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Cheap flights from Kelowna to Chicago Midway Airport from C$ 205

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 27/4. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — MDW
13 Apr — 20 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Kelowna to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Kelowna to Midway
Explore the most affordable flight options available from Kelowna to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 14 March 2026.

Fri 1/56:05 a.m.
YLW
-
MDW
2 stops9h 53m
Delta
Tue 5/51:24 p.m.
MDW
-
YLW
2 stops10h 41m
Delta
Deal found 8/3C$ 473
Mon 27/46:05 a.m.
YLW
-
MDW
2 stops9h 53m
Delta
Mon 4/51:24 p.m.
MDW
-
YLW
2 stops10h 41m
Delta
Deal found 12/3C$ 501
Tue 14/412:00 p.m.
YLW
-
MDW
1 stop20h 15m
Porter Airlines
Sun 19/44:05 p.m.
MDW
-
YLW
1 stop20h 58m
Porter Airlines
Deal found 10/3C$ 792
Fri 27/36:05 a.m.
YLW
-
MDW
2 stops13h 31m
Multiple Airlines
Sat 4/412:55 p.m.
MDW
-
YLW
1 stop24h 08m
Multiple Airlines
Deal found 10/3C$ 821
Sat 28/312:00 p.m.
YLW
-
MDW
1 stop25h 20m
Porter Airlines
Sat 4/412:55 p.m.
MDW
-
YLW
1 stop24h 08m
Porter Airlines
Deal found 10/3C$ 852
Tue 14/412:00 p.m.
YLW
-
MDW
1 stop20h 15m
Multiple Airlines
Sun 19/46:38 p.m.
MDW
-
YLW
2 stops18h 25m
Multiple Airlines
Deal found 10/3C$ 854
Sat 28/33:00 p.m.
YLW
-
MDW
2 stops22h 20m
Multiple Airlines
Sat 4/412:55 p.m.
MDW
-
YLW
1 stop24h 08m
Multiple Airlines
Deal found 10/3C$ 861
Fri 27/36:05 a.m.
YLW
-
MDW
2 stops13h 31m
Multiple Airlines
Fri 3/411:00 a.m.
MDW
-
YLW
1 stop26h 03m
Multiple Airlines
Deal found 10/3C$ 866

Find flight deals from Kelowna to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Kelowna (YLW) to Midway (MDW). 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 14 March 2026.

Round-trip from

C$ 493

One-way from

C$ 205

Popular in

July

Cheapest in

May

Average price

C$ 469
Delta
  • Delta
  • 1/5-5/5
  • 4 total stops
  • 20h 34m total
  • Kelowna to Chicago
Search Deals
27/4
  • 27/4
  • 2 total stops
  • 23h 59m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 104 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 43 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 Kelowna to Midway 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 14 March 2026.
Use the filters below to find and compare flights from Kelowna to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 1/5

6:05 a.m.-5:58 p.m.

2 stops9h 53m

Chicago Midway

Tue 5/5

1:24 p.m.-10:05 p.m.

2 stops10h 41m

C$ 473

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Mon 27/4

6:05 a.m.-5:58 p.m.

2 stops9h 53m

Chicago Midway

Mon 4/5

1:24 p.m.-10:05 p.m.

2 stops10h 41m

C$ 501

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 27/3

6:05 a.m.-9:36 p.m.

2 stops13h 31m

Chicago Midway

Fri 3/4

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

1 stop26h 03m

C$ 866

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 12/6

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

2 stops10h 26m

Chicago Midway

Sun 14/6

1:00 p.m.-10:05 p.m.

2 stops11h 05m

C$ 1,051

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 12/6

10:15 a.m.-9:40 a.m.

3 stops21h 25m

Chicago Midway

Sun 14/6

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

2 stops15h 25m

C$ 1,055

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 15/4

6:35 p.m.-9:56 a.m.

2 stops13h 21m

Chicago Midway

Mon 20/4

9:29 a.m.-6:26 p.m.

2 stops10h 57m

C$ 1,096

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sat 28/3

12:55 p.m.-5:54 p.m.

3 stops26h 59m

Chicago Midway

Sat 4/4

6:34 p.m.-11:03 a.m.

2 stops18h 29m

C$ 1,121
Cheapest one-way

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Mon 27/4

8:45 p.m.-7:31 p.m.

3 stops44h 46m

C$ 304

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sat 25/4

7:35 p.m.-10:19 p.m.

3 stops48h 44m

C$ 331

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 22/4

6:05 a.m.-3:04 p.m.

2 stops30h 59m

C$ 387

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

Showing 1-10 of 13 resultsSorted by cheapest first
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Best time to book a flight from Kelowna to Midway

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

    Located just 11.2 km from the city centre, Kelowna is the airport most travellers will use when flying to Chicago Midway from Kelowna. Booking flights from Kelowna (YLW) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 0 different airlines.

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

    Departing from Kelowna to Chicago Midway Airport will take you 9h 53m. Airlines will cover a distance of 2586 km.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Kelowna to Midway 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

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Why should you use Cheapflights to find cheap flight tickets from Kelowna to Midway?

Cheapflights simply makes it quick and affordable to book flights from Kelowna to Midway by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Kelowna to Midway with no change fees?

Yes, we can. To see specific flights from Kelowna to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Kelowna to Midway become cheaper?

Of course! You can now track prices for flights from Kelowna to Midway and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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