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Kissimmee

$38+ Cheap flights from New Windsor (SWF) to Kissimmee, FL

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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MCO
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheapflights Tip: The best prices from New Windsor Stewart to Kissimmee are usually found in September or January, booked 40 days in advance, depart on a Tuesday or Saturday and return on a Monday

Cheap flight deals from Stewart to Kissimmee

Cheapest flights from Stewart to Kissimmee
Explore the most affordable flight options available from Stewart to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This CheapOair deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Fri 1/307:15 amMCO - SWF
1 stop4h 16mBreeze Airways
Deal found 12/17$289
This CheapOair deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Sun 1/118:35 amMCO - SWF
Nonstop2h 58mBreeze Airways
Deal found 12/16$301
This Kiwi.com deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2212:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Sun 1/118:35 amMCO - SWF
Nonstop2h 58mBreeze Airways
Deal found 12/16$311
This CheapOair deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Sun 1/188:35 amMCO - SWF
Nonstop2h 58mBreeze Airways
Deal found 12/17$326
This CheapOair deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Thu 1/158:35 amMCO - SWF
Nonstop2h 58mBreeze Airways
Deal found 12/17$328
This Expedia deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Fri 1/97:15 amMCO - SWF
1 stop4h 16mBreeze Airways
Deal found 12/17$341
This Kiwi.com deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2212:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Thu 12/258:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Deal found 12/16$342
This Kiwi.com deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2111:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Thu 1/88:35 amMCO - SWF
Nonstop2h 58mBreeze Airways
Deal found 12/15$348
This Kiwi.com deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Mon 1/57:30 amMCO - SWF
1 stop4h 14mBreeze Airways
Deal found 12/17$349
This CheapOair deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Thu 1/228:35 amMCO - SWF
Nonstop2h 58mBreeze Airways
Deal found 12/15$350
This Kiwi.com deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2212:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Tue 12/238:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Deal found 12/15$352

Find flight deals from Stewart to Kissimmee

Keep the following information in mind while searching for Stewart to Kissimmee flight deals. Data was last updated December 18, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$99
(Expedia)

One-way from

$38
(CheapOair)

Popular in

December

Cheapest in

September

Average price

$338
Provider with most accurate pricing for New York (NYC)-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Orlando (ORL) flights.
Search Deals
From New Windsor Stewart to Kissimmee
Search Deals
One-way flight from New Windsor Stewart to Kissimmee
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($7 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart 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 2,558,603 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from New Windsor to Kissimmee that are best for you.

Fly from

Stewart

Fly to

Kissimmee

Route

Depart

Return

Price

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 1/26

12:11 pm-4:49 pm

1 stop4h 38m

Orlando

Fri 1/30

7:15 am-11:31 am

1 stop4h 16m

$104

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 2/2

12:11 pm-4:49 pm

1 stop4h 38m

Orlando

Thu 2/5

8:10 am-11:08 am

Nonstop2h 58m

$107

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Fri 2/6

12:11 pm-4:49 pm

1 stop4h 38m

Orlando

Sun 2/8

8:10 am-11:08 am

Nonstop2h 58m

$131

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sun 2/8

11:48 am-3:07 pm

Nonstop3h 19m

Orlando

Fri 2/13

7:15 am-11:31 am

1 stop4h 16m

$139

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sun 1/18

12:13 pm-3:32 pm

Nonstop3h 19m

Orlando

Thu 1/22

8:35 am-11:33 am

Nonstop2h 58m

$142

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 1/19

12:11 pm-4:49 pm

1 stop4h 38m

Orlando

Thu 1/22

8:35 am-11:33 am

Nonstop2h 58m

$144

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Thu 2/5

11:48 am-3:07 pm

Nonstop3h 19m

Orlando

Sun 2/8

8:10 am-11:08 am

Nonstop2h 58m

$148

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Fri 2/6

12:11 pm-4:49 pm

1 stop4h 38m

Orlando

Sun 2/15

8:10 am-11:08 am

Nonstop2h 58m

$152

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sun 1/25

12:13 pm-3:32 pm

Nonstop3h 19m

Orlando

Sun 2/1

8:35 am-11:33 am

Nonstop2h 58m

$158

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 2/2

12:11 pm-4:49 pm

1 stop4h 38m

$50

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 17 results
1
2

Best time to book a flight from Stewart to Kissimmee

Have a flexible travel schedule? Discover the best time to fly to Kissimmee from Stewart 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 New Windsor to Kissimmee

How far ahead should I book a flight from New Windsor to Kissimmee?

Use this chart to determine the optimal time to book a round-trip flight from Stewart to Kissimmee. Price data was last updated on December 12, 2025.

To ensure you get the cheapest price possible for a flight from New Windsor to Kissimmee, you should look to book at least 40 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, January is the cheapest month in which you can book a flight from New Windsor to Kissimmee (average of $29). Flying from New Windsor to Kissimmee in July is currently the most expensive (average of $78). 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 SWF to K1S?

Find hourly flight availability from Stewart 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 December 18, 2025.

It’s optimal to fly from New Windsor to Kissimmee in the evening. By choosing this option you can save up to 43% on the cost of your flight, compared to a flight at noon.

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 December 18, 2025.
Read through reviews of airlines operating flights from New Windsor to Kissimmee, such as Breeze Airways, JetBlue, and Spirit Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.2
Very good
248 reviews

Boarding

8.4

Entertainment

6.7

Crew

8.8

Overall

8.2

Comfort

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Breeze Airways
8.2
Very good
248 reviews
Breeze Airways
8.2
Very good
248 reviews

Boarding

8.4

Entertainment

6.7

Crew

8.8

Overall

8.2

Comfort

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
JetBlue
7.2
Good
2,895 reviews
Breeze Airways
8.2
Very good
248 reviews

Boarding

8.4

Entertainment

6.7

Crew

8.8

Overall

8.2

Comfort

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Spirit Airlines
6.3
Okay
8,188 reviews
Breeze Airways
8.2
Very good
248 reviews

Boarding

8.4

Entertainment

6.7

Crew

8.8

Overall

8.2

Comfort

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Frontier
5.8
Fair
3,080 reviews
Breeze Airways
8.2
Very good
248 reviews

Boarding

8.4

Entertainment

6.7

Crew

8.8

Overall

8.2

Comfort

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.

Related info for your journey

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

    If you book a flight to Kissimmee from New Windsor, you will be flying from Stewart, which is the city’s only airport. New Windsor Stewart (SWF) is located 4.3 mi from the center of New Windsor. There are 0 flights from Stewart to Kissimmee per day from 5 different airlines.

  • How long is the flight from New Windsor to Kissimmee?

    For as low as $104, Breeze Airways can have you in Kissimmee from New Windsor in 4h 38m. There are 989 mi between New Windsor and Kissimmee.

  • What are the cheapest flights from New Windsor to Kissimmee?

    The cheapest flight price from New Windsor to Kissimmee is $59. On average you can expect to pay $177. The most popular route, (New Windsor Stewart - Orlando), can usually be booked for $129.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Stewart 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 New Windsor to Kissimmee?

    Currently, January is the cheapest month in which you can book a flight from New Windsor to Kissimmee (average of $29). Flying from New Windsor to Kissimmee in July is currently the most expensive (average of $78). 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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See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Stewart to Kissimmee

Discover the top 5 airlines that operate flights from Stewart 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 2,558,603 searches. Data last updated December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$40Average$93FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$142FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$76Average$154FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$111Average$233FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$120Average$233FlexibilityNo cancel feeOn-timeN/A

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