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Cheap flights from Chicago Midway Airport to Kelowna from C$ 261

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 19/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YLW
9 Apr — 16 Apr1
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 10 March 2026.

Wed 27/510:25 a.m.
MDW
-
YLW
1 stop26h 22m
Multiple Airlines
Mon 1/67:50 p.m.
YLW
-
MDW
2 stops16h 45m
Multiple Airlines
Deal found 6/3C$ 725
Mon 6/44:05 p.m.
MDW
-
YLW
2 stops19h 26m
Multiple Airlines
Mon 13/412:55 p.m.
YLW
-
MDW
2 stops19h 20m
Multiple Airlines
Deal found 9/3C$ 784
Wed 27/51:22 p.m.
MDW
-
YLW
2 stops10h 43m
Delta
Mon 1/66:05 a.m.
YLW
-
MDW
2 stops10h 28m
Delta
Deal found 6/3C$ 959
Wed 27/53:20 p.m.
MDW
-
YLW
1 stop21h 27m
Porter Airlines
Mon 1/611:45 a.m.
YLW
-
MDW
1 stop24h 50m
Porter Airlines
Deal found 6/3C$ 996
Thu 11/61:00 p.m.
MDW
-
YLW
2 stops12h 50m
Delta
Tue 16/66:05 a.m.
YLW
-
MDW
2 stops10h 26m
Delta
Deal found 6/3C$ 1,039
Fri 24/42:12 p.m.
MDW
-
YLW
2 stops11h 41m
Delta
Wed 29/46:35 p.m.
YLW
-
MDW
2 stops15h 32m
Delta
Deal found 8/3C$ 1,232
Thu 11/610:25 a.m.
MDW
-
YLW
3 stops15h 25m
Multiple Airlines
Tue 16/66:30 p.m.
YLW
-
MDW
3 stops18h 05m
Multiple Airlines
Deal found 6/3C$ 1,297
Fri 18/121:00 p.m.
MDW
-
YLW
2 stops11h 44m
WestJet
Fri 25/127:35 p.m.
YLW
-
MDW
2 stops12h 17m
WestJet
Deal found 5/3C$ 1,362
Sat 26/125:59 p.m.
MDW
-
YLW
2 stops30h 45m
WestJet
Sat 2/110:10 a.m.
YLW
-
MDW
2 stops21h 42m
WestJet
Deal found 6/3C$ 1,391
Tue 21/49:29 a.m.
MDW
-
YLW
2 stops16h 24m
WestJet
Tue 28/45:05 a.m.
YLW
-
MDW
2 stops10h 53m
WestJet
Deal found 6/3C$ 1,425

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 10 March 2026.

Round-trip from

C$ 725

One-way from

C$ 261

Popular in

October

Cheapest in

March

Average price

C$ 228
27/5-1/6
  • 27/5-1/6
  • 3 total stops
  • 43h 07m total
  • Chicago to Kelowna
Search Deals
Delta
  • Delta
  • 19/4
  • 2 total stops
  • 15h 14m total
  • Chicago to Kelowna
Search Deals
Highest demand for flights based on searches. 28% potential increase in price (C$ 395 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 14% potential price decrease (C$ 124 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 10 March 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

Wed 27/5

10:25 a.m.-10:47 a.m.

1 stop26h 22m

Kelowna

Mon 1/6

7:50 p.m.-2:35 p.m.

2 stops16h 45m

C$ 725

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 6/4

4:05 p.m.-9:31 a.m.

2 stops19h 26m

Kelowna

Mon 13/4

4:00 p.m.-10:15 a.m.

3 stops16h 15m

C$ 784
Quickest round-trip

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Wed 27/5

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

2 stops10h 43m

Kelowna

Mon 1/6

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

2 stops10h 28m

C$ 959

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 11/6

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

2 stops12h 50m

Kelowna

Tue 16/6

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

2 stops10h 26m

C$ 1,039

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 24/4

2:12 p.m.-11:53 p.m.

2 stops11h 41m

Kelowna

Wed 29/4

6:35 p.m.-12:07 p.m.

2 stops15h 32m

C$ 1,232

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 11/6

10:25 a.m.-11:50 p.m.

3 stops15h 25m

Kelowna

Tue 16/6

6:30 p.m.-2:35 p.m.

3 stops18h 05m

C$ 1,297

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 21/4

9:29 a.m.-11:53 p.m.

2 stops16h 24m

Kelowna

Tue 28/4

5:05 a.m.-5:58 p.m.

2 stops10h 53m

C$ 1,425

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 27/4

9:27 a.m.-10:05 p.m.

2 stops14h 38m

Kelowna

Fri 1/5

4:30 p.m.-6:36 p.m.

2 stops24h 06m

C$ 1,472
Cheapest one-way

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 19/4

9:27 a.m.-10:41 p.m.

2 stops15h 14m

C$ 261

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 19/4

6:38 p.m.-11:22 a.m.

3 stops18h 44m

C$ 404

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/3

Showing 1-10 of 11 resultsSorted by cheapest first
1
2

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.

  • 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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