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Cheap flights from Chicago Midway Airport to Kelowna from C$ 434

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 23/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YLW
10 Jul — 17 Jul1
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 June 2026.

Tue 7/73:20 p.m.
MDW
-
YLW
2 stops22h 35m
Porter Airlines
Thu 9/710:50 p.m.
YLW
-
MDW
1 stop13h 45m
Porter Airlines
Deal found 9/6C$ 803
Sat 19/91:14 p.m.
MDW
-
YLW
2 stops10h 51m
Delta
Tue 22/96:05 a.m.
YLW
-
MDW
2 stops10h 28m
Delta
Deal found 8/6C$ 814
Tue 7/710:25 a.m.
MDW
-
YLW
2 stops15h 25m
Multiple Airlines
Thu 9/712:50 p.m.
YLW
-
MDW
2 stops18h 50m
Multiple Airlines
Deal found 9/6C$ 918
Tue 7/710:25 a.m.
MDW
-
YLW
2 stops15h 05m
Multiple Airlines
Fri 10/712:50 p.m.
YLW
-
MDW
2 stops18h 50m
Multiple Airlines
Deal found 9/6C$ 927
Mon 20/73:20 p.m.
MDW
-
YLW
3 stops24h 00m
Multiple Airlines
Mon 27/71:55 p.m.
YLW
-
MDW
3 stops22h 40m
Multiple Airlines
Deal found 8/6C$ 1,181
Sun 2/81:18 p.m.
MDW
-
YLW
2 stops34h 34m
Multiple Airlines
Thu 6/812:50 p.m.
YLW
-
MDW
3 stops18h 27m
Multiple Airlines
Deal found 7/6C$ 1,330
Sun 5/77:16 p.m.
MDW
-
YLW
2 stops28h 36m
Multiple Airlines
Sun 12/712:50 p.m.
YLW
-
MDW
2 stops18h 50m
Multiple Airlines
Deal found 7/6C$ 1,351

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 June 2026.

Round-trip from

C$ 803

One-way from

C$ 434
Porter Airlines
  • Porter Airlines
  • 7/7-9/7
  • 3 total stops
  • 36h 20m total
  • Chicago to Kelowna
Search Deals
23/7
  • 23/7
  • 2 total stops
  • 28h 24m 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 10 June 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
Quickest round-trip

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sat 19/9

1:14 p.m.-10:05 p.m.

2 stops10h 51m

Kelowna

Tue 22/9

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

2 stops10h 28m

C$ 814

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 7/7

10:25 a.m.-11:30 p.m.

2 stops15h 05m

Kelowna

Fri 10/7

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

2 stops18h 50m

C$ 927

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 7/7

1:18 p.m.-11:55 a.m.

3 stops24h 37m

Kelowna

Thu 9/7

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

2 stops18h 50m

C$ 1,017

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 5/7

7:16 p.m.-9:52 p.m.

2 stops28h 36m

Kelowna

Sun 12/7

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

2 stops18h 50m

C$ 1,351

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 2/8

1:18 p.m.-9:52 p.m.

2 stops34h 34m

Kelowna

Thu 6/8

10:50 p.m.-6:33 p.m.

2 stops17h 43m

C$ 1,383

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 11/8

7:25 p.m.-7:00 p.m.

2 stops25h 35m

Kelowna

Sun 16/8

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

2 stops10h 01m

C$ 1,534

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sat 1/8

1:18 p.m.-11:50 p.m.

2 stops12h 32m

Kelowna

Wed 5/8

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

2 stops10h 01m

C$ 1,597
Cheapest one-way
Quickest one-way

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 23/7

10:25 a.m.-9:45 a.m.

3 stops25h 20m

C$ 466

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 9/7

10:25 a.m.-9:45 a.m.

3 stops25h 20m

C$ 476

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 9/7

3:20 p.m.-11:55 a.m.

2 stops46h 35m

C$ 545

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/6

Sorted by cheapest first

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 51m. 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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