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Cheap flights from Windsor, ON to Kissimmee from C$ 284

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 14/4. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — MCO
2 Apr — 9 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Windsor to Kissimmee

Enter your travel dates to find the best prices.

Cheapest flights from Windsor to Kissimmee
Explore the most affordable flight options available from Windsor to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 3 March 2026.

Tue 24/39:40 a.m.
YQG
-
MCO
1 stop5h 25m
Air Canada
Mon 30/312:05 p.m.
MCO
-
YQG
1 stop7h 04m
Air Canada
Deal found 27/2C$ 502
Wed 15/47:45 p.m.
YQG
-
MCO
1 stop15h 21m
Air Canada
Wed 22/48:30 a.m.
MCO
-
YQG
2 stops10h 39m
Air Canada
Deal found 27/2C$ 514
Tue 14/49:45 a.m.
YQG
-
MCO
2 stops13h 01m
Air Canada
Tue 21/48:30 a.m.
MCO
-
YQG
2 stops10h 39m
Air Canada
Deal found 28/2C$ 541
Thu 26/37:50 p.m.
YQG
-
MCO
1 stop15h 25m
Air Canada
Thu 2/412:05 p.m.
MCO
-
YQG
1 stop7h 04m
Air Canada
Deal found 2/3C$ 547
Thu 26/37:50 p.m.
YQG
-
MCO
1 stop13h 30m
Air Canada
Fri 3/48:30 a.m.
MCO
-
YQG
2 stops10h 39m
Air Canada
Deal found 2/3C$ 559
Fri 17/49:45 a.m.
YQG
-
MCO
1 stop14h 01m
Air Canada
Mon 20/48:30 a.m.
MCO
-
YQG
2 stops10h 39m
Air Canada
Deal found 27/2C$ 574
Sat 16/510:05 a.m.
YQG
-
MCO
2 stops8h 46m
Air Canada
Sat 23/59:55 p.m.
MCO
-
YQG
1 stop11h 29m
Air Canada
Deal found 3/3C$ 577

Find flight deals from Windsor to Kissimmee

Keep the following information in mind while searching for Windsor to Kissimmee flight deals. Data was last updated 3 March 2026.

Round-trip from

C$ 502

One-way from

C$ 284

Popular in

June

Cheapest in

April

Average price

C$ 599
Air Canada
  • Air Canada
  • 24/3-30/3
  • 2 total stops
  • 12h 29m total
  • Windsor to Kissimmee
Search Deals
14/4
  • 14/4
  • 2 total stops
  • 10h 06m total
  • Windsor to Kissimmee
Search Deals
Highest demand for flights based on searches. 33% potential increase in price (C$ 438 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease (C$ 92 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 Windsor to Kissimmee 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 3 March 2026.
Use the filters below to find and compare flights from Windsor to Kissimmee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Wed 15/4

7:45 p.m.-11:06 a.m.

1 stop15h 21m

Orlando

Wed 22/4

8:30 a.m.-7:09 p.m.

2 stops10h 39m

C$ 514

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Sat 28/3

7:50 p.m.-11:06 a.m.

1 stop15h 16m

Orlando

Sat 4/4

8:45 p.m.-9:04 a.m.

1 stop12h 19m

C$ 649

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Sun 22/3

7:50 p.m.-12:32 p.m.

2 stops16h 42m

Orlando

Sat 28/3

10:00 p.m.-9:04 a.m.

1 stop11h 04m

C$ 761

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Sat 28/3

7:35 a.m.-8:10 p.m.

2 stops12h 35m

Orlando

Sat 4/4

8:45 p.m.-7:33 p.m.

2 stops22h 48m

C$ 871

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Mon 4/5

4:30 p.m.-12:45 p.m.

2 stops20h 15m

Orlando

Mon 11/5

8:45 p.m.-3:46 p.m.

1 stop19h 01m

C$ 891

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Sat 28/3

7:35 a.m.-12:58 p.m.

2 stops29h 23m

Orlando

Wed 1/4

1:00 p.m.-7:33 p.m.

2 stops30h 33m

C$ 931

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Thu 26/3

7:35 a.m.-7:48 p.m.

2 stops12h 13m

Orlando

Sat 4/4

8:45 p.m.-7:33 p.m.

2 stops22h 48m

C$ 943

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Sun 15/3

7:50 p.m.-9:20 a.m.

1 stop13h 30m

Orlando

Thu 19/3

9:26 a.m.-7:14 p.m.

2 stops9h 48m

C$ 954

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Thu 26/3

7:35 a.m.-7:48 p.m.

2 stops12h 13m

Orlando

Sun 5/4

8:45 p.m.-7:33 p.m.

2 stops22h 48m

C$ 962

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Sat 11/4

7:35 a.m.-8:45 p.m.

2 stops13h 10m

C$ 294

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/2

Showing 1-10 of 18 resultsSorted by cheapest first
1
2

Best time to book a flight from Windsor to Kissimmee

Have a flexible travel schedule? Discover the best time to fly to Kissimmee from Windsor 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 Windsor to Kissimmee
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Kissimmee

Get insights into the airlines that provide service to Kissimmee. 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 Kissimmee. Reviews last updated 3 March 2026.
Check out reviews from past customers who have flown with Air Canada from Windsor to Kissimmee to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
10,771 reviews
Check prices

Entertainment

6.8

Overall

7.1

Comfort

7.1

Crew

7.8

Food

6.3

Boarding

7.3

Reviews

1 / 20
4.0
Okay

Sugith,Jan 2026

YSB - YYZ

Left 2 hours late. Stuck on plane for an hour after boarding before take off.
Air Canada
7.1
Good
10,771 reviews
Air Canada
7.1
Good
10,771 reviews
Check prices

Entertainment

6.8

Overall

7.1

Comfort

7.1

Crew

7.8

Food

6.3

Boarding

7.3

Reviews

1 / 20
4.0
Okay

Sugith,Jan 2026

YSB - YYZ

Left 2 hours late. Stuck on plane for an hour after boarding before take off.

Related info for your journey

Find useful and relevant information for your journey from Windsor to Kissimmee. 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 Windsor to Kissimmee?

    For a flight from Windsor to Kissimmee, you will be flying from Windsor. Windsor (YQG) is just 8.0 km from the centre of the city. Windsor is the only Windsor airport and it handles 0 outbound flights to Kissimmee per day. 1 airline has flights to Kissimmee from Windsor on a regular basis.

  • How long is the flight from Windsor, Ontario to Kissimmee?

    For as low as C$ 649, Air Canada can have you in Kissimmee from Windsor, Ontario in 15h 16m. Airlines will cover a distance of 1545 km.

  • Can I find deals for flights from Windsor to Kissimmee that include hotel bookings?

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

  • How can I find direct flights from Windsor to Kissimmee?

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

  • Can I find deals for business class flights from Windsor to Kissimmee?

    Yes. Cheapflights offers flight deals from Windsor to Kissimmee 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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Alternative routes for Windsor to Kissimmee

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Top airline flying from Windsor to Kissimmee

Discover the top airline that operate flights from Windsor to Kissimmee. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 3 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 418AverageC$ 640FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Windsor to Kissimmee?

When you search for this flight from Windsor to Kissimmee, 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 Windsor to Kissimmee?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Windsor to Kissimmee for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Windsor to Kissimmee with no change fees?

Need flexible booking options for your flight to Kissimmee from Windsor? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Windsor to Kissimmee become cheaper?

Not ready to book yet? You can track prices for flights from Windsor to Kissimmee on Cheapflights with our Price Alert feature and get notified when better prices are available.

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