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Cheap flights from Windsor, ON to Kissimmee from C$ 274

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 17/9. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — MCO
6 Aug — 13 Aug1
1 adult

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 1 August 2025.

Round-trip from

C$ 440

One-way from

C$ 275

Popular in

July

Cheapest in

April

Average price

C$ 573
Air Canada
  • Air Canada
  • 13/9-20/9
  • 3 total stops
  • 21h 14m total
  • Windsor to Kissimmee
Search Deals
Air Canada
  • Air Canada
  • 13/9
  • 2 total stops
  • 7h 57m total
  • Windsor to Kissimmee
Search Deals
Highest demand for flights based on searches. 21% potential increase in price (C$ 259 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 46 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

Find flight deals from Windsor to Kissimmee

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 1 August 2025.

Sat 13/93:55 p.m.YQG - MCO
2 stops7h 57mAir Canada
Sat 20/98:05 p.m.MCO - YQG
1 stop13h 17mAir Canada
Deal found 29/7C$ 440
Mon 15/98:40 a.m.YQG - MCO
3 stops24h 57mMultiple Airlines
Mon 22/99:54 a.m.MCO - YQG
2 stops10h 56mMultiple Airlines
Deal found 1/8C$ 731
Sun 14/98:50 a.m.YQG - MCO
2 stops10h 51mPorter Airlines
Sun 21/91:45 p.m.MCO - YQG
2 stops31h 05mPorter Airlines
Deal found 31/7C$ 890
Mon 4/87:45 p.m.YQG - MCO
1 stop21h 33mWestJet
Wed 6/86:30 p.m.MCO - YQG
2 stops24h 25mWestJet
Deal found 31/7C$ 2,675

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 1 August 2025.
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

Sat 13/9

3:55 p.m.-11:52 p.m.

2 stops7h 57m

Orlando

Sat 20/9

8:05 p.m.-9:22 a.m.

1 stop13h 17m

C$ 440

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Mon 15/9

8:40 a.m.-9:37 a.m.

3 stops24h 57m

Orlando

Mon 22/9

9:54 a.m.-8:50 p.m.

2 stops10h 56m

C$ 731

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Sun 14/9

8:50 a.m.-7:41 p.m.

2 stops10h 51m

Orlando

Sun 21/9

1:45 p.m.-8:50 p.m.

2 stops31h 05m

C$ 890

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Wed 17/9

3:55 p.m.-11:48 p.m.

1 stop7h 53m

C$ 274

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Sat 13/9

8:50 a.m.-7:55 a.m.

3 stops23h 05m

C$ 392

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Sun 14/9

8:50 a.m.-7:41 p.m.

2 stops10h 51m

C$ 425

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/8

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

What is the cheapest month to book a flight from Windsor, Ontario to Kissimmee?

Currently, June is the cheapest month in which you can book a flight from Windsor, Ontario to Kissimmee (average of C$ 196). Flying from Windsor, Ontario to Kissimmee in February is currently the most expensive (average of C$ 311). 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.

What is the cheapest time of day to fly from YQG to K1S?

Find hourly flight availability from Windsor to Kissimmee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 1 August 2025.

When flying from Windsor, Ontario to Kissimmee, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 1 August 2025.
Check out reviews from past customers who have flown with Porter Airlines and 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.
Porter Airlines
8.0
Very good
318 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Boarding

8.2

Crew

8.7

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Boarding

8.2

Crew

8.7

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
9,855 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Boarding

8.2

Crew

8.7

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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.

  • 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.

  • What is the cheapest month to book a flight from Windsor, Ontario to Kissimmee?

    Currently, June is the cheapest month in which you can book a flight from Windsor, Ontario to Kissimmee (average of C$ 196). Flying from Windsor, Ontario to Kissimmee in February is currently the most expensive (average of C$ 311). 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.

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 1 August 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 359AverageC$ 630FlexibilityNo 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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