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$46+ Cheap flights from New Windsor (SWF) to Florida

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 — MIA
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from Stewart to Florida

Cheapest flights from Stewart to Florida
Explore the most affordable flight options available from Stewart to Florida. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/21. 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 12/2511:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Tue 12/308:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Deal found 12/21$345
This Booking.com deal was found by Cheapflights users on 12/21. 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.
Tue 12/3011:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Thu 1/18:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Deal found 12/21$349
This Cheapflightsfares deal was found by Cheapflights users on 12/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/228:25 pmSWF - FLL
Nonstop3h 13mAllegiant Air
Fri 12/268:00 amFLL - SWF
Nonstop3h 07mAllegiant Air
Deal found 12/21$357
This Booking.com deal was found by Cheapflights users on 12/20. 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.
Thu 12/2511:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Mon 12/297:30 amMCO - SWF
1 stop4h 14mBreeze Airways
Deal found 12/20$362
This Gotogate deal was found by Cheapflights users on 12/22. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/234:50 pmSWF - PIE
Nonstop3h 00mAllegiant Air
Fri 12/264:39 pmPIE - SWF
Nonstop2h 49mAllegiant Air
Deal found 12/22$372
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 12/228:25 pmSWF - FLL
Nonstop3h 13mAllegiant Air
Mon 12/297:40 amFLL - SWF
Nonstop3h 07mAllegiant Air
Deal found 12/20$372
This CheapOair deal was found by Cheapflights users on 12/21. 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
Mon 1/57:30 amMCO - SWF
1 stop4h 14mBreeze Airways
Deal found 12/21$374
This CheapOair deal was found by Cheapflights users on 12/21. 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 1/18:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Deal found 12/21$377
This Booking.com deal was found by Cheapflights users on 12/21. 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.
Thu 12/2511:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Fri 12/267:30 amMCO - SWF
1 stop4h 14mBreeze Airways
Deal found 12/21$384
This Kiwi.com deal was found by Cheapflights users on 12/23. 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 12/234:50 pmSWF - PIE
Nonstop3h 00mAllegiant Air
Sun 12/287:10 amPIE - SWF
Nonstop2h 49mAllegiant Air
Deal found 12/23$391
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Wed 12/315:34 pmSWF - EYW
1 stop14h 41mMultiple Airlines
Sun 1/48:55 amEYW - SWF
2 stops26h 49mMultiple Airlines
Deal found 12/21$408
This Trip.com deal was found by Cheapflights users on 12/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/234:50 pmSWF - PIE
Nonstop3h 00mAllegiant Air
Thu 1/297:10 amPIE - SWF
Nonstop2h 48mAllegiant Air
Deal found 12/22$409

Find flight deals from Stewart to Florida

Keep the following information in mind while searching for Stewart to Florida flight deals. Data was last updated December 23, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$89
(Booking.com)

One-way from

$46
(Booking.com)

Popular in

April

Cheapest in

September

Average price

$272
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 Florida
Search Deals
One-way flight from New Windsor Stewart to Florida
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($8 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 Florida 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 23, 2025.
Use the filters below to find and compare flights from New Windsor to Florida that are best for you.

