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$34+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MIA
Jul 27 — Aug 31
Mon 7/27
Mon 8/3
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 June 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/25. 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 8/201:00 pm
SWF
-
FLL
Nonstop3h 12m
Allegiant Air
Thu 9/33:30 pm
FLL
-
SWF
Nonstop3h 10m
Allegiant Air
Deal found 6/25$72
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 8/307:31 pm
SWF
-
FLL
Nonstop3h 12m
Allegiant Air
Thu 9/33:30 pm
FLL
-
SWF
Nonstop3h 10m
Allegiant Air
Deal found 6/24$76
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 8/1310:28 am
SWF
-
FLL
Nonstop3h 09m
Allegiant Air
Sun 8/303:31 pm
FLL
-
SWF
Nonstop3h 10m
Allegiant Air
Deal found 6/27$77
This CheapOair deal was found by Cheapflights users on 6/25. 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 8/231:00 pm
SWF
-
FLL
Nonstop3h 12m
Allegiant Air
Thu 9/33:30 pm
FLL
-
SWF
Nonstop3h 10m
Allegiant Air
Deal found 6/25$83
This Mytrip deal was found by Cheapflights users on 6/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/810:18 am
SWF
-
FLL
Nonstop3h 22m
Allegiant Air
Sun 10/117:55 am
FLL
-
SWF
Nonstop3h 08m
Allegiant Air
Deal found 6/23$86
This CheapOair deal was found by Cheapflights users on 6/25. 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 8/201:00 pm
SWF
-
FLL
Nonstop3h 12m
Allegiant Air
Thu 8/273:31 pm
FLL
-
SWF
Nonstop3h 10m
Allegiant Air
Deal found 6/25$87
This CheapOair deal was found by Cheapflights users on 6/25. 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 7/3010:28 am
SWF
-
FLL
Nonstop3h 09m
Allegiant Air
Sun 8/26:30 am
FLL
-
SWF
Nonstop3h 08m
Allegiant Air
Deal found 6/25$88
This Cheapflightsfares deal was found by Cheapflights users on 6/24. 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.
Sun 10/2511:58 am
SWF
-
FLL
Nonstop3h 22m
Allegiant Air
Sun 11/18:00 am
FLL
-
SWF
Nonstop3h 08m
Allegiant Air
Deal found 6/24$89
This Mytrip deal was found by Cheapflights users on 6/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:28 am
SWF
-
FLL
Nonstop3h 22m
Allegiant Air
Sun 10/47:50 am
FLL
-
SWF
Nonstop3h 08m
Allegiant Air
Deal found 6/23$90
This CheapOair deal was found by Cheapflights users on 6/24. 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 8/231:00 pm
SWF
-
FLL
Nonstop3h 12m
Allegiant Air
Sun 8/303:31 pm
FLL
-
SWF
Nonstop3h 10m
Allegiant Air
Deal found 6/24$92
This Cheapflightsfares deal was found by Cheapflights users on 6/27. 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.
Thu 9/2411:13 am
SWF
-
PIE
Nonstop3h 01m
Allegiant Air
Sun 9/277:35 am
PIE
-
SWF
Nonstop2h 48m
Allegiant Air
Deal found 6/27$109
This Mytrip deal was found by Cheapflights users on 6/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/111:48 am
SWF
-
MCO
Nonstop3h 06m
Breeze Airways
Thu 9/177:20 am
MCO
-
SWF
Nonstop2h 56m
Breeze Airways
Deal found 6/23$121

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 June 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$72
(Kiwi.com)

One-way from

$34
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$250
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. 11% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
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 June 27, 2026.
Use the filters below to find and compare flights from New Windsor to Florida that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorTampa

