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$69+ Cheap flights from New Windsor to Key West (SWF - EYW)

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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — EYW
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
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Cheap flight deals from Stewart to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Key West (EYW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$186
(Kiwi.com)

One-way from

$69
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$422
Provider with most accurate pricing for New Windsor Stewart-Key West flight deals.
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Provider most trusted by Cheapflights users for New Windsor Stewart-Key West flights.
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From New Windsor Stewart to Key West
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One-way flight from New Windsor Stewart to Key West
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Highest demand for flights based on searches. 1% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Stewart to Key West

Cheapest flights from Stewart to Key West
Explore the most affordable flight options available from Stewart to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 15, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
Sun 1/2512:13 pm
SWF
-
EYW
1 stop24h 13m
Multiple Airlines
Thu 2/53:46 pm
EYW
-
SWF
1 stop26h 57m
Multiple Airlines
Deal found 1/14$186
This Kiwi.com deal was found by Cheapflights users on 1/15. 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.
Sun 1/2512:13 pm
SWF
-
EYW
1 stop24h 13m
Multiple Airlines
Thu 1/293:46 pm
EYW
-
SWF
1 stop26h 57m
Multiple Airlines
Deal found 1/15$189
This Kiwi.com deal was found by Cheapflights users on 1/15. 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.
Sun 1/2512:13 pm
SWF
-
EYW
1 stop24h 13m
Breeze Airways
Thu 1/2910:06 am
EYW
-
SWF
2 stops25h 25m
Breeze Airways
Deal found 1/15$193
This Kiwi.com deal was found by Cheapflights users on 1/15. 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.
Sun 1/2512:13 pm
SWF
-
EYW
1 stop24h 13m
Multiple Airlines
Wed 1/284:06 pm
EYW
-
SWF
1 stop17h 52m
Multiple Airlines
Deal found 1/15$226
This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
Sun 1/2512:13 pm
SWF
-
EYW
1 stop24h 13m
Breeze Airways
Thu 2/59:46 am
EYW
-
SWF
2 stops25h 45m
Breeze Airways
Deal found 1/14$243
This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
Sun 2/227:28 pm
SWF
-
EYW
1 stop19h 19m
Allegiant Air
Thu 2/264:13 pm
EYW
-
SWF
1 stop18h 00m
Allegiant Air
Deal found 1/14$265
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 2/218:24 pm
SWF
-
EYW
1 stop17h 55m
Allegiant Air
Thu 2/264:13 pm
EYW
-
SWF
1 stop18h 00m
Allegiant Air
Deal found 1/15$282
This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
Thu 1/2212:13 pm
SWF
-
EYW
1 stop24h 13m
Multiple Airlines
Sun 1/2512:51 pm
EYW
-
SWF
1 stop21h 28m
Multiple Airlines
Deal found 1/14$321
This Kiwi.com deal was found by Cheapflights users on 1/15. 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.
Sun 2/2211:48 am
SWF
-
EYW
1 stop24h 38m
Breeze Airways
Thu 2/269:46 am
EYW
-
SWF
2 stops25h 45m
Breeze Airways
Deal found 1/15$335
This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
Sun 2/810:48 am
SWF
-
EYW
1 stop10h 49m
Allegiant Air
Thu 2/124:21 pm
EYW
-
SWF
1 stop17h 53m
Allegiant Air
Deal found 1/14$342

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Key West 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 January 15, 2026.
Use the filters below to find and compare flights from New Windsor to Key West that are best for you.

Fly from

Stewart

Fly to

Key West

Route

Depart

Return

Price

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 1/25

12:13 pm-12:26 pm

1 stop24h 13m

Key West

Thu 2/5

3:46 pm-6:43 pm

1 stop26h 57m

$186

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 1/25

12:13 pm-12:26 pm

1 stop24h 13m

Key West

Thu 1/29

3:46 pm-6:43 pm

1 stop26h 57m

$189

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 1/25

12:13 pm-12:26 pm

1 stop24h 13m

Key West

Thu 1/29

10:06 am-11:31 am

2 stops25h 25m

$194

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 1/25

12:13 pm-12:26 pm

1 stop24h 13m

Key West

Thu 2/5

9:46 am-11:31 am

2 stops25h 45m

$243

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 2/22

7:28 pm-2:47 pm

1 stop19h 19m

Key West

Thu 2/26

4:13 pm-10:13 am

1 stop18h 00m

$265

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sat 2/21

8:24 pm-2:19 pm

1 stop17h 55m

Key West

Thu 2/26

4:13 pm-10:13 am

1 stop18h 00m

$282

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 3/8

7:27 pm-2:53 pm

1 stop19h 26m

Key West

Thu 3/12

4:31 pm-9:02 am

1 stop16h 31m

$283

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 1/22

12:13 pm-12:26 pm

1 stop24h 13m

Key West

Sun 1/25

12:51 pm-10:19 am

1 stop21h 28m

$321

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 2/22

11:48 am-12:26 pm

1 stop24h 38m

Key West

Thu 2/26

9:46 am-11:31 am

2 stops25h 45m

$335

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 2/8

10:48 am-9:37 pm

1 stop10h 49m

Key West

Thu 2/12

4:21 pm-10:14 am

1 stop17h 53m

$342

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/15

Showing 1-10 of 23 results
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Compare providers for flights from Stewart to Key West

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Stewart to Key West in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on New Windsor-Key West flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on New Windsor-Key West flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from New Windsor-Key West flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Key West flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New Windsor-Key West flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Stewart to Key West

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

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

Currently, May is the cheapest month in which you can book a flight from New Windsor to Key West (average of $134). Flying from New Windsor to Key West 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 Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from New Windsor to Key West?

    Departing from New Windsor to Key West will take you 19h 19m. New Windsor and Key West are separated by a distance of 1250 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

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

  • How can I find direct flights from Stewart to Key West?

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

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

    Yes. Cheapflights offers flight deals from Stewart to Key West 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 Key West?

    Currently, May is the cheapest month in which you can book a flight from New Windsor to Key West (average of $134). Flying from New Windsor to Key West 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

Browse thousands of different options on Cheapflights for your next trip

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