Fly from

Stewart

Fly to

Florida

Route

Depart

Return

Price

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 2/2

12:11 pm-4:49 pm

1 stop4h 38m

Orlando

Fri 2/6

7:15 am-11:31 am

1 stop4h 16m

$89

New WindsorPunta Gorda

SWF - PGD

SWFPGD

New Windsor Stewart

Mon 3/2

7:33 pm-10:47 pm

Nonstop3h 14m

Punta Gorda

Fri 3/6

3:53 pm-6:46 pm

Nonstop2h 53m

$96

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Mon 2/2

11:09 am-2:52 pm

Nonstop3h 43m

Fort Lauderdale

Fri 2/6

7:15 am-10:19 am

Nonstop3h 04m

$96

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Fri 1/30

11:09 am-2:52 pm

Nonstop3h 43m

Fort Lauderdale

Mon 2/2

7:15 am-10:19 am

Nonstop3h 04m

$96

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Mon 2/9

11:09 am-2:52 pm

Nonstop3h 43m

Fort Lauderdale

Thu 2/12

7:50 am-10:52 am

Nonstop3h 02m

$96

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Fri 2/6

11:09 am-2:52 pm

Nonstop3h 43m

Fort Lauderdale

Thu 2/12

7:50 am-10:52 am

Nonstop3h 02m

$96

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Mon 1/5

11:37 am-2:50 pm

Nonstop3h 13m

Fort Lauderdale

Fri 1/9

7:15 am-10:19 am

Nonstop3h 04m

$98

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Mon 1/19

11:09 am-2:52 pm

Nonstop3h 43m

Fort Lauderdale

Mon 1/26

7:15 am-10:19 am

Nonstop3h 04m

$100

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Fri 1/23

11:09 am-2:52 pm

Nonstop3h 43m

Fort Lauderdale

Fri 1/30

7:15 am-10:19 am

Nonstop3h 04m

$100

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

$108

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 60 results
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Best time to book a flight from Stewart to Florida

Have a flexible travel schedule? Discover the best time to fly to Florida 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 Florida

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

Currently, January is the cheapest month in which you can book a flight from New Windsor to Florida (average of $29). Flying from New Windsor to Florida 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 FL?

Find hourly flight availability from Stewart to Florida. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 23, 2025.

It’s typically best to fly out from New Windsor to Florida in the afternoon. Doing so could potentially save you 29% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from New Windsor to Florida?

Use this chart to determine the cheapest time to fly round-trip from Stewart to Florida. Price data was last updated on December 20, 2025.

Travelers seeking maximum savings on their New Windsor to Florida flight should consider departing on Friday mornings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Florida

Get insights into the airlines that provide service to Florida. 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 Florida. Reviews last updated December 23, 2025.
Peruse reviews from past customers who have flown with Breeze Airways, JetBlue, and Allegiant Air from New Windsor to Florida 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.
Breeze Airways
8.2
Very good
249 reviews

Overall

8.2

Boarding

8.4

Comfort

8.2

Crew

8.8

Entertainment

6.7

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
249 reviews
Breeze Airways
8.2
Very good
249 reviews

Overall

8.2

Boarding

8.4

Comfort

8.2

Crew

8.8

Entertainment

6.7

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
2,898 reviews
Breeze Airways
8.2
Very good
249 reviews

Overall

8.2

Boarding

8.4

Comfort

8.2

Crew

8.8

Entertainment

6.7

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.
Allegiant Air
7.2
Good
701 reviews
Breeze Airways
8.2
Very good
249 reviews

Overall

8.2

Boarding

8.4

Comfort

8.2

Crew

8.8

Entertainment

6.7

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
8,196 reviews
Breeze Airways
8.2
Very good
249 reviews

Overall

8.2

Boarding

8.4

Comfort

8.2

Crew

8.8

Entertainment

6.7

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
3,075 reviews
Breeze Airways
8.2
Very good
249 reviews

Overall

8.2

Boarding

8.4

Comfort

8.2

Crew

8.8

Entertainment

6.7

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 Florida. 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 Florida?

    New Windsor Stewart (SWF) is the airport you will fly out of if you book a flight from New Windsor to Florida. It is only a 4.3 mi journey to Stewart (SWF) from New Windsor’s city center.

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

    Breeze Airways and Allegiant Air can get you from New Windsor to Florida in just under 3h 14m. Your travel time can differ by up to 1h 24m. Airlines will cover a distance of 1102 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from New Windsor to Florida?

    The most popular route from New Windsor to Florida is New Windsor Stewart - Fort Lauderdale. You may also consider New Windsor Stewart - Orlando or New Windsor Stewart - Tampa St. Petersburg.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Stewart to Florida 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 Florida?

    Currently, January is the cheapest month in which you can book a flight from New Windsor to Florida (average of $29). Flying from New Windsor to Florida 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 Florida

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 Florida

Discover the top 5 airlines that operate flights from Stewart to Florida. 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 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$40Average$93FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$59Average$153FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$76Average$160FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$88Average$215FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$111Average$274FlexibilityNo cancel feeOn-time62%

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