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Florida Keys

$93+ Cheap flights from New Windsor (SWF) to Florida Keys

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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — EYW
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap flight deals from Stewart to Florida Keys

Cheapest flights from Stewart to Florida Keys
Explore the most affordable flight options available from Stewart to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/13. 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 12/1811:09 amSWF - EYW
1 stop22h 08mMultiple Airlines
Mon 12/221:10 pmEYW - SWF
1 stop21h 53mMultiple Airlines
Deal found 12/13$345
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Sat 12/209:45 amSWF - EYW
1 stop22h 30mMultiple Airlines
Mon 12/221:10 pmEYW - SWF
1 stop21h 53mMultiple Airlines
Deal found 12/15$355
This Kiwi.com deal was found by Cheapflights users on 12/13. 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 12/1411:43 amSWF - EYW
1 stop20h 32mBreeze Airways
Sun 12/218:55 amEYW - SWF
2 stops26h 49mBreeze Airways
Deal found 12/13$377
This Kiwi.com deal was found by Cheapflights users on 12/13. 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 12/1411:43 amSWF - EYW
1 stop20h 32mMultiple Airlines
Sun 12/213:24 pmEYW - SWF
1 stop26h 56mMultiple Airlines
Deal found 12/13$384
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Sat 12/209:45 amSWF - EYW
1 stop28h 49mAllegiant Air
Tue 12/233:15 pmEYW - SWF
1 stop25h 29mAllegiant Air
Deal found 12/15$419
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Sat 12/209:45 amSWF - EYW
1 stop22h 30mMultiple Airlines
Fri 12/269:57 amEYW - SWF
1 stop9h 31mMultiple Airlines
Deal found 12/14$424
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Fri 12/1912:24 pmSWF - EYW
2 stops18h 43mBreeze Airways
Mon 12/221:10 pmEYW - SWF
1 stop21h 53mBreeze Airways
Deal found 12/15$442
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/1512:24 pmSWF - EYW
2 stops22h 41mBreeze Airways
Mon 12/221:10 pmEYW - SWF
1 stop21h 53mBreeze Airways
Deal found 12/14$451
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 - EYW
2 stops13h 54mMultiple Airlines
Mon 12/291:10 pmEYW - SWF
1 stop21h 53mMultiple Airlines
Deal found 12/14$469
This Kiwi.com deal was found by Cheapflights users on 12/13. 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 12/1811:09 amSWF - EYW
1 stop10h 33mAllegiant Air
Sun 12/213:24 pmEYW - SWF
1 stop26h 56mAllegiant Air
Deal found 12/13$471
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/227:10 pmSWF - EYW
1 stop19h 15mMultiple Airlines
Fri 12/269:57 amEYW - SWF
1 stop9h 31mMultiple Airlines
Deal found 12/14$472

Find flight deals from Stewart to Florida Keys

Keep the following information in mind while searching for Stewart to Florida Keys flight deals. Data was last updated December 15, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$257
(Kiwi.com)

One-way from

$93
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$308
Provider with most accurate pricing for New York (NYC)-Miami flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Miami flights.
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From New Windsor Stewart to Florida Keys
Search Deals
One-way flight from New Windsor Stewart to Florida Keys
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Florida Keys 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 15, 2025.
Use the filters below to find and compare flights from New Windsor to Florida Keys that are best for you.

Fly from

Stewart

Fly to

Florida Keys

Route

Depart

Return

Price

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 1/29

10:48 am-9:37 pm

1 stop10h 49m

Key West

Sun 2/1

12:51 pm-10:19 am

1 stop21h 28m

$265

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 1/11

10:48 am-9:37 pm

1 stop10h 49m

Key West

Wed 1/14

4:06 pm-9:58 am

1 stop17h 52m

$267

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 1/11

10:48 am-9:37 pm

1 stop10h 49m

Key West

Sun 1/18

12:51 pm-10:19 am

1 stop21h 28m

$275

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 1/29

10:48 am-9:37 pm

1 stop10h 49m

Key West

Thu 2/5

9:46 am-11:31 am

2 stops25h 45m

$276

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 1/22

10:48 am-9:37 pm

1 stop10h 49m

Key West

Sun 1/25

3:46 pm-6:43 pm

1 stop26h 57m

$305

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 2/5

10:48 am-9:37 pm

1 stop10h 49m

Key West

Sun 2/8

3:46 pm-6:43 pm

1 stop26h 57m

$313

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 2/5

10:48 am-9:37 pm

1 stop10h 49m

Key West

Sun 2/8

9:46 am-11:31 am

2 stops25h 45m

$329

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 3/5

11:48 am-12:26 pm

1 stop24h 38m

Key West

Sun 3/8

4:14 pm-10:12 am

1 stop17h 58m

$333

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 12/18

11:09 am-9:17 am

1 stop22h 08m

Key West

Mon 12/22

1:10 pm-11:03 am

1 stop21h 53m

$345

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 1/22

12:13 pm-12:26 pm

1 stop24h 13m

$93

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 25 results
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Best time to book a flight from Stewart to Florida Keys

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

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

Currently, May is the cheapest month in which you can book a flight from New Windsor to Florida Keys (average of $151). Flying from New Windsor to Florida Keys in August is currently the most expensive (average of $306). 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.

Related info for your journey

Find useful and relevant information for your journey from Stewart to Florida Keys. 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 Keys?

    If you book a flight to Florida Keys 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.

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

    Allegiant Air can get you from New Windsor to Florida Keys in just under 10h 49m. Your travel time can differ by up to . There are 1250 mi between New Windsor and Florida Keys.

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

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

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

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

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

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

    Currently, May is the cheapest month in which you can book a flight from New Windsor to Florida Keys (average of $151). Flying from New Windsor to Florida Keys in August is currently the most expensive (average of $306). 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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