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Kissimmee

$69+ 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MCO
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from New Windsor Stewart to Kissimmee are usually found in January or September, booked 65 days in advance, depart on a Saturday or Tuesday and return on a Monday

Cheap flight deals from Stewart to Kissimmee

Keep the following information in mind while searching for Stewart to Kissimmee flight deals. Data was last updated September 11, 2025.

Round-trip from

$132
(CheapOair)

One-way from

$69
(CheapOair)

Popular in

April

Cheapest in

January

Average price

$170
From New Windsor Stewart to Kissimmee
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One-way flight from New Windsor Stewart to Kissimmee
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Highest demand for flights based on searches. 9% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This CheapOair deal was found by Cheapflights users on 9/9. 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.
Sun 9/2111:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Sun 9/288:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Deal found 9/9$143
This Expedia deal was found by Cheapflights users on 9/11. 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.
Sun 9/2811:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Sun 10/128:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Deal found 9/11$147
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/2611:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Fri 10/317:30 amMCO - SWF
1 stop4h 14mBreeze Airways
Deal found 9/11$154
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Thu 9/1811:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Sun 9/218:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Deal found 9/11$157
This Breeze Airways deal was found by Cheapflights users on 9/11. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Sun 10/128:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Deal found 9/11$160
This Breeze Airways deal was found by Cheapflights users on 9/8. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3011:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Mon 11/37:30 amMCO - SWF
1 stop4h 14mBreeze Airways
Deal found 9/8$161
This CheapOair deal was found by Cheapflights users on 9/9. 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.
Fri 10/3112:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Mon 11/37:30 amMCO - SWF
1 stop4h 14mBreeze Airways
Deal found 9/9$165
This Priceline deal was found by Cheapflights users on 9/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2712:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Fri 10/317:30 amMCO - SWF
1 stop4h 14mBreeze Airways
Deal found 9/9$166
This CheapOair deal was found by Cheapflights users on 9/8. 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 10/3011:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Sun 11/28:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Deal found 9/8$168

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 September 11, 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

Sun 9/21

11:43 am-2:57 pm

Nonstop3h 14m

Orlando

Sun 9/28

8:10 am-11:03 am

Nonstop2h 53m

$143

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sun 9/28

11:43 am-2:57 pm

Nonstop3h 14m

Orlando

Sun 10/12

8:10 am-11:03 am

Nonstop2h 53m

$147

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Fri 10/3

12:24 pm-4:59 pm

1 stop4h 35m

Orlando

Sun 10/12

8:10 am-11:03 am

Nonstop2h 53m

$160

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Thu 10/30

11:43 am-2:57 pm

Nonstop3h 14m

Orlando

Mon 11/3

7:30 am-11:44 am

1 stop4h 14m

$161

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Fri 10/31

12:24 pm-4:59 pm

1 stop4h 35m

Orlando

Mon 11/3

7:30 am-11:44 am

1 stop4h 14m

$163

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 10/27

12:24 pm-4:59 pm

1 stop4h 35m

Orlando

Fri 10/31

7:30 am-11:44 am

1 stop4h 14m

$166

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sun 10/26

11:43 am-2:57 pm

Nonstop3h 14m

Orlando

Sun 11/2

8:10 am-11:03 am

Nonstop2h 53m

$168

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sun 9/21

11:43 am-2:57 pm

Nonstop3h 14m

Orlando

Thu 9/25

8:10 am-11:03 am

Nonstop2h 53m

$168

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 10/6

12:24 pm-4:59 pm

1 stop4h 35m

Orlando

Thu 10/9

8:10 am-11:03 am

Nonstop2h 53m

$180

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Thu 9/18

11:43 am-2:57 pm

Nonstop3h 14m

Orlando

Thu 9/25

8:10 am-11:03 am

Nonstop2h 53m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 19 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 August 29, 2025.

To ensure you get the cheapest price possible for a flight from New Windsor to Kissimmee, you should look to book at least 65 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, May is the cheapest month in which you can book a flight from New Windsor to Kissimmee (average of $206). Flying from New Windsor to Kissimmee in November is currently the most expensive (average of $289). 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 September 11, 2025.

When flying from New Windsor 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 September 11, 2025.
Read through reviews of airlines operating flights from New Windsor to Kissimmee, such as Breeze Airways, JetBlue, and Allegiant Air. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.0
Very good
205 reviews

Overall

8.0

Comfort

8.1

Boarding

8.2

Crew

8.7

Food

6.7

Entertainment

6.5

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.0
Very good
205 reviews
Breeze Airways
8.0
Very good
205 reviews

Overall

8.0

Comfort

8.1

Boarding

8.2

Crew

8.7

Food

6.7

Entertainment

6.5

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
JetBlue
7.2
Good
2,913 reviews
Breeze Airways
8.0
Very good
205 reviews

Overall

8.0

Comfort

8.1

Boarding

8.2

Crew

8.7

Food

6.7

Entertainment

6.5

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Allegiant Air
7.2
Good
702 reviews
Breeze Airways
8.0
Very good
205 reviews

Overall

8.0

Comfort

8.1

Boarding

8.2

Crew

8.7

Food

6.7

Entertainment

6.5

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Spirit Airlines
6.3
Okay
8,023 reviews
Breeze Airways
8.0
Very good
205 reviews

Overall

8.0

Comfort

8.1

Boarding

8.2

Crew

8.7

Food

6.7

Entertainment

6.5

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Frontier
5.8
Fair
3,177 reviews
Breeze Airways
8.0
Very good
205 reviews

Overall

8.0

Comfort

8.1

Boarding

8.2

Crew

8.7

Food

6.7

Entertainment

6.5

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

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 $143, Breeze Airways can have you in Kissimmee from New Windsor in 3h 14m. There are 989 mi between New Windsor and Kissimmee. All flights are typically nonstop.

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

    The cheapest flight price from New Windsor to Kissimmee is $64. On average you can expect to pay $174. The most popular route, (New Windsor Stewart - Orlando), can usually be booked for $132.

  • 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, May is the cheapest month in which you can book a flight from New Windsor to Kissimmee (average of $206). Flying from New Windsor to Kissimmee in November is currently the most expensive (average of $289). 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 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$40Average$103FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$127FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$76Average$137FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$111Average$242FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$121Average$234FlexibilityNo cancel feeOn-timeN/A

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