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Cheap flights from Kelowna to Chicago Midway Airport from C$ 331

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 18/5. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — MDW
23 May — 30 May1
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 23 April 2026.

Thu 24/96:05 a.m.
YLW
-
MDW
2 stops10h 26m
Delta
Mon 28/91:00 p.m.
MDW
-
YLW
2 stops12h 50m
Delta
Deal found 19/4C$ 826
Sat 25/47:55 p.m.
YLW
-
MDW
2 stops12h 01m
WestJet
Sun 3/59:27 a.m.
MDW
-
YLW
2 stops14h 38m
WestJet
Deal found 18/4C$ 1,087
Sun 7/66:05 a.m.
YLW
-
MDW
2 stops10h 13m
WestJet
Sun 14/61:16 p.m.
MDW
-
YLW
2 stops10h 49m
WestJet
Deal found 22/4C$ 1,094
Wed 24/612:50 p.m.
YLW
-
MDW
2 stops18h 50m
Multiple Airlines
Mon 29/61:16 p.m.
MDW
-
YLW
3 stops24h 39m
Multiple Airlines
Deal found 19/4C$ 1,095
Thu 13/85:05 a.m.
YLW
-
MDW
2 stops11h 00m
WestJet
Sun 16/810:35 a.m.
MDW
-
YLW
2 stops10h 50m
WestJet
Deal found 23/4C$ 1,117
Sat 2/55:55 a.m.
YLW
-
MDW
2 stops34h 41m
Delta
Tue 5/51:24 p.m.
MDW
-
YLW
2 stops12h 26m
Delta
Deal found 18/4C$ 1,135
Thu 25/612:50 p.m.
YLW
-
MDW
2 stops18h 50m
Multiple Airlines
Mon 29/69:17 a.m.
MDW
-
YLW
3 stops28h 38m
Multiple Airlines
Deal found 19/4C$ 1,151
Fri 24/47:35 p.m.
YLW
-
MDW
2 stops12h 21m
WestJet
Sun 3/59:27 a.m.
MDW
-
YLW
2 stops14h 38m
WestJet
Deal found 20/4C$ 1,221

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 23 April 2026.

Round-trip from

C$ 826

One-way from

C$ 331

Popular in

July

Cheapest in

May

Average price

C$ 654
Delta
  • Delta
  • 24/9-28/9
  • 4 total stops
  • 23h 16m total
  • Kelowna to Chicago
Search Deals
18/5
  • 18/5
  • 2 total stops
  • 25h 27m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 128 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 23 April 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

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 24/9

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

2 stops10h 26m

Chicago Midway

Mon 28/9

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

2 stops12h 50m

C$ 826

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 24/6

5:05 a.m.-6:18 p.m.

2 stops11h 13m

Chicago Midway

Mon 29/6

1:16 p.m.-10:05 p.m.

2 stops10h 49m

C$ 1,087

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 25/6

5:05 a.m.-6:18 p.m.

2 stops11h 13m

Chicago Midway

Mon 29/6

7:16 p.m.-2:35 p.m.

2 stops21h 19m

C$ 1,087
Quickest round-trip

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sun 7/6

6:05 a.m.-6:18 p.m.

2 stops10h 13m

Chicago Midway

Sun 14/6

1:16 p.m.-10:05 p.m.

2 stops10h 49m

C$ 1,094

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 24/6

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

2 stops10h 26m

Chicago Midway

Sun 28/6

9:54 a.m.-10:05 p.m.

2 stops14h 11m

C$ 1,414

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 13/8

12:50 p.m.-8:42 a.m.

3 stops17h 52m

Chicago Midway

Sun 16/8

9:30 a.m.-9:52 p.m.

2 stops14h 22m

C$ 1,421
Cheapest one-way

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Mon 18/5

6:35 p.m.-10:02 p.m.

2 stops25h 27m

C$ 331
Quickest one-way

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 2/6

3:10 p.m.-11:09 a.m.

3 stops17h 59m

C$ 348

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 4/6

8:45 p.m.-10:02 p.m.

3 stops47h 17m

C$ 384

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 15/7

8:45 p.m.-10:11 p.m.

3 stops47h 26m

C$ 453

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/4

Sorted by cheapest first

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 10h 26m. Airlines will cover a distance of 2586 km. Both multi-stop and direct flights can be found to your destination and back.

  • 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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When you search for this flight from Kelowna to Midway, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

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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