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Kissimmee

$55+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MCO
Mar 10 — Mar 171
Tue 3/10
Tue 3/17
1 adult, Economy
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Cheapflights Tip: The best prices from New Windsor Stewart to Kissimmee are usually found in September or November, booked 38 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 February 8, 2026.

This Mytrip deal was found by Cheapflights users on 2/7. 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.
Mon 3/2312:11 pm
SWF
-
MCO
1 stop4h 38m
Breeze Airways
Fri 3/277:15 am
MCO
-
SWF
1 stop4h 16m
Breeze Airways
Deal found 2/7$120
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 8/309:38 am
SWF
-
MCO
Nonstop3h 06m
Breeze Airways
Fri 9/47:15 am
MCO
-
SWF
1 stop4h 20m
Breeze Airways
Deal found 2/5$121
This Mytrip deal was found by Cheapflights users on 2/6. 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.
Mon 3/2312:11 pm
SWF
-
MCO
1 stop4h 38m
Breeze Airways
Mon 3/307:15 am
MCO
-
SWF
1 stop4h 16m
Breeze Airways
Deal found 2/6$129
This Mytrip deal was found by Cheapflights users on 2/5. 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.
Mon 3/212:11 pm
SWF
-
MCO
1 stop4h 38m
Breeze Airways
Fri 3/67:15 am
MCO
-
SWF
1 stop4h 16m
Breeze Airways
Deal found 2/5$131
This Mytrip deal was found by Cheapflights users on 2/7. 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.
Mon 2/2312:11 pm
SWF
-
MCO
1 stop4h 38m
Breeze Airways
Fri 2/277:15 am
MCO
-
SWF
1 stop4h 16m
Breeze Airways
Deal found 2/7$133
This Mytrip deal was found by Cheapflights users on 2/7. 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.
Mon 3/2312:11 pm
SWF
-
MCO
1 stop4h 38m
Breeze Airways
Thu 3/268:10 am
MCO
-
SWF
Nonstop2h 58m
Breeze Airways
Deal found 2/7$134
This Mytrip deal was found by Cheapflights users on 2/7. 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.
Mon 3/212:11 pm
SWF
-
MCO
1 stop4h 38m
Breeze Airways
Thu 3/58:10 am
MCO
-
SWF
Nonstop2h 58m
Breeze Airways
Deal found 2/7$138
This CheapOair deal was found by Cheapflights users on 2/6. 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.
Mon 2/2312:11 pm
SWF
-
MCO
1 stop4h 38m
Breeze Airways
Fri 3/67:15 am
MCO
-
SWF
1 stop4h 16m
Breeze Airways
Deal found 2/6$139
This Booking.com deal was found by Cheapflights users on 2/5. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/912:11 pm
SWF
-
MCO
1 stop4h 38m
Breeze Airways
Thu 3/128:10 am
MCO
-
SWF
Nonstop2h 58m
Breeze Airways
Deal found 2/5$140
This Expedia deal was found by Cheapflights users on 2/5. 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.
Sat 8/2912:05 pm
SWF
-
MCO
1 stop4h 57m
Breeze Airways
Wed 9/97:00 am
MCO
-
SWF
1 stop4h 25m
Breeze Airways
Deal found 2/5$142

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 February 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$120
(Mytrip)

One-way from

$55
(Mytrip)

Popular in

April

Cheapest in

September

Average price

$235
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. 11% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 8, 2026.
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 3/23

12:11 pm-4:49 pm

1 stop4h 38m

Orlando

Thu 3/26

8:10 am-11:08 am

Nonstop2h 58m

$134

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 3/23

12:11 pm-4:49 pm

1 stop4h 38m

Orlando

Mon 3/30

7:15 am-11:31 am

1 stop4h 16m

$134

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 3/2

12:11 pm-4:49 pm

1 stop4h 38m

Orlando

Thu 3/5

8:10 am-11:08 am

Nonstop2h 58m

$138

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Fri 3/6

12:11 pm-4:49 pm

1 stop4h 38m

Orlando

Thu 3/12

8:10 am-11:08 am

Nonstop2h 58m

$155

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sun 5/24

9:38 am-12:44 pm

Nonstop3h 06m

Orlando

Sat 5/30

7:00 am-11:25 am

1 stop4h 25m

$156

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sun 5/3

11:48 am-3:07 pm

Nonstop3h 19m

Orlando

Sat 5/30

7:00 am-11:25 am

1 stop4h 25m

$156

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 5/18

12:15 pm-4:49 pm

1 stop4h 34m

Orlando

Thu 5/21

6:00 am-8:58 am

Nonstop2h 58m

$161

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sun 6/21

9:38 am-12:44 pm

Nonstop3h 06m

Orlando

Sun 6/28

6:00 am-8:58 am

Nonstop2h 58m

$162

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sun 5/17

9:38 am-12:44 pm

Nonstop3h 06m

Orlando

Thu 5/21

6:00 am-8:58 am

Nonstop2h 58m

$163

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sun 3/22

11:48 am-3:07 pm

Nonstop3h 19m

Orlando

Sun 3/29

8:10 am-11:08 am

Nonstop2h 58m

$166

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

Showing 1-10 of 21 results
1
2
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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 January 30, 2026.

To ensure you get the cheapest price possible for a flight from New Windsor to Kissimmee, you should look to book at least 37 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, March is the cheapest month in which you can book a flight from New Windsor to Kissimmee (average of $38). 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 February 8, 2026.

It’s optimal to fly from New Windsor to Kissimmee in the morning. By choosing this option you can save up to 58% 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 February 8, 2026.
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
8.1
Very good
267 reviews

Boarding

8.3

Food

6.7

Crew

8.7

Comfort

8.2

Entertainment

6.6

Overall

8.1

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Breeze Airways
8.1
Very good
267 reviews
Breeze Airways
8.1
Very good
267 reviews

Boarding

8.3

Food

6.7

Crew

8.7

Comfort

8.2

Entertainment

6.6

Overall

8.1

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
JetBlue
7.2
Good
2,896 reviews
Breeze Airways
8.1
Very good
267 reviews

Boarding

8.3

Food

6.7

Crew

8.7

Comfort

8.2

Entertainment

6.6

Overall

8.1

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Spirit Airlines
6.3
Okay
8,429 reviews
Breeze Airways
8.1
Very good
267 reviews

Boarding

8.3

Food

6.7

Crew

8.7

Comfort

8.2

Entertainment

6.6

Overall

8.1

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Frontier
5.7
Fair
3,051 reviews
Breeze Airways
8.1
Very good
267 reviews

Boarding

8.3

Food

6.7

Crew

8.7

Comfort

8.2

Entertainment

6.6

Overall

8.1

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

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 $134, 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 $54. On average you can expect to pay $168. The most popular route, (New Windsor Stewart - Orlando), can usually be booked for $142.

  • 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, March is the cheapest month in which you can book a flight from New Windsor to Kissimmee (average of $38). 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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Alternative routes for Stewart to Kissimmee

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 February 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$40Average$101FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$55Average$218FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$80Average$164FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$111Average$233FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$125Average$235FlexibilityNo cancel feeOn-timeN/A

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