HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Italy

$168+ Cheap flights from New Windsor (SWF) to Italy

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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — NAP
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to Italy 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 Italy

Keep the following information in mind while searching for Stewart to Italy flight deals. Data was last updated July 29, 2025.

Round-trip from

$578
(PLAY)

One-way from

$168
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$760
From New Windsor Stewart to Italy
Search Deals
One-way flight from New Windsor Stewart to Italy
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($106 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

Find flight deals from Stewart to Italy

Cheapest flights from Stewart to Italy
Explore the most affordable flight options available from Stewart to Italy. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

This PLAY deal was found by Cheapflights users on 7/27. 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 PLAY is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/187:15 pmSWF - LIN
2 stops21h 20mMultiple Airlines
Tue 8/267:00 amLIN - SWF
2 stops17h 05mMultiple Airlines
Deal found 7/27$578
This PLAY deal was found by Cheapflights users on 7/27. 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 PLAY is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/117:15 pmSWF - FCO
2 stops21h 50mMultiple Airlines
Tue 8/266:40 amFCO - SWF
2 stops17h 25mMultiple Airlines
Deal found 7/27$601
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/57:15 pmSWF - MXP
1 stop15h 45mMultiple Airlines
Thu 8/287:30 amMXP - SWF
1 stop16h 35mMultiple Airlines
Deal found 7/29$606
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.
Sat 8/237:15 pmSWF - CIA
2 stops18h 05mMultiple Airlines
Thu 8/286:00 amCIA - SWF
2 stops18h 05mMultiple Airlines
Deal found 7/29$755
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.
Tue 8/57:15 pmSWF - VCE
2 stops20h 10mMultiple Airlines
Tue 8/266:10 amVCE - SWF
2 stops17h 55mMultiple Airlines
Deal found 7/29$782
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/197:15 pmSWF - TSF
3 stops19h 15mMultiple Airlines
Wed 8/272:40 pmTSF - SWF
3 stops33h 25mMultiple Airlines
Deal found 7/28$803
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.
Tue 8/127:15 pmSWF - BGY
2 stops21h 20mMultiple Airlines
Sat 8/236:30 amBGY - SWF
2 stops17h 35mMultiple Airlines
Deal found 7/29$871
This PLAY deal was found by Cheapflights users on 7/27. 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 PLAY is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/217:15 pmSWF - NAP
2 stops17h 30mMultiple Airlines
Mon 8/257:20 amNAP - SWF
2 stops16h 45mMultiple Airlines
Deal found 7/27$952

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Italy 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 29, 2025.
Use the filters below to find and compare flights from New Windsor to Italy that are best for you.

