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Florida Keys

$98+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — EYW
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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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 July 30, 2025.

Round-trip from

$189
(Kiwi.com)

One-way from

$98
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$239
From New Windsor Stewart to Florida Keys
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One-way flight from New Windsor Stewart to Florida Keys
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Highest demand for flights based on searches. 10% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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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 July 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
Sat 8/97:29 pmSWF - EYW
1 stop17h 38mBreeze Airways
Mon 8/1110:02 amEYW - SWF
1 stop25h 54mBreeze Airways
Deal found 7/28$189
This Mytrip deal was found by Cheapflights users on 7/30. 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.
Fri 10/2411:31 amSWF - MIA
2 stops24h 42mMultiple Airlines
Sun 10/267:01 pmMIA - SWF
2 stops19h 10mMultiple Airlines
Deal found 7/30$246
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:14 pmSWF - EYW
1 stop13h 57mAllegiant Air
Mon 11/1710:41 amEYW - SWF
2 stops23h 45mAllegiant Air
Deal found 7/29$372
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/177:03 pmSWF - EYW
2 stops18h 04mMultiple Airlines
Thu 8/2110:02 amEYW - SWF
1 stop9h 10mMultiple Airlines
Deal found 7/29$515

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 July 30, 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

Sat 8/9

7:29 pm-1:07 pm

1 stop17h 38m

Key West

Mon 8/11

10:02 am-11:56 am

1 stop25h 54m

$189

New WindsorMiami

SWF - MIA

SWFMIA

New Windsor Stewart

Fri 10/24

11:31 am-12:13 pm

2 stops24h 42m

Miami

Sun 10/26

7:01 pm-2:11 pm

2 stops19h 10m

$246

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 8/17

7:03 pm-1:07 pm

2 stops18h 04m

Key West

Thu 8/21

10:02 am-7:12 pm

1 stop9h 10m

$515

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 8/14

8:33 pm-9:33 am

1 stop13h 00m

Key West

Sun 8/17

8:53 am-7:43 pm

1 stop10h 50m

$517

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sat 8/30

7:29 pm-1:07 pm

1 stop17h 38m

$98

New WindsorMiami

SWF - MIA

SWFMIA

New Windsor Stewart

Fri 10/3

12:11 pm-12:21 pm

2 stops24h 10m

$123

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 8/14

8:33 pm-9:33 am

1 stop13h 00m

$170

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 8/17

7:03 pm-1:07 pm

2 stops18h 04m

$253

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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, August is the cheapest month in which you can book a flight from New Windsor to Florida Keys (average of $328). Flying from New Windsor to Florida Keys in March is currently the most expensive (average of $492). 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.

Reviews of airlines servicing Florida Keys

Get insights into the airlines that provide service to Florida Keys. 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 Keys. Reviews last updated July 30, 2025.
Read reviews from past customers who have flown Breeze Airways and Allegiant Air from New Windsor to Florida Keys. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.0
Very good
191 reviews

Comfort

8.1

Crew

8.7

Food

6.7

Overall

8.0

Entertainment

6.5

Boarding

8.2

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.0
Very good
191 reviews
Breeze Airways
8.0
Very good
191 reviews

Comfort

8.1

Crew

8.7

Food

6.7

Overall

8.0

Entertainment

6.5

Boarding

8.2

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Allegiant Air
7.2
Good
703 reviews
Breeze Airways
8.0
Very good
191 reviews

Comfort

8.1

Crew

8.7

Food

6.7

Overall

8.0

Entertainment

6.5

Boarding

8.2

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

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.

  • 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, August is the cheapest month in which you can book a flight from New Windsor to Florida Keys (average of $328). Flying from New Windsor to Florida Keys in March is currently the most expensive (average of $492). 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.

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