HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Key West

$134+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — EYW
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
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

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 septiembre 11, 2025.

Round-trip from

$331
(Kiwi.com)

One-way from

$134
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$371
From New Windsor Stewart to Key West
Search Deals
One-way flight from New Windsor Stewart to Key West
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 septiembre 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
jue. 12/1111:09 amSWF - EYW
1 stop10h 28mMultiple Airlines
dom. 12/142:25 pmEYW - SWF
1 stop21h 12mMultiple Airlines
Deal found 9/11$271
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
dom. 10/267:11 pmSWF - EYW
1 stop14h 06mMultiple Airlines
lun. 10/279:03 pmEYW - SWF
1 stop13h 23mMultiple Airlines
Deal found 9/11$340
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
jue. 10/237:11 pmSWF - EYW
1 stop14h 06mMultiple Airlines
lun. 10/279:03 pmEYW - SWF
1 stop13h 23mMultiple Airlines
Deal found 9/11$346
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
jue. 10/167:11 pmSWF - EYW
1 stop13h 01mAllegiant Air
lun. 10/203:56 pmEYW - SWF
1 stop18h 30mAllegiant Air
Deal found 9/10$351
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
vie. 10/1711:31 amSWF - EYW
2 stops48h 11mAllegiant Air
lun. 10/279:03 pmEYW - SWF
1 stop13h 23mAllegiant Air
Deal found 9/10$362
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
jue. 10/97:11 pmSWF - EYW
1 stop14h 06mMultiple Airlines
lun. 10/133:56 pmEYW - SWF
1 stop18h 30mMultiple Airlines
Deal found 9/11$369
This Mytrip deal was found by Cheapflights users on 9/11. 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.
jue. 10/97:11 pmSWF - EYW
1 stop13h 01mAllegiant Air
jue. 10/1612:32 pmEYW - SWF
2 stops22h 09mAllegiant Air
Deal found 9/11$376
This Mytrip deal was found by Cheapflights users on 9/11. 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.
jue. 10/27:11 pmSWF - EYW
1 stop12h 11mMultiple Airlines
dom. 10/510:54 amEYW - SWF
2 stops23h 17mMultiple Airlines
Deal found 9/11$389
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
dom. 11/96:14 pmSWF - EYW
1 stop15h 37mMultiple Airlines
vie. 11/142:25 pmEYW - SWF
2 stops46h 17mMultiple Airlines
Deal found 9/10$400
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
dom. 12/2111:43 amSWF - EYW
1 stop24h 47mMultiple Airlines
lun. 12/2910:01 pmEYW - SWF
1 stop17h 59mMultiple Airlines
Deal found 9/11$430
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
mié. 12/245:34 pmSWF - EYW
1 stop14h 41mMultiple Airlines
lun. 12/2910:01 pmEYW - SWF
1 stop17h 59mMultiple Airlines
Deal found 9/11$434
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
dom. 12/2111:43 amSWF - EYW
1 stop24h 47mMultiple Airlines
mar. 12/303:15 pmEYW - SWF
1 stop25h 29mMultiple Airlines
Deal found 9/11$441

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 septiembre 11, 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

vie. 10/17

11:31 am-11:42 am

2 stops48h 11m

Key West

lun. 10/27

9:03 pm-10:26 am

1 stop13h 23m

$362

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

jue. 10/9

7:11 pm-8:12 am

1 stop13h 01m

Key West

jue. 10/16

12:32 pm-10:41 am

2 stops22h 09m

$376

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

jue. 10/2

7:11 pm-7:22 am

1 stop12h 11m

Key West

dom. 10/5

10:54 am-10:11 am

2 stops23h 17m

$389

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

lun. 11/24

10:57 am-9:35 am

2 stops22h 38m

Key West

vie. 11/28

5:58 pm-10:46 am

1 stop16h 48m

$480

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

jue. 11/27

11:43 am-8:15 am

1 stop20h 32m

Key West

dom. 11/30

3:30 pm-9:06 am

1 stop17h 36m

$548

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

dom. 10/26

11:43 am-8:15 am

1 stop20h 32m

Key West

jue. 10/30

8:55 am-11:44 am

2 stops26h 49m

$559

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

vie. 10/17

12:24 pm-10:07 am

2 stops21h 43m

Key West

lun. 10/20

3:56 pm-10:26 am

1 stop18h 30m

$595

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

vie. 10/31

12:24 pm-10:07 am

2 stops21h 43m

Key West

dom. 11/2

8:55 am-11:44 am

2 stops26h 49m

$601

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

vie. 11/14

12:24 pm-10:07 am

2 stops21h 43m

Key West

lun. 11/17

4:47 pm-10:26 am

1 stop17h 39m

$602

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

vie. 11/21

12:24 pm-10:07 am

2 stops21h 43m

Key West

lun. 11/24

8:55 am-8:53 am

1 stop23h 58m

$681

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 24 results
1
2
3

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 $491). 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 48h 11m. New Windsor and Key West are separated by a distance of 1250 mi.

  • 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 $491). 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

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.
John F Kennedy Intl to Miami flights
Newark to Fort Lauderdale flights
Newark to Miami flights
LaGuardia to Fort Lauderdale flights
LaGuardia to Miami flights
John F Kennedy Intl to Orlando flights
John F Kennedy Intl to Fort Lauderdale flights
Newark to Orlando flights
LaGuardia to Orlando flights
LaGuardia to Tampa flights
John F Kennedy Intl to West Palm Beach flights
Newark to Tampa flights
John F Kennedy Intl to Tampa flights
Newark to West Palm Beach flights
LaGuardia to West Palm Beach flights
Islip to Orlando flights
Newark to Fort Myers flights
John F Kennedy Intl to Fort Myers flights
Buffalo to Orlando flights
White Plains to Orlando flights
John F Kennedy Intl to Sarasota flights
LaGuardia to Fort Myers flights
John F Kennedy Intl to Jacksonville flights
Newark to Jacksonville flights
Syracuse to Orlando flights
Newark to Sarasota flights
Newark to Key West flights
Buffalo to Fort Lauderdale flights
LaGuardia to Jacksonville flights
Albany to Orlando flights
LaGuardia to Sarasota flights
Stewart to Orlando flights
White Plains to Fort Lauderdale flights
Rochester to Orlando flights
White Plains to West Palm Beach flights
John F Kennedy Intl to Key West flights
Stewart to Fort Lauderdale flights
Islip to West Palm Beach flights
White Plains to Miami flights
White Plains to Fort Myers flights
Islip to Tampa flights
Islip to Fort Lauderdale flights
White Plains to Tampa flights
LaGuardia to Pensacola flights
Buffalo to Miami flights
Rochester to Fort Lauderdale flights
Buffalo to Tampa flights
LaGuardia to Key West flights
Albany to Fort Lauderdale flights
Islip to Fort Myers 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.