HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Key West

$126+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — EYW
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to Key West with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/26. 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.
Sun 8/3010:33 am
SWF
-
EYW
1 stop24h 54m
Breeze Airways
Fri 9/2511:59 am
EYW
-
SWF
1 stop23h 40m
Breeze Airways
Deal found 7/26$196
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/2710:33 am
SWF
-
EYW
1 stop24h 54m
Breeze Airways
Mon 8/3112:07 pm
EYW
-
SWF
1 stop23h 01m
Breeze Airways
Deal found 7/22$217
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
Wed 8/2612:05 pm
SWF
-
EYW
2 stops23h 20m
Breeze Airways
Mon 8/3112:07 pm
EYW
-
SWF
1 stop23h 01m
Breeze Airways
Deal found 7/25$266
This Kiwi.com deal was found by Cheapflights users on 7/26. 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.
Sun 10/187:14 pm
SWF
-
EYW
1 stop24h 20m
Allegiant Air
Thu 10/228:36 pm
EYW
-
SWF
1 stop20h 13m
Allegiant Air
Deal found 7/26$268
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 8/2912:05 pm
SWF
-
EYW
2 stops22h 19m
Multiple Airlines
Sat 9/53:48 pm
EYW
-
SWF
1 stop18h 35m
Multiple Airlines
Deal found 7/24$269
This Kiwi.com deal was found by Cheapflights users on 7/26. 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.
Sat 9/1912:39 pm
SWF
-
EYW
2 stops22h 56m
Multiple Airlines
Thu 9/246:11 pm
EYW
-
SWF
1 stop16h 05m
Multiple Airlines
Deal found 7/26$276
This Kiwi.com deal was found by Cheapflights users on 7/26. 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.
Fri 9/1812:16 pm
SWF
-
EYW
2 stops21h 08m
Breeze Airways
Fri 9/2511:59 am
EYW
-
SWF
1 stop23h 40m
Breeze Airways
Deal found 7/26$277

Find 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 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$196
(Kiwi.com)

One-way from

$126
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$484
Provider with most accurate pricing for New Windsor Stewart-Key West flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-Key West flights.
Search Deals
From New Windsor Stewart to Key West
Search Deals
One-way flight from New Windsor Stewart to Key West
Search Deals
High demand for flights, 1% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

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 27, 2026.
Use the filters below to find and compare flights from New Windsor to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 8/30

10:33 am-11:27 am

1 stop24h 54m

Key West

Fri 9/25

12:59 pm-11:39 am

2 stops22h 40m

$205

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 9/13

10:56 am-10:19 am

1 stop23h 23m

Key West

Wed 9/23

12:53 pm-10:23 am

1 stop21h 30m

$291
Quickest round-trip

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 10/1

7:36 pm-3:26 pm

1 stop19h 50m

Key West

Mon 10/5

9:24 am-6:23 pm

1 stop8h 59m

$308

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Fri 12/4

12:16 pm-10:04 am

2 stops21h 48m

Key West

Wed 12/9

4:40 pm-9:48 am

1 stop17h 08m

$320

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 10/22

10:38 am-12:19 pm

2 stops25h 41m

Key West

Mon 10/26

9:34 am-6:11 pm

1 stop8h 37m

$329

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 10/18

11:53 am-12:19 pm

2 stops24h 26m

Key West

Thu 10/22

8:36 pm-4:49 pm

1 stop20h 13m

$340

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 10/22

4:59 pm-1:13 pm

1 stop20h 14m

Key West

Wed 10/28

12:52 pm-4:09 pm

1 stop27h 17m

$347

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 8/16

6:39 pm-12:34 pm

2 stops41h 55m

Key West

Sat 8/22

3:52 pm-10:27 am

1 stop18h 35m

$398

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 11/29

8:36 am-10:19 am

1 stop25h 43m

Key West

Thu 12/3

12:10 pm-8:52 am

2 stops20h 42m

$457

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 8/6

10:33 am-11:27 am

1 stop24h 54m

Key West

Sun 8/9

10:56 am-11:08 am

2 stops48h 12m

$504

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

Showing 1-10 of 23 resultsSorted by cheapest first
1
2
3

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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Windsor-Key West flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

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 50m. 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Stewart to Key West

See prices for flight routes from nearby airports that may be better suited for you.
Newark to Orlando flights
LaGuardia to Miami flights
Newark to Miami flights
LaGuardia to Orlando flights
John F Kennedy Intl to Orlando flights
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Miami flights
Newark to Fort Lauderdale flights
LaGuardia to Fort Lauderdale flights
Newark to Tampa flights
LaGuardia to West Palm Beach flights
John F Kennedy Intl to Tampa flights
LaGuardia to Tampa flights
Newark to West Palm Beach flights
White Plains to Orlando flights
Newark to Fort Myers flights
Newark to Jacksonville flights
John F Kennedy Intl to Fort Myers flights
Newark to Sarasota flights
John F Kennedy Intl to Sarasota flights
Buffalo to Orlando flights
John F Kennedy Intl to Jacksonville flights
LaGuardia to Fort Myers flights
Syracuse to Orlando flights
LaGuardia to Sarasota flights
LaGuardia to Jacksonville flights
White Plains to Tampa flights
Stewart to Orlando flights
Islip to Orlando flights
Newark to Key West flights
Albany to Orlando flights
Rochester to Orlando flights
Stewart to Fort Lauderdale flights
White Plains to Fort Lauderdale flights
Stewart to Tampa flights
Buffalo to Fort Lauderdale flights
John F Kennedy Intl to Key West flights
John F Kennedy Intl to Daytona Beach flights
White Plains to Fort Myers flights
Stewart to Fort Myers flights
Buffalo to Tampa flights
LaGuardia to Pensacola flights
Newark to Pensacola flights
Buffalo to Miami flights
Newark to Daytona Beach flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.