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Cheap flights from Chicago Midway Airport to Kelowna from C$ 349

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 31/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YLW
26 Aug — 2 Sep1
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 27 July 2026.

Thu 24/911:45 a.m.
MDW
-
YLW
3 stops14h 05m
Multiple Airlines
Mon 28/98:15 p.m.
YLW
-
MDW
3 stops16h 20m
Multiple Airlines
Deal found 26/7C$ 1,046
Wed 28/1012:27 p.m.
MDW
-
YLW
2 stops12h 43m
Delta
Sat 31/107:55 p.m.
YLW
-
MDW
2 stops13h 52m
Delta
Deal found 25/7C$ 1,248
Tue 8/911:45 a.m.
MDW
-
YLW
2 stops26h 10m
Porter Airlines
Tue 15/912:50 p.m.
YLW
-
MDW
2 stops23h 45m
Porter Airlines
Deal found 25/7C$ 1,333
Tue 25/83:15 p.m.
MDW
-
YLW
2 stops22h 40m
Porter Airlines
Sat 29/812:50 p.m.
YLW
-
MDW
2 stops23h 45m
Porter Airlines
Deal found 26/7C$ 1,456
Thu 20/86:42 p.m.
MDW
-
YLW
2 stops27h 23m
WestJet
Mon 24/86:00 a.m.
YLW
-
MDW
2 stops10h 01m
WestJet
Deal found 22/7C$ 1,609
Tue 11/89:59 a.m.
MDW
-
YLW
2 stops11h 01m
WestJet
Sun 16/86:30 p.m.
YLW
-
MDW
2 stops19h 45m
WestJet
Deal found 22/7C$ 1,644
Thu 24/99:29 a.m.
MDW
-
YLW
2 stops14h 36m
WestJet
Mon 28/96:05 a.m.
YLW
-
MDW
2 stops14h 39m
WestJet
Deal found 26/7C$ 1,646
Tue 11/83:15 p.m.
MDW
-
YLW
2 stops22h 40m
Porter Airlines
Sun 16/812:50 p.m.
YLW
-
MDW
2 stops23h 45m
Porter Airlines
Deal found 26/7C$ 1,658
Wed 9/99:59 a.m.
MDW
-
YLW
2 stops11h 31m
WestJet
Wed 16/96:05 a.m.
YLW
-
MDW
2 stops10h 28m
WestJet
Deal found 26/7C$ 1,661
Wed 9/911:45 a.m.
MDW
-
YLW
2 stops26h 10m
Porter Airlines
Wed 16/912:50 p.m.
YLW
-
MDW
2 stops23h 45m
Porter Airlines
Deal found 26/7C$ 1,674

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 27 July 2026.

Round-trip from

C$ 1,046

One-way from

C$ 349
24/9-28/9
  • 24/9-28/9
  • 6 total stops
  • 30h 25m total
  • Chicago to Kelowna
Search Deals
31/8
  • 31/8
  • 3 total stops
  • 19h 25m 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 27 July 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

Thu 24/9

11:45 a.m.-11:50 p.m.

3 stops14h 05m

Kelowna

Mon 28/9

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

3 stops16h 20m

C$ 1,046

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 8/9

11:45 a.m.-11:55 a.m.

2 stops26h 10m

Kelowna

Tue 15/9

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

2 stops23h 45m

C$ 1,333

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 25/8

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

2 stops22h 40m

Kelowna

Sat 29/8

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

2 stops23h 45m

C$ 1,456

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 20/8

6:42 p.m.-8:05 p.m.

2 stops27h 23m

Kelowna

Mon 24/8

6:00 a.m.-6:01 p.m.

2 stops10h 01m

C$ 1,609

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 11/8

9:59 a.m.-7:00 p.m.

2 stops11h 01m

Kelowna

Sun 16/8

6:30 p.m.-4:15 p.m.

2 stops19h 45m

C$ 1,644
Quickest round-trip

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 21/8

1:25 p.m.-10:05 p.m.

2 stops10h 40m

Kelowna

Wed 26/8

6:05 a.m.-10:36 p.m.

2 stops14h 31m

C$ 1,646

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 24/9

9:29 a.m.-10:05 p.m.

2 stops14h 36m

Kelowna

Mon 28/9

6:05 a.m.-10:44 p.m.

2 stops14h 39m

C$ 1,646

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Wed 9/9

11:45 a.m.-11:55 a.m.

2 stops26h 10m

Kelowna

Wed 16/9

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

2 stops23h 45m

C$ 1,674
Cheapest one-way

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 31/8

11:50 a.m.-2:25 p.m.

2 stops28h 35m

C$ 356

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 30/8

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

3 stops37h 40m

C$ 390

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/7

Showing 1-10 of 12 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 26h 10m. 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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