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Florida Keys

$109+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — EYW
nov. 28 — dic. 51
vie. 11/28
vie. 12/5
1 adult, Economy
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Find 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 octubre 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/2111:12 amSWF - EYW
1 stop26h 17mMultiple Airlines
lun. 11/248:55 amEYW - SWF
1 stop23h 58mMultiple Airlines
Deal found 10/28$230
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/711:43 amSWF - EYW
1 stop20h 32mMultiple Airlines
dom. 12/1412:20 pmEYW - SWF
1 stop23h 17mMultiple Airlines
Deal found 10/28$252
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/2711:43 amSWF - EYW
1 stop20h 32mMultiple Airlines
jue. 12/44:34 pmEYW - SWF
1 stop26h 06mMultiple Airlines
Deal found 10/28$256
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/2711:43 amSWF - EYW
1 stop20h 32mBreeze Airways
jue. 12/48:55 amEYW - SWF
2 stops26h 49mBreeze Airways
Deal found 10/28$265
This Mytrip deal was found by Cheapflights users on 10/28. 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. 11/1411:01 amSWF - MIA
2 stops22h 57mMultiple Airlines
dom. 11/236:46 amMIA - SWF
2 stops27h 21mMultiple Airlines
Deal found 10/28$269
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/1111:16 amSWF - EYW
1 stop21h 55mAllegiant Air
lun. 11/174:47 pmEYW - SWF
1 stop17h 39mAllegiant Air
Deal found 10/29$287
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
vie. 10/3112:24 pmSWF - EYW
2 stops21h 43mMultiple Airlines
lun. 11/39:11 pmEYW - SWF
1 stop13h 15mMultiple Airlines
Deal found 10/26$293
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
jue. 12/1111:09 amSWF - EYW
1 stop10h 28mAllegiant Air
sáb. 12/135:46 pmEYW - SWF
1 stop16h 33mAllegiant Air
Deal found 10/26$302
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/1611:43 amSWF - EYW
1 stop20h 32mBreeze Airways
jue. 11/208:55 amEYW - SWF
2 stops26h 49mBreeze Airways
Deal found 10/28$308
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/136:14 pmSWF - EYW
1 stop13h 57mMultiple Airlines
dom. 11/1612:15 pmEYW - SWF
1 stop22h 56mMultiple Airlines
Deal found 10/28$314
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
jue. 12/1111:43 amSWF - EYW
1 stop20h 32mMultiple Airlines
sáb. 12/135:46 pmEYW - SWF
1 stop16h 33mMultiple Airlines
Deal found 10/27$318
This Mytrip deal was found by Cheapflights users on 10/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/312:01 pmSWF - MIA
3 stops30h 43mMultiple Airlines
jue. 11/63:04 pmMIA - SWF
2 stops19h 37mMultiple Airlines
Deal found 10/27$342

Cheap 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 octubre 29, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$230
(Kiwi.com)

One-way from

$109
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$221
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. 9% potential increase in price ($22 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 October 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 octubre 29, 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

vie. 11/21

11:12 am-1:29 pm

1 stop26h 17m

Key West

lun. 11/24

8:55 am-8:53 am

1 stop23h 58m

$230

New WindsorMiami

SWF - MIA

SWFMIA

New Windsor Stewart

vie. 1/30

11:09 am-11:30 am

2 stops24h 21m

Miami

dom. 2/1

6:00 am-10:19 am

2 stops28h 19m

$249

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

dom. 12/7

11:43 am-8:15 am

1 stop20h 32m

Key West

dom. 12/14

12:20 pm-11:37 am

1 stop23h 17m

$252

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

jue. 1/8

10:48 am-9:37 pm

1 stop10h 49m

Key West

dom. 1/11

3:46 pm-6:43 pm

1 stop26h 57m

$257

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

dom. 1/4

10:49 am-9:47 pm

1 stop10h 58m

Key West

jue. 1/8

3:46 pm-6:43 pm

1 stop26h 57m

$258

New WindsorMiami

SWF - MIA

SWFMIA

New Windsor Stewart

vie. 1/23

11:09 am-11:30 am

2 stops24h 21m

Miami

dom. 1/25

11:28 am-10:19 am

2 stops22h 51m

$259

New WindsorMiami

SWF - MIA

SWFMIA

New Windsor Stewart

vie. 11/14

11:01 am-9:58 am

2 stops22h 57m

Miami

dom. 11/23

6:46 am-10:07 am

2 stops27h 21m

$269

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

jue. 1/22

10:48 am-9:37 pm

1 stop10h 49m

Key West

dom. 1/25

9:46 am-11:31 am

2 stops25h 45m

$286

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

mar. 11/11

11:16 am-9:11 am

1 stop21h 55m

Key West

lun. 11/17

4:47 pm-10:26 am

1 stop17h 39m

$287

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

dom. 1/4

11:43 am-12:30 pm

1 stop24h 47m

Key West

mié. 1/7

4:06 pm-9:58 am

1 stop17h 52m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 30 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 $155). 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 $155). 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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