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$236+ 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 7/7. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — NAP
may. 5 — may. 121
lun. 5/5
lun. 5/12
1 adult, Economy
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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 abril 30, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$492
(Mytrip)

One-way from

$236
(Connections by easyJet)

Popular in

June

Cheapest in

January

Average price

$672
Provider with most accurate pricing for New York (NYC)-Rome (ROM) flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Rome (ROM) flights.
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From New Windsor Stewart to Italy
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One-way flight from New Windsor Stewart to Italy
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Highest demand for flights based on searches. 13% potential increase in price ($110 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 abril 30, 2025.

This PLAY deal was found by Cheapflights users on 4/29. 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 PLAY is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/17:15 pmSWF - MXP
2 stops14h 50mMultiple Airlines
mar. 10/79:00 amMXP - SWF
2 stops15h 05mMultiple Airlines
Deal found 4/29$486
This Mytrip deal was found by Cheapflights users on 4/28. 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.
mar. 5/67:15 pmSWF - FCO
2 stops21h 05mMultiple Airlines
jue. 5/810:55 pmFCO - SWF
2 stops25h 10mMultiple Airlines
Deal found 4/28$517
This PLAY deal was found by Cheapflights users on 4/28. 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 PLAY is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/67:15 pmSWF - LIN
2 stops21h 20mMultiple Airlines
mar. 8/267:00 amLIN - SWF
2 stops17h 05mMultiple Airlines
Deal found 4/28$536
This Mytrip deal was found by Cheapflights users on 4/28. 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.
lun. 5/57:15 pmSWF - BGY
2 stops23h 15mMultiple Airlines
lun. 5/123:10 pmBGY - SWF
2 stops32h 55mMultiple Airlines
Deal found 4/28$552
This Mytrip deal was found by Cheapflights users on 4/29. 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.
dom. 5/117:15 pmSWF - CIA
2 stops20h 40mMultiple Airlines
sáb. 5/176:25 amCIA - SWF
2 stops17h 40mMultiple Airlines
Deal found 4/29$556
This Mytrip deal was found by Cheapflights users on 4/28. 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.
lun. 5/57:15 pmSWF - VCE
2 stops19h 50mMultiple Airlines
jue. 5/87:30 pmVCE - SWF
2 stops28h 35mMultiple Airlines
Deal found 4/28$570
This Mytrip deal was found by Cheapflights users on 4/29. 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.
lun. 5/57:15 pmSWF - NAP
2 stops16h 45mMultiple Airlines
dom. 5/111:30 pmNAP - SWF
2 stops34h 35mMultiple Airlines
Deal found 4/29$626
This Mytrip deal was found by Cheapflights users on 4/29. 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.
mar. 5/137:15 pmSWF - FLR
3 stops21h 40mMultiple Airlines
vie. 5/167:00 pmFLR - SWF
3 stops29h 05mMultiple Airlines
Deal found 4/29$715
This Mytrip deal was found by Cheapflights users on 4/28. 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.
sáb. 6/77:15 pmSWF - BLQ
3 stops17h 40mMultiple Airlines
dom. 6/157:45 amBLQ - SWF
2 stops16h 20mMultiple Airlines
Deal found 4/28$773
This Mytrip deal was found by Cheapflights users on 4/28. 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.
vie. 5/27:15 pmSWF - CTA
2 stops18h 15mMultiple Airlines
dom. 5/47:40 pmCTA - SWF
2 stops28h 25mMultiple Airlines
Deal found 4/28$891

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 abril 30, 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 - MXP

SWFMXP

New Windsor Stewart

mié. 10/1

7:15 pm-4:05 pm

2 stops14h 50m

Milan Malpensa

mar. 10/7

9:00 am-6:05 pm

2 stops15h 05m

$486

New WindsorRome

SWF - FCO

SWFFCO

New Windsor Stewart

mar. 5/6

7:15 pm-10:20 pm

2 stops21h 05m

Rome Fiumicino

jue. 5/8

10:55 pm-6:05 pm

2 stops25h 10m

$517

New WindsorMilan

SWF - LIN

SWFLIN

New Windsor Stewart

mié. 8/6

7:15 pm-10:35 pm

2 stops21h 20m

Milan Linate

mar. 8/26

7:00 am-6:05 pm

2 stops17h 05m

$536

New WindsorRome

SWF - CIA

SWFCIA

New Windsor Stewart

dom. 5/11

7:15 pm-9:55 pm

2 stops20h 40m

Rome Ciampino

sáb. 5/17

6:25 am-6:05 pm

2 stops17h 40m

$556

New WindsorVenice

SWF - VCE

SWFVCE

New Windsor Stewart

lun. 5/5

7:15 pm-9:05 pm

2 stops19h 50m

Venice Marco Polo

jue. 5/8

7:30 pm-6:05 pm

2 stops28h 35m

$570

New WindsorBergamo

SWF - BGY

SWFBGY

New Windsor Stewart

mié. 5/14

7:15 pm-12:05 am

2 stops22h 50m

Bergamo Orio Al Serio

dom. 5/18

4:35 pm-6:05 pm

2 stops31h 30m

$577

New WindsorNaples

SWF - NAP

SWFNAP

New Windsor Stewart

lun. 5/5

7:15 pm-6:00 pm

2 stops16h 45m

Naples

dom. 5/11

1:30 pm-6:05 pm

2 stops34h 35m

$626

New WindsorFlorence

SWF - FLR

SWFFLR

New Windsor Stewart

mar. 5/13

7:15 pm-10:55 pm

3 stops21h 40m

Florence Peretola

vie. 5/16

7:00 pm-6:05 pm

3 stops29h 05m

$715

New WindsorBologna

SWF - BLQ

SWFBLQ

New Windsor Stewart

sáb. 6/7

7:15 pm-6:55 pm

3 stops17h 40m

Bologna Guglielmo Marconi

dom. 6/15

7:45 am-6:05 pm

2 stops16h 20m

$773

New WindsorCatania

SWF - CTA

SWFCTA

New Windsor Stewart

lun. 6/23

7:15 pm-7:00 pm

3 stops17h 45m

Catania Fontanarossa

lun. 6/30

7:55 pm-6:05 pm

2 stops28h 10m

$938

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 20 results
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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 $1,238). 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 Italy by month

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

In terms of precipitation, rainfall in Italy ranges from 0.6 - 4.4 inches per month. November is typically the wettest month, when rainfall can reach 4.4 in. June is typically the driest time to visit Italy when rainfall is around 0.6 in.

Temperature in Italy by month

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

If weather is an important factor for your trip to Italy, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 75.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 46.4 F).

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 - Milan Malpensa, New Windsor Stewart - Milan Linate and New Windsor Stewart - Rome Fiumicino.

  • 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 $1,238). 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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Alternative routes for Stewart to Italy

See prices for flight routes from nearby airports that may be better suited for you.
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