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$99+ 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 7/27. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — EYW
Jul 23 — Jul 301
Wed 7/23
Wed 7/30
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 July 18, 2025.

Round-trip from

$237
(Kiwi.com)

One-way from

$99
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$424
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 ($5 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% 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 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 July 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/17. 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 9/1111:33 amSWF - EYW
1 stop24h 19mBreeze Airways
Sun 9/148:55 amEYW - SWF
2 stops26h 49mBreeze Airways
Deal found 7/17$237
This Mytrip deal was found by Cheapflights users on 7/16. 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 10/306:16 pmSWF - EYW
1 stop13h 51mMultiple Airlines
Sun 11/212:32 pmEYW - SWF
2 stops22h 39mMultiple Airlines
Deal found 7/16$363
This Mytrip deal was found by Cheapflights users on 7/17. 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.
Sat 12/209:45 amSWF - EYW
2 stops23h 24mAllegiant Air
Sat 12/2710:35 pmEYW - SWF
1 stop11h 24mAllegiant Air
Deal found 7/17$571

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 July 18, 2025.
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

Thu 9/11

11:33 am-11:52 am

1 stop24h 19m

Key West

Sun 9/14

8:55 am-11:44 am

2 stops26h 49m

$237

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

$517

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 8/7

8:03 pm-3:18 pm

2 stops19h 15m

Key West

Sun 8/10

8:54 am-7:13 pm

1 stop10h 19m

$596

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 7/27

7:52 pm-1:07 pm

1 stop17h 15m

$99

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 8/14

8:33 pm-3:22 pm

2 stops18h 49m

$206

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Mon 9/1

1:55 pm-9:22 am

2 stops19h 27m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/15

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, August is the cheapest month in which you can book a flight from New Windsor to Key West (average of $328). Flying from New Windsor to Key West 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.

Reviews of airlines servicing Key West

Get insights into the airlines that provide service to Key West. 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 Key West. Reviews last updated July 18, 2025.
Get a feel of what it's like to fly with Breeze Airways and Allegiant Air from New Windsor to Key West by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.0
Very good
188 reviews

Boarding

8.3

Entertainment

6.6

Comfort

8.1

Crew

8.7

Overall

8.0

Food

6.7

Reviews

1 / 12
2.0
Mediocre

Andrew,Jul 2025

CHS - PWM

One word-AWFUL! If you can, avoid this airline like the plague! Rude gate supervisor-rude flight attendant AFTER they delayed the plane for 4 hours! Zero Fs given by them-only got real answers and genuine apologies from the pilots themselves. Febreeze, as I’m calling them, stinks!
Breeze Airways
8.0
Very good
188 reviews
Breeze Airways
8.0
Very good
188 reviews

Boarding

8.3

Entertainment

6.6

Comfort

8.1

Crew

8.7

Overall

8.0

Food

6.7

Reviews

1 / 12
2.0
Mediocre

Andrew,Jul 2025

CHS - PWM

One word-AWFUL! If you can, avoid this airline like the plague! Rude gate supervisor-rude flight attendant AFTER they delayed the plane for 4 hours! Zero Fs given by them-only got real answers and genuine apologies from the pilots themselves. Febreeze, as I’m calling them, stinks!
Allegiant Air
7.2
Good
702 reviews
Breeze Airways
8.0
Very good
188 reviews

Boarding

8.3

Entertainment

6.6

Comfort

8.1

Crew

8.7

Overall

8.0

Food

6.7

Reviews

1 / 12
2.0
Mediocre

Andrew,Jul 2025

CHS - PWM

One word-AWFUL! If you can, avoid this airline like the plague! Rude gate supervisor-rude flight attendant AFTER they delayed the plane for 4 hours! Zero Fs given by them-only got real answers and genuine apologies from the pilots themselves. Febreeze, as I’m calling them, stinks!

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.

  • 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, August is the cheapest month in which you can book a flight from New Windsor to Key West (average of $328). Flying from New Windsor to Key West 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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