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Cheap flights from Windsor, ON to Kissimmee from C$ 273

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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — MCO
18 Feb — 25 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Windsor to Kissimmee

Keep the following information in mind while searching for Windsor to Kissimmee flight deals. Data was last updated 19 January 2026.

Round-trip from

C$ 483

One-way from

C$ 273

Popular in

June

Cheapest in

April

Average price

C$ 743
Air Canada
  • Air Canada
  • 4/3-11/3
  • 2 total stops
  • 12h 24m total
  • Windsor to Kissimmee
Search Deals
Air Canada
  • Air Canada
  • 3/3
  • 1 total stop
  • 5h 20m total
  • Windsor to Kissimmee
Search Deals
Highest demand for flights based on searches. 32% potential increase in price (C$ 438 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease (C$ 94 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Find 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 19 January 2026.

Wed 4/39:45 a.m.
YQG
-
MCO
1 stop5h 20m
Air Canada
Wed 11/312:10 p.m.
MCO
-
YQG
1 stop7h 04m
Air Canada
Deal found 18/1C$ 483
Tue 7/49:45 a.m.
YQG
-
MCO
1 stop5h 11m
Air Canada
Thu 9/48:30 a.m.
MCO
-
YQG
2 stops10h 39m
Air Canada
Deal found 16/1C$ 499
Tue 18/84:05 p.m.
YQG
-
MCO
1 stop7h 42m
Air Canada
Thu 27/87:00 a.m.
MCO
-
YQG
1 stop12h 07m
Air Canada
Deal found 16/1C$ 516
Sun 25/17:50 p.m.
YQG
-
MCO
1 stop13h 30m
Air Canada
Mon 26/110:00 p.m.
MCO
-
YQG
1 stop11h 04m
Air Canada
Deal found 17/1C$ 550
Thu 29/19:45 a.m.
YQG
-
MCO
1 stop11h 15m
Air Canada
Mon 2/210:00 p.m.
MCO
-
YQG
1 stop11h 04m
Air Canada
Deal found 17/1C$ 573

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 19 January 2026.
Use the filters below to find and compare flights from Windsor to Kissimmee that are best for you.

Fly from

Windsor

Fly to

Kissimmee

Route

Depart

Return

Price

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Wed 4/3

9:45 a.m.-3:05 p.m.

1 stop5h 20m

Orlando

Wed 11/3

12:10 p.m.-7:14 p.m.

1 stop7h 04m

C$ 483

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Tue 7/4

9:45 a.m.-2:56 p.m.

1 stop5h 11m

Orlando

Thu 9/4

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

2 stops10h 39m

C$ 499

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Thu 29/1

9:45 a.m.-9:00 p.m.

1 stop11h 15m

Orlando

Mon 2/2

8:30 a.m.-7:14 p.m.

2 stops10h 44m

C$ 575

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Sat 28/3

9:45 a.m.-11:50 p.m.

1 stop14h 05m

Orlando

Fri 3/4

8:00 a.m.-7:09 p.m.

1 stop11h 09m

C$ 590

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Thu 19/2

9:45 a.m.-8:29 p.m.

2 stops10h 44m

Orlando

Fri 27/2

7:00 a.m.-7:14 p.m.

2 stops12h 14m

C$ 608

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Tue 3/3

9:45 a.m.-3:05 p.m.

1 stop5h 20m

C$ 273

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Tue 3/3

7:35 a.m.-5:57 p.m.

2 stops10h 22m

C$ 289

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Fri 27/3

7:50 p.m.-11:15 a.m.

1 stop15h 25m

C$ 360

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Fri 27/3

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

2 stops12h 13m

C$ 385

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Mon 2/3

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

2 stops29h 23m

C$ 490

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/1

Showing 1-10 of 13 results
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 19 January 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
10,635 reviews
Check prices

Boarding

7.3

Comfort

7.1

Entertainment

6.8

Food

6.3

Overall

7.1

Crew

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

YYZ - LAS

It's was great and the crew are very nice, captain has a smooth land on the runway 👍
Air Canada
7.1
Good
10,635 reviews
Air Canada
7.1
Good
10,635 reviews
Check prices

Boarding

7.3

Comfort

7.1

Entertainment

6.8

Food

6.3

Overall

7.1

Crew

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

YYZ - LAS

It's was great and the crew are very nice, captain has a smooth land on the runway 👍

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$ 483, Air Canada can have you in Kissimmee from Windsor, Ontario in 5h 20m. 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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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 19 January 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 360AverageC$ 634FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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.

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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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