SWF - PIE

SWFPIE

New Windsor Stewart

Thu 9/24

11:13 am-2:14 pm

Nonstop3h 01m

Tampa St. Petersburg

Sun 9/27

7:35 am-10:23 am

Nonstop2h 48m

$109

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Thu 8/20

1:00 pm-4:12 pm

Nonstop3h 12m

Fort Lauderdale

Sun 8/23

9:00 am-12:10 pm

Nonstop3h 10m

$128

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Tue 8/25

11:48 am-2:54 pm

Nonstop3h 06m

Orlando

Tue 9/1

8:10 am-11:08 am

Nonstop2h 58m

$133
Quickest round-trip

New WindsorTampa

SWF - PIE

SWFPIE

New Windsor Stewart

Thu 10/1

7:36 pm-10:36 pm

Nonstop3h 00m

Tampa St. Petersburg

Sun 10/4

3:31 pm-6:19 pm

Nonstop2h 48m

$163

New WindsorTampa

SWF - PIE

SWFPIE

New Windsor Stewart

Thu 10/1

7:36 pm-10:36 pm

Nonstop3h 00m

Tampa St. Petersburg

Thu 10/8

2:37 pm-5:25 pm

Nonstop2h 48m

$164

New WindsorTampa

SWF - PIE

SWFPIE

New Windsor Stewart

Tue 7/14

6:19 pm-9:16 pm

Nonstop2h 57m

Tampa St. Petersburg

Tue 7/21

2:37 pm-5:29 pm

Nonstop2h 52m

$166

New WindsorFort Myers

SWF - RSW

SWFRSW

New Windsor Stewart

Fri 9/4

12:17 pm-5:33 pm

1 stop5h 16m

Fort Myers SW Florida Intl

Mon 9/7

7:10 am-11:37 am

1 stop4h 27m

$169

New WindsorTampa

SWF - PIE

SWFPIE

New Windsor Stewart

Sun 11/15

5:37 pm-8:46 pm

Nonstop3h 09m

Tampa St. Petersburg

Thu 11/19

7:00 am-9:54 am

Nonstop2h 54m

$170

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Wed 8/5

12:05 pm-11:44 pm

1 stop11h 39m

Orlando

Wed 8/12

7:00 am-11:25 am

1 stop4h 25m

$173

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Thu 8/6

10:33 am-1:39 pm

Nonstop3h 06m

Orlando

Thu 8/13

6:55 am-9:53 am

Nonstop2h 58m

$178

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/26

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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, September is the cheapest month in which you can book a flight from New Windsor to Florida (average of $43). Flying from New Windsor to Florida in December is currently the most expensive (average of $88). 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 June 27, 2026.

It’s typically best to fly out from New Windsor to Florida in the evening. Doing so could potentially save you 52% on the flight price compared to flying at noon, which is usually more expensive.

How much does it cost to fly round-trip from New Windsor to Florida?

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

Booking 87 days in advance of your planned departure date is, on average, the best time to get cheap flights from New Windsor to Florida. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 June 27, 2026.

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. Wednesday mornings 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 June 27, 2026.
Peruse reviews from past customers who have flown with Breeze Airways,Allegiant Air, andJetBlue 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
293 reviews

Boarding

8.4

Comfort

8.2

Entertainment

6.7

Overall

8.2

Crew

8.8

Food

6.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Breeze Airways
8.2
Very good
293 reviews
Breeze Airways
8.2
Very good
293 reviews

Boarding

8.4

Comfort

8.2

Entertainment

6.7

Overall

8.2

Crew

8.8

Food

6.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Allegiant Air
7.3
Good
693 reviews
Breeze Airways
8.2
Very good
293 reviews

Boarding

8.4

Comfort

8.2

Entertainment

6.7

Overall

8.2

Crew

8.8

Food

6.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
JetBlue
7.1
Good
3,014 reviews
Breeze Airways
8.2
Very good
293 reviews

Boarding

8.4

Comfort

8.2

Entertainment

6.7

Overall

8.2

Crew

8.8

Food

6.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.

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?

    Allegiant Air and Breeze Airways can get you from New Windsor to Florida in just under 3h 06m. Your travel time will be generally consistent. Airlines will cover a distance of 989 mi. Most flights are nonstop.

  • 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.

  • 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, September is the cheapest month in which you can book a flight from New Windsor to Florida (average of $43). Flying from New Windsor to Florida in December is currently the most expensive (average of $88). 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 4 airlines flying from Stewart to Florida

Discover the top 4 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 June 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$43Average$148FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$49Average$192FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$108Average$271FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$128Average$232FlexibilityNo cancel feeOn-timeN/A

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