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$118+ 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
Jun 20 — Jun 271
Fri 6/20
Fri 6/27
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 June 15, 2025.

Round-trip from

$233
(Kiwi.com)

One-way from

$118
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$217
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. 9% potential increase in price ($24 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 June 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 June 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/13. 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 6/227:52 pmSWF - EYW
1 stop17h 25mBreeze Airways
Thu 6/2610:12 amEYW - SWF
1 stop9h 00mBreeze Airways
Deal found 6/13$233
This Mytrip deal was found by Cheapflights users on 6/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/307:00 pmSWF - EYW
1 stop21h 45mAllegiant Air
Wed 8/64:00 pmEYW - SWF
1 stop27h 13mAllegiant Air
Deal found 6/15$292
This Mytrip deal was found by Cheapflights users on 6/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/257:56 pmSWF - MIA
2 stops24h 08mMultiple Airlines
Thu 7/3111:10 amMIA - SWF
2 stops31h 56mMultiple Airlines
Deal found 6/14$322
This Mytrip deal was found by Cheapflights users on 6/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/36:42 pmSWF - EYW
2 stops18h 25mMultiple Airlines
Wed 8/64:00 pmEYW - SWF
1 stop27h 13mMultiple Airlines
Deal found 6/14$408

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 June 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

Sun 6/29

7:52 pm-1:17 pm

1 stop17h 25m

Key West

Thu 7/3

10:02 am-7:12 pm

1 stop9h 10m

$247

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Wed 7/30

7:00 pm-4:45 pm

1 stop21h 45m

Key West

Wed 8/6

4:00 pm-7:13 pm

1 stop27h 13m

$292

New WindsorMiami

SWF - MIA

SWFMIA

New Windsor Stewart

Fri 7/25

7:56 pm-8:04 pm

2 stops24h 08m

Miami

Thu 7/31

11:10 am-7:06 pm

2 stops31h 56m

$322

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 8/3

6:42 pm-1:07 pm

2 stops18h 25m

Key West

Wed 8/6

4:00 pm-7:13 pm

1 stop27h 13m

$408

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sat 8/30

7:29 pm-1:07 pm

1 stop17h 38m

$118

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Wed 7/16

7:00 pm-4:45 pm

1 stop21h 45m

$142

New WindsorMiami

SWF - MIA

SWFMIA

New Windsor Stewart

Mon 7/7

7:56 pm-6:00 pm

2 stops22h 04m

$163

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Wed 7/2

11:50 am-11:41 am

2 stops23h 51m

$211

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/14

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 $493). 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.

Rainfall in Florida Keys by month

Plan your trip to Florida Keys by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Florida Keys ranges from 1.6 - 9.9 inches per month. September is typically the wettest month, when rainfall can reach 9.9 in. January is typically the driest time to visit Florida Keys when rainfall is around 1.6 in.

Temperature in Florida Keys by month

Plan your trip to Florida Keys by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Florida Keys, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 68.0 F).

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 June 15, 2025.
Breeze Airways
8.1
Very good
179 reviews

Entertainment

6.6

Overall

8.1

Food

6.7

Comfort

8.2

Boarding

8.3

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
179 reviews
Breeze Airways
8.1
Very good
179 reviews

Entertainment

6.6

Overall

8.1

Food

6.7

Comfort

8.2

Boarding

8.3

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Allegiant Air
7.3
Good
722 reviews
Breeze Airways
8.1
Very good
179 reviews

Entertainment

6.6

Overall

8.1

Food

6.7

Comfort

8.2

Boarding

8.3

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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 $493). 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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