

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

2 stops10h 26m

C$ 1,423

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/4

Showing 1-10 of 14 resultsSorted by cheapest first
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Best time to book a flight from Midway to Kelowna

Have a flexible travel schedule? Discover the best time to fly to Kelowna from Midway 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 Midway to Kelowna. 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 into for flights to Kelowna from Chicago Midway?

    For a flight from Chicago Midway to Kelowna, you will be flying into Kelowna. Kelowna (YLW) is just 11.2 km from the centre of the city. Kelowna is the only Kelowna airport and it handles 0 inbound flights from Chicago Midway per day. 0 airlines have flights to Kelowna from Chicago Midway on a regular basis.

  • How long is the flight from Chicago Midway Airport to Kelowna?

    Departing from Chicago Midway Airport to Kelowna will take you 10h 43m. There are 2586 km between Chicago Midway Airport and Kelowna. Both multi-stop and direct flights can be found to your destination and back.

  • Can I find deals for flights from Midway to Kelowna that include hotel bookings?

    Yes. In addition to deals on Midway to Kelowna flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Kelowna?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Kelowna.

  • Can I find deals for business class flights from Midway to Kelowna?

    Yes. Cheapflights offers flight deals from Midway to Kelowna 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

Travelling to a place near Kelowna?

Book flights to Kelowna if you plan to visit one of these locations
Salmon Arm
West Kelowna
Big White

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