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Cheap flights from Windsor, ON to Kissimmee from C$ 335

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 15/7. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — MCO
18 May — 25 May1
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 18 April 2026.

Tue 8/129:45 a.m.
YQG
-
MCO
1 stop5h 20m
Air Canada
Fri 11/1212:10 p.m.
MCO
-
YQG
1 stop7h 04m
Air Canada
Deal found 17/4C$ 553
Wed 20/54:05 p.m.
YQG
-
MCO
1 stop7h 41m
Air Canada
Sat 23/59:55 p.m.
MCO
-
YQG
1 stop11h 29m
Air Canada
Deal found 17/4C$ 601
Tue 8/129:45 a.m.
YQG
-
MCO
1 stop5h 20m
Air Canada
Wed 9/1212:10 p.m.
MCO
-
YQG
1 stop7h 04m
Air Canada
Deal found 13/4C$ 614
Sun 10/54:05 p.m.
YQG
-
MCO
1 stop7h 41m
Air Canada
Tue 12/57:00 a.m.
MCO
-
YQG
1 stop12h 09m
Air Canada
Deal found 13/4C$ 643
Sun 31/510:05 a.m.
YQG
-
MCO
2 stops13h 11m
Air Canada
Sun 7/68:40 p.m.
MCO
-
YQG
1 stop12h 44m
Air Canada
Deal found 16/4C$ 659

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 18 April 2026.

Round-trip from

C$ 601

One-way from

C$ 335

Popular in

October

Cheapest in

April

Average price

C$ 436
Air Canada
  • Air Canada
  • 20/5-23/5
  • 2 total stops
  • 19h 10m total
  • Windsor to Kissimmee
Search Deals
Air Canada
  • Air Canada
  • 14/7
  • 1 total stop
  • 7h 42m total
  • Windsor to Kissimmee
Search Deals
Highest demand for flights based on searches. 19% potential increase in price (C$ 294 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 14% potential price decrease (C$ 148 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 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 18 April 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

Cheapest round-trip

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Wed 20/5

4:05 p.m.-11:46 p.m.

1 stop7h 41m

Orlando

Sat 23/5

9:55 p.m.-9:24 a.m.

1 stop11h 29m

C$ 601
Quickest round-trip

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Sun 31/5

10:05 a.m.-3:46 p.m.

1 stop5h 41m

Orlando

Sun 7/6

8:40 p.m.-9:24 a.m.

1 stop12h 44m

C$ 647

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Fri 3/7

10:05 a.m.-11:12 p.m.

2 stops13h 07m

Orlando

Sun 5/7

7:00 a.m.-7:07 p.m.

1 stop12h 07m

C$ 826

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Wed 13/5

10:05 a.m.-6:30 p.m.

2 stops8h 25m

Orlando

Wed 20/5

9:02 a.m.-7:09 p.m.

2 stops10h 07m

C$ 856

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Tue 12/5

4:05 p.m.-11:46 p.m.

1 stop7h 41m

Orlando

Tue 19/5

9:55 p.m.-9:24 a.m.

1 stop11h 29m

C$ 865

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Sat 2/5

10:05 a.m.-11:16 p.m.

2 stops13h 11m

Orlando

Mon 4/5

9:02 a.m.-7:09 p.m.

2 stops10h 07m

C$ 880

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Sun 10/5

10:05 a.m.-11:16 p.m.

2 stops13h 11m

Orlando

Tue 12/5

7:15 a.m.-7:09 p.m.

2 stops11h 54m

C$ 881
Cheapest one-way

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Wed 15/7

4:05 p.m.-11:47 p.m.

1 stop7h 42m

C$ 335

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Sat 30/5

4:30 p.m.-10:40 a.m.

2 stops18h 10m

C$ 353

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Fri 29/5

4:05 p.m.-11:46 p.m.

1 stop7h 41m

C$ 368

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/4

Showing 1-10 of 16 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 18 April 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
10,935 reviews
Check prices

Entertainment

6.8

Crew

7.8

Overall

7.1

Boarding

7.3

Comfort

7.1

Food

6.3

Reviews

1 / 20
6.0
Good

Thomas,Apr 2026

YYZ - LHR

Food is sub par. I travel a lot and AC food is not good
Air Canada
7.1
Good
10,935 reviews
Air Canada
7.1
Good
10,935 reviews
Check prices

Entertainment

6.8

Crew

7.8

Overall

7.1

Boarding

7.3

Comfort

7.1

Food

6.3

Reviews

1 / 20
6.0
Good

Thomas,Apr 2026

YYZ - LHR

Food is sub par. I travel a lot and AC food is not good

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$ 601, Air Canada can have you in Kissimmee from Windsor, Ontario in 7h 41m. 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 18 April 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 357AverageC$ 731FlexibilityNo 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?

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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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