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Cheap flights from Kelowna to Chicago Midway Airport from C$ 458

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 16/6. Fares are subject to change and may not be available on all flights or dates of travel.
YLW — MDW
17 Jun — 24 Jun1
1 adult

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 12 June 2025.

Round-trip from

C$ 541

Popular in

June

Cheapest in

December

Average price

C$ 852
Delta
  • Delta
  • 13/8-26/8
  • 4 total stops
  • 22h 29m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 118 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
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Find flight deals from Kelowna to Midway

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 12 June 2025.

Mon 16/611:30 p.m.YLW - MDW
2 stops10h 59mDelta
Tue 24/69:21 a.m.MDW - YLW
2 stops8h 04mDelta
Deal found 11/6C$ 458
Wed 13/87:00 a.m.YLW - MDW
2 stops8h 37mWestJet
Sun 24/812:43 p.m.MDW - YLW
2 stops11h 06mWestJet
Deal found 10/6C$ 978
Mon 16/611:30 p.m.YLW - MDW
1 stop14h 54mMultiple Airlines
Tue 24/69:40 a.m.MDW - YLW
2 stops14h 11mMultiple Airlines
Deal found 11/6C$ 1,055

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 12 June 2025.
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 13/8

5:55 a.m.-6:37 p.m.

2 stops10h 42m

Chicago Midway

Tue 26/8

1:43 p.m.-11:30 p.m.

2 stops11h 47m

C$ 541

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Wed 13/8

7:00 a.m.-5:37 p.m.

2 stops8h 37m

Chicago Midway

Sun 24/8

12:43 p.m.-9:49 p.m.

2 stops11h 06m

C$ 978

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

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.

Cheapflights Insights

Everything you need to know about your flight from Kelowna to Chicago Midway Airport

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 43.0 mm.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated 12 June 2025.
Delta
8.0
Very good
7,946 reviews
Check prices

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,946 reviews
Delta
8.0
Very good
7,946 reviews
Check prices

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
2,868 reviews
Delta
8.0
Very good
7,946 reviews
Check prices

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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.

  • What is the cheapest month to book a flight from Kelowna to Chicago Midway Airport?

    Currently, January is the cheapest month in which you can book a flight from Kelowna to Chicago Midway Airport (average of C$ 243). Flying from Kelowna to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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