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Kissimmee

$53+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MCO
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
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 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 julio 30, 2025.

Round-trip from

$118
(Priceline)

One-way from

$53
(Breeze Airways)

Popular in

April

Cheapest in

September

Average price

$215
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 ($24 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 July 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 julio 30, 2025.

This Priceline deal was found by Cheapflights users on 7/29. 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.
mar. 9/212:36 pmSWF - MCO
Nonstop3h 04mBreeze Airways
vie. 9/57:30 amMCO - SWF
1 stop4h 14mBreeze Airways
Deal found 7/29$118
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/225:36 pmSWF - MCO
1 stop14h 28mMultiple Airlines
lun. 8/256:20 amMCO - SWF
1 stop10h 26mMultiple Airlines
Deal found 7/28$177

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 julio 30, 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

mar. 9/2

12:36 pm-3:40 pm

Nonstop3h 04m

Orlando

vie. 9/5

7:30 am-11:44 am

1 stop4h 14m

$118

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

vie. 8/22

5:36 pm-8:04 am

1 stop14h 28m

Orlando

lun. 8/25

6:20 am-4:46 pm

1 stop10h 26m

$177

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

vie. 9/5

12:24 pm-4:59 pm

1 stop4h 35m

$53

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

lun. 8/18

7:37 pm-8:04 am

1 stop12h 27m

$83

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 July 25, 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, 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 $288). 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 julio 30, 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 julio 30, 2025.
Read through reviews of airlines operating flights from New Windsor to Kissimmee, such as Breeze Airways. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.0
Very good
191 reviews

Entertainment

6.5

Boarding

8.2

Overall

8.0

Food

6.7

Comfort

8.1

Crew

8.7

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
191 reviews
Breeze Airways
8.0
Very good
191 reviews

Entertainment

6.5

Boarding

8.2

Overall

8.0

Food

6.7

Comfort

8.1

Crew

8.7

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.

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

    The cheapest flight price from New Windsor to Kissimmee is $91. On average you can expect to pay $173. The most popular route, (New Windsor Stewart - Orlando), can usually be booked for $123.

  • 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 $288). 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.

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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 julio 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$40Average$101FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$127FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$76Average$154FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$111Average$242FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$121Average$236FlexibilityNo cancel feeOn-timeN/A

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