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Cheap flights from Kelowna to Chicago Midway Airport from C$ 168

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 25/2. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — MDW
10 Feb — 17 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap 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 11 January 2026.

Round-trip from

C$ 790

One-way from

C$ 168

Popular in

March

Cheapest in

June
Delta
  • Delta
  • 11/2-17/2
  • 4 total stops
  • 62h 26m total
  • Kelowna to Chicago
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25/2
  • 25/2
  • 2 total stops
  • 29h 41m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 115 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (C$ 59 potential savings vs. average RT price).
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Find 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 11 January 2026.

Wed 11/28:55 a.m.YLW - MDW
2 stops31h 45mDelta
Tue 17/29:50 a.m.MDW - YLW
2 stops30h 41mDelta
Deal found 11/1C$ 790
Wed 11/28:55 a.m.YLW - MDW
2 stops31h 45mDelta
Fri 20/26:00 a.m.MDW - YLW
2 stops18h 41mDelta
Deal found 11/1C$ 850
Wed 11/28:55 a.m.YLW - MDW
2 stops22h 11mDelta
Wed 18/21:49 p.m.MDW - YLW
2 stops12h 04mDelta
Deal found 11/1C$ 872
Wed 11/28:55 a.m.YLW - MDW
2 stops26h 10mDelta
Mon 16/21:49 p.m.MDW - YLW
2 stops12h 04mDelta
Deal found 11/1C$ 888
Sat 28/27:55 p.m.YLW - MDW
2 stops14h 04mDelta
Mon 2/31:49 p.m.MDW - YLW
2 stops12h 04mDelta
Deal found 9/1C$ 910
Tue 10/28:55 a.m.YLW - MDW
2 stops31h 41mDelta
Tue 17/21:49 p.m.MDW - YLW
2 stops26h 42mDelta
Deal found 11/1C$ 983
Tue 10/28:55 a.m.YLW - MDW
2 stops26h 11mDelta
Thu 19/212:45 p.m.MDW - YLW
2 stops35h 56mDelta
Deal found 11/1C$ 1,013
Tue 10/28:55 a.m.YLW - MDW
2 stops22h 13mDelta
Wed 18/21:49 p.m.MDW - YLW
2 stops12h 04mDelta
Deal found 11/1C$ 1,066
Mon 23/28:55 a.m.YLW - MDW
2 stops26h 10mWestJet
Tue 24/27:20 p.m.MDW - YLW
2 stops25h 06mWestJet
Deal found 10/1C$ 1,078
Tue 10/28:55 a.m.YLW - MDW
2 stops31h 41mDelta
Mon 16/21:49 p.m.MDW - YLW
2 stops12h 04mDelta
Deal found 11/1C$ 1,081

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 11 January 2026.
Use the filters below to find and compare flights from Kelowna to Chicago Midway Airport that are best for you.

Fly from

Kelowna

Fly to

Midway

Route

Depart

Return

Price

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 11/2

8:55 a.m.-6:40 p.m.

2 stops31h 45m

Chicago Midway

Tue 17/2

9:50 a.m.-2:31 p.m.

2 stops30h 41m

C$ 790

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 11/2

8:55 a.m.-1:05 p.m.

2 stops26h 10m

Chicago Midway

Thu 19/2

12:45 p.m.-10:41 p.m.

2 stops35h 56m

C$ 821

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 11/2

8:55 a.m.-6:40 p.m.

2 stops31h 45m

Chicago Midway

Fri 20/2

6:00 a.m.-10:41 p.m.

2 stops18h 41m

C$ 850

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 11/2

8:55 a.m.-9:06 a.m.

2 stops22h 11m

Chicago Midway

Wed 18/2

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

2 stops12h 04m

C$ 872

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 11/2

8:55 a.m.-1:05 p.m.

2 stops26h 10m

Chicago Midway

Mon 16/2

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

2 stops12h 04m

C$ 888

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Sat 28/2

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

2 stops14h 04m

Chicago Midway

Mon 2/3

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

2 stops12h 04m

C$ 910

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 10/2

8:55 a.m.-6:36 p.m.

2 stops31h 41m

Chicago Midway

Tue 17/2

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

2 stops26h 42m

C$ 983

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 10/2

8:55 a.m.-1:06 p.m.

2 stops26h 11m

Chicago Midway

Thu 19/2

12:45 p.m.-10:41 p.m.

2 stops35h 56m

C$ 1,013

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 10/2

8:55 a.m.-9:08 a.m.

2 stops22h 13m

Chicago Midway

Fri 20/2

6:00 a.m.-10:41 p.m.

2 stops18h 41m

C$ 1,043

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 10/2

8:55 a.m.-9:08 a.m.

2 stops22h 13m

Chicago Midway

Wed 18/2

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

2 stops12h 04m

C$ 1,066

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 21 results
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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 31h 45m. 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.

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

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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.

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