Fly from

Stewart

Fly to

Italy

Route

Depart

Return

Price

New WindsorMilan

SWF - LIN

SWFLIN

New Windsor Stewart

Mon 8/18

7:15 pm-10:35 pm

2 stops21h 20m

Milan Linate

Tue 8/26

7:00 am-6:05 pm

2 stops17h 05m

$578

New WindsorRome

SWF - FCO

SWFFCO

New Windsor Stewart

Mon 8/11

7:15 pm-11:05 pm

2 stops21h 50m

Rome Fiumicino

Tue 8/26

6:40 am-6:05 pm

2 stops17h 25m

$601

New WindsorMilan

SWF - MXP

SWFMXP

New Windsor Stewart

Tue 8/5

7:15 pm-5:00 pm

1 stop15h 45m

Milan Malpensa

Thu 8/28

7:30 am-6:05 pm

1 stop16h 35m

$606

New WindsorRome

SWF - CIA

SWFCIA

New Windsor Stewart

Sat 8/23

7:15 pm-7:20 pm

2 stops18h 05m

Rome Ciampino

Thu 8/28

6:00 am-6:05 pm

2 stops18h 05m

$755

New WindsorVenice

SWF - VCE

SWFVCE

New Windsor Stewart

Tue 8/5

7:15 pm-9:25 pm

2 stops20h 10m

Venice Marco Polo

Tue 8/26

6:10 am-6:05 pm

2 stops17h 55m

$782

New WindsorVenice

SWF - TSF

SWFTSF

New Windsor Stewart

Tue 8/19

7:15 pm-8:30 pm

3 stops19h 15m

Venice Treviso A. Canova

Wed 8/27

2:40 pm-6:05 pm

3 stops33h 25m

$803

New WindsorBergamo

SWF - BGY

SWFBGY

New Windsor Stewart

Tue 8/12

7:15 pm-10:35 pm

2 stops21h 20m

Bergamo Orio Al Serio

Sat 8/23

6:30 am-6:05 pm

2 stops17h 35m

$871

New WindsorNaples

SWF - NAP

SWFNAP

New Windsor Stewart

Thu 8/21

7:15 pm-6:45 pm

2 stops17h 30m

Naples

Mon 8/25

7:20 am-6:05 pm

2 stops16h 45m

$952

New WindsorMilan

SWF - MXP

SWFMXP

New Windsor Stewart

Wed 8/6

7:15 pm-1:10 am

1 stop23h 55m

$168

New WindsorRome

SWF - FCO

SWFFCO

New Windsor Stewart

Wed 8/6

7:15 pm-9:40 pm

2 stops44h 25m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 18 results
1
2

Best time to book a flight from Stewart to Italy

Have a flexible travel schedule? Discover the best time to fly to Italy 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 Italy

What is the cheapest month to book a flight from New Windsor to Italy?

Currently, January is the cheapest month in which you can book a flight from New Windsor to Italy (average of $703). Flying from New Windsor to Italy in June is currently the most expensive (average of $1,210). 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 Italy. 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 Italy?

    Most people fly from New Windsor Stewart (SWF) if they book a flight from New Windsor to Italy. New Windsor Stewart is conveniently located just 4.3 mi from New Windsor’s city center.

  • What are the most popular routes from New Windsor to Italy?

    The most popular flight routes from New Windsor to Italy are New Windsor Stewart - Rome Fiumicino, New Windsor Stewart - Milan Malpensa and New Windsor Stewart - Milan Linate.

  • Can I find deals for flights from Stewart to Italy that include hotel bookings?

    Yes. In addition to deals on Stewart to Italy flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Stewart to Italy?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Italy.

  • Can I find deals for business class flights from Stewart to Italy?

    Yes. Cheapflights offers flight deals from Stewart to Italy 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 Italy?

    Currently, January is the cheapest month in which you can book a flight from New Windsor to Italy (average of $703). Flying from New Windsor to Italy in June is currently the most expensive (average of $1,210). 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 Italy

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Heathrow flights
Newark to Heathrow flights
John F Kennedy Intl to Charles de Gaulle flights
John F Kennedy Intl to Leonardo da Vinci/Fiumicino flights
John F Kennedy Intl to London City flights
John F Kennedy Intl to Gatwick flights
Newark to Gatwick flights
Newark to Charles de Gaulle flights
LaGuardia to Heathrow flights
Newark to Leonardo da Vinci/Fiumicino flights
John F Kennedy Intl to Istanbul flights
Newark to London City flights
John F Kennedy Intl to Stansted flights
LaGuardia to Gatwick flights
John F Kennedy Intl to Lisbon flights
Newark to Stansted flights
Newark to Athens flights
Newark to Lisbon flights
Newark to Orly flights
John F Kennedy Intl to Orly flights
Newark to Barcelona-El Prat flights
Newark to Dublin flights
John F Kennedy Intl to Dublin flights
John F Kennedy Intl to Barcelona-El Prat flights
Newark to Madrid flights
John F Kennedy Intl to Luton flights
John F Kennedy Intl to Athens flights
LaGuardia to Charles de Gaulle flights
Newark to Luton flights
John F Kennedy Intl to Madrid flights
John F Kennedy Intl to Malpensa flights
John F Kennedy Intl to Amsterdam flights
Newark to Malpensa flights
LaGuardia to Leonardo da Vinci/Fiumicino flights
John F Kennedy Intl to Frankfurt flights
John F Kennedy Intl to Frederic Chopin flights
Newark to Amsterdam flights
Newark to Frankfurt flights
John F Kennedy Intl to Keflavik Intl flights
LaGuardia to Istanbul flights
John F Kennedy Intl to Vicenza flights
John F Kennedy Intl to Zurich flights
Newark to Istanbul flights
LaGuardia to Lisbon flights
Newark to Keflavik Intl flights
John F Kennedy Intl to Munich flights
LaGuardia to Madrid flights
John F Kennedy Intl to Naples flights
Newark to Zurich flights
LaGuardia to Barcelona-El Prat 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.