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Cheap flights from Chicago Midway Airport to Kelowna from C$ 264

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 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YLW
26 Feb — 5 Mar1
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 January 2026.

Fri 20/211:05 a.m.
MDW
-
YLW
3 stops14h 48m
Multiple Airlines
Tue 24/210:20 a.m.
YLW
-
MDW
3 stops21h 50m
Multiple Airlines
Deal found 25/1C$ 674
Mon 2/26:54 p.m.
MDW
-
YLW
2 stops30h 19m
Multiple Airlines
Sat 7/25:55 p.m.
YLW
-
MDW
3 stops19h 25m
Multiple Airlines
Deal found 25/1C$ 867
Wed 25/21:49 p.m.
MDW
-
YLW
2 stops12h 04m
Delta
Mon 2/37:55 p.m.
YLW
-
MDW
2 stops14h 04m
Delta
Deal found 24/1C$ 1,179
Sun 1/210:48 a.m.
MDW
-
YLW
2 stops13h 00m
WestJet
Thu 5/24:00 p.m.
YLW
-
MDW
2 stops24h 36m
WestJet
Deal found 24/1C$ 1,260
Thu 26/210:49 a.m.
MDW
-
YLW
2 stops12h 59m
WestJet
Sun 1/34:00 p.m.
YLW
-
MDW
2 stops24h 40m
WestJet
Deal found 27/1C$ 1,272
Mon 2/39:50 a.m.
MDW
-
YLW
2 stops48h 10m
WestJet
Wed 4/310:10 a.m.
YLW
-
MDW
2 stops30h 30m
WestJet
Deal found 25/1C$ 1,419
Fri 6/39:50 a.m.
MDW
-
YLW
2 stops10h 42m
WestJet
Sat 14/37:55 p.m.
YLW
-
MDW
2 stops12h 01m
WestJet
Deal found 24/1C$ 1,564
Sat 7/311:45 a.m.
MDW
-
YLW
2 stops14h 08m
Delta
Sat 14/37:55 p.m.
YLW
-
MDW
2 stops14h 07m
Delta
Deal found 24/1C$ 2,116
Fri 13/310:45 a.m.
MDW
-
YLW
2 stops13h 03m
WestJet
Fri 20/35:20 a.m.
YLW
-
MDW
2 stops10h 02m
WestJet
Deal found 27/1C$ 3,186

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 January 2026.

Round-trip from

C$ 757

One-way from

C$ 264

Popular in

October

Cheapest in

July

Average price

C$ 582
28/2-6/3
  • 28/2-6/3
  • 3 total stops
  • 31h 25m total
  • Chicago to Kelowna
Search Deals
4/3
  • 4/3
  • 2 total stops
  • 23h 05m total
  • Chicago to Kelowna
Search Deals
Highest demand for flights based on searches. 26% potential increase in price (C$ 370 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease (C$ 111 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 27 January 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Kelowna that are best for you.

Fly from

Midway

Fly to

Kelowna

Route

Depart

Return

Price

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 20/2

11:05 a.m.-10:41 p.m.

1 stop13h 36m

Kelowna

Tue 24/2

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

3 stops21h 50m

C$ 674

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Wed 25/2

1:49 p.m.-11:53 p.m.

2 stops12h 04m

Kelowna

Mon 2/3

7:55 p.m.-11:59 a.m.

2 stops14h 04m

C$ 1,179

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 26/2

10:49 a.m.-9:48 p.m.

2 stops12h 59m

Kelowna

Tue 3/3

2:15 p.m.-6:40 p.m.

2 stops26h 25m

C$ 1,260

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 26/2

10:49 a.m.-9:48 p.m.

2 stops12h 59m

Kelowna

Sun 1/3

4:00 p.m.-6:40 p.m.

2 stops24h 40m

C$ 1,272

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 24/2

1:49 p.m.-2:31 p.m.

2 stops26h 42m

Kelowna

Sun 1/3

7:35 p.m.-9:54 a.m.

2 stops12h 19m

C$ 1,284

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 2/3

9:50 a.m.-8:00 a.m.

2 stops48h 10m

Kelowna

Wed 4/3

10:10 a.m.-6:40 p.m.

2 stops30h 30m

C$ 1,419

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Wed 4/3

11:00 a.m.-8:05 a.m.

2 stops23h 05m

C$ 264

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Wed 4/3

11:00 a.m.-11:03 a.m.

1 stop26h 03m

C$ 323

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 15/2

4:15 p.m.-3:26 p.m.

3 stops49h 11m

C$ 360

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 13/3

11:00 a.m.-8:15 a.m.

3 stops23h 15m

C$ 450

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/1

Showing 1-10 of 11 results
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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 12h 04m. 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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