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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 31/10. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — MCO
17 Oct — 24 Oct1
1 adult
1 adult, Economy

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 17 September 2025.

Round-trip from

C$ 502

One-way from

C$ 274

Popular in

June

Cheapest in

April

Average price

C$ 560
Air Canada
  • Air Canada
  • 2/10-5/10
  • 3 total stops
  • 21h 29m total
  • Windsor to Kissimmee
Search Deals
Air Canada
  • Air Canada
  • 31/10
  • 1 total stop
  • 5h 25m total
  • Windsor to Kissimmee
Search Deals
Highest demand for flights based on searches. 21% potential increase in price (C$ 246 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 52 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 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 17 September 2025.

Thu 2/1010:05 a.m.YQG - MCO
2 stops13h 17mAir Canada
Sun 5/107:00 a.m.MCO - YQG
1 stop8h 12mAir Canada
Deal found 17/9C$ 502
Sat 8/119:45 a.m.YQG - MCO
2 stops13h 17mAir Canada
Mon 10/118:30 a.m.MCO - YQG
2 stops10h 44mAir Canada
Deal found 16/9C$ 546
Mon 29/93:55 p.m.YQG - MCO
1 stop7h 53mAir Canada
Fri 3/105:25 p.m.MCO - YQG
2 stops21h 47mAir Canada
Deal found 16/9C$ 692
Mon 29/98:40 a.m.YQG - MCO
1 stop25h 29mMultiple Airlines
Fri 3/108:45 p.m.MCO - YQG
1 stop24h 05mMultiple Airlines
Deal found 16/9C$ 769
Fri 17/108:50 a.m.YQG - MCO
2 stops10h 51mPorter Airlines
Mon 20/101:45 p.m.MCO - YQG
2 stops7h 05mPorter Airlines
Deal found 16/9C$ 891
Mon 17/117:35 a.m.YQG - MCO
2 stops29h 23mPorter Airlines
Thu 20/112:00 p.m.MCO - YQG
2 stops29h 33mPorter Airlines
Deal found 17/9C$ 937

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 17 September 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

Thu 2/10

10:05 a.m.-11:22 p.m.

2 stops13h 17m

Orlando

Sun 5/10

7:00 a.m.-3:12 p.m.

1 stop8h 12m

C$ 502

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Sat 8/11

9:45 a.m.-11:02 p.m.

2 stops13h 17m

Orlando

Mon 10/11

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

2 stops10h 44m

C$ 546

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Mon 29/9

9:55 a.m.-11:22 p.m.

2 stops13h 27m

Orlando

Fri 3/10

5:25 p.m.-3:12 p.m.

2 stops21h 47m

C$ 732

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Mon 29/9

8:40 a.m.-10:09 a.m.

1 stop25h 29m

Orlando

Fri 3/10

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

1 stop24h 05m

C$ 769

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Fri 17/10

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

2 stops10h 51m

Orlando

Mon 20/10

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

2 stops7h 05m

C$ 891

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Mon 17/11

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

2 stops29h 23m

Orlando

Thu 20/11

2:00 p.m.-7:33 p.m.

2 stops29h 33m

C$ 937

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Fri 10/10

4:00 p.m.-11:48 p.m.

1 stop7h 48m

Orlando

Tue 14/10

7:00 a.m.-3:12 p.m.

1 stop8h 12m

C$ 945

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Fri 31/10

9:45 a.m.-3:10 p.m.

1 stop5h 25m

C$ 274

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Fri 3/10

4:00 p.m.-11:48 p.m.

1 stop7h 48m

C$ 308

WindsorOrlando

YQG - MCO

YQGMCO

Windsor

Fri 31/10

7:35 a.m.-6:54 p.m.

2 stops11h 19m

C$ 352

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/9

Showing 1-10 of 11 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

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 17 September 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 17 September 2025.
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
10,000 reviews
Check prices

Crew

7.8

Food

6.3

Boarding

7.3

Comfort

7.1

Entertainment

6.8

Overall

7.1

Reviews

1 / 20
10.0
Excellent

janet,Sep 2025

YOW - YYZ

Really appreciated the leg room despite purchasing an economy ticket. Appreciated the extra complimentary wine. Nice touch. Was given immediate support without asking at check in, at the machine!! Ottawa's boarding was very organized with distinct rows in waiting room. Allowed for the main hall to not be blocked by people waiting to board.
Air Canada
7.1
Good
10,000 reviews
Air Canada
7.1
Good
10,000 reviews
Check prices

Crew

7.8

Food

6.3

Boarding

7.3

Comfort

7.1

Entertainment

6.8

Overall

7.1

Reviews

1 / 20
10.0
Excellent

janet,Sep 2025

YOW - YYZ

Really appreciated the leg room despite purchasing an economy ticket. Appreciated the extra complimentary wine. Nice touch. Was given immediate support without asking at check in, at the machine!! Ottawa's boarding was very organized with distinct rows in waiting room. Allowed for the main hall to not be blocked by people waiting to board.

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$ 502, Air Canada can have you in Kissimmee from Windsor, Ontario in 13h 17m. 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.

  • 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 17 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 356AverageC$ 627FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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.

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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.

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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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