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$502+ Cheap flights from Portland, ME (PWM) to Italy

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — NAP
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Portland to Italy

Cheapest flights from Portland to Italy
Explore the most affordable flight options available from Portland to Italy. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This Air Canada deal was found by Cheapflights users on 12/11. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/189:30 amPWM - MXP
2 stops18h 25mMultiple Airlines
Fri 12/261:05 pmMXP - PWM
3 stops30h 34mMultiple Airlines
Deal found 12/11$1,862
This Delta deal was found by Cheapflights users on 12/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/182:34 pmPWM - MXP
2 stops18h 21mDelta
Fri 12/2612:00 pmMXP - PWM
1 stop30h 20mDelta
Deal found 12/10$1,964
This Air Canada deal was found by Cheapflights users on 12/11. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:00 amPWM - MXP
3 stops21h 55mAir Canada
Fri 12/261:05 pmMXP - PWM
3 stops40h 17mAir Canada
Deal found 12/11$2,062
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/182:55 pmPWM - MXP
1 stop10h 35mUnited Airlines
Fri 12/269:45 amMXP - PWM
1 stop14h 26mUnited Airlines
Deal found 12/10$2,263

Find flight deals from Portland to Italy

Keep the following information in mind while searching for Portland to Italy flight deals. Data was last updated December 12, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$502
(Delta)

Popular in

June

Cheapest in

November

Average price

$721
Provider with most accurate pricing for Boston Logan Intl-Rome (ROM) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Rome (ROM) flights.
Search Deals
From Portland to Italy
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($117 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland 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 December 12, 2025.
Use the filters below to find and compare flights from Portland to Italy that are best for you.

Fly from

Portland

Fly to

Italy

Route

Depart

Return

Price

PortlandNaples

PWM - NAP

PWMNAP

Portland

Tue 3/10

2:30 pm-3:50 pm

2 stops20h 20m

Naples

Mon 3/16

6:15 am-12:10 am

2 stops22h 55m

$502

PortlandMilan

PWM - MXP

PWMMXP

Portland

Fri 1/23

2:35 pm-8:25 am

2 stops35h 50m

Milan Malpensa

Tue 1/27

9:15 am-12:20 am

2 stops21h 05m

$537

PortlandVenice

PWM - VCE

PWMVCE

Portland

Wed 1/28

6:16 am-10:30 am

2 stops22h 14m

Venice Marco Polo

Sun 2/1

11:05 am-12:20 am

2 stops43h 15m

$569

PortlandMilan

PWM - LIN

PWMLIN

Portland

Wed 2/4

9:40 am-11:55 am

2 stops20h 15m

Milan Linate

Sun 2/8

6:15 am-6:52 pm

2 stops18h 37m

$596

PortlandMilan

PWM - MXP

PWMMXP

Portland

Fri 1/23

9:40 am-10:45 am

2 stops19h 05m

Milan Malpensa

Tue 1/27

10:40 am-11:27 pm

2 stops18h 47m

$605

PortlandMilan

PWM - MXP

PWMMXP

Portland

Sat 1/10

2:35 pm-8:25 am

2 stops35h 50m

Milan Malpensa

Sat 1/17

9:15 am-11:59 pm

2 stops20h 44m

$623

PortlandMilan

PWM - MXP

PWMMXP

Portland

Sat 1/10

4:10 pm-4:40 pm

2 stops42h 30m

Milan Malpensa

Sat 1/17

11:30 am-2:39 pm

2 stops57h 09m

$623

PortlandRome

PWM - FCO

PWMFCO

Portland

Tue 1/20

2:31 pm-8:30 am

1 stop11h 59m

Rome Fiumicino

Thu 1/29

7:05 am-6:50 pm

2 stops17h 45m

$623

PortlandMilan

PWM - MXP

PWMMXP

Portland

Sat 1/10

2:35 pm-10:35 am

2 stops14h 00m

Milan Malpensa

Sat 1/17

11:05 am-10:27 pm

1 stop17h 22m

$634

PortlandMilan

PWM - MXP

PWMMXP

Portland

Sat 1/10

2:35 pm-5:25 pm

2 stops20h 50m

Milan Malpensa

Sat 1/17

12:00 pm-11:59 pm

1 stop17h 59m

$634

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 27 results
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Best time to book a flight from Portland to Italy

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

What is the cheapest month to book a flight from Portland, Maine to Italy?

Currently, May is the cheapest month in which you can book a flight from Portland, Maine to Italy (average of $270). Flying from Portland, Maine to Italy in June is currently the most expensive (average of $471). 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.

What is the cheapest time of day to fly from PWM to IT?

Find hourly flight availability from Portland to Italy. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.

When flying from Portland, Maine to Italy, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 19% versus a flight in the morning.

Reviews of airlines servicing Italy

Get insights into the airlines that provide service to Italy. 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 Italy. Reviews last updated December 12, 2025.
Read through reviews of airlines operating flights from Portland to Italy, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,095 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,095 reviews
United Airlines
7.4
Good
9,095 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
American Airlines
7.2
Good
11,050 reviews
United Airlines
7.4
Good
9,095 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

Related info for your journey

Find useful and relevant information for your journey from Portland 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 Portland to Italy?

    Portland (PWM), located 2.9 mi from the city center, is the airport you fly out of when you book flights from Portland to Italy.

  • How long is the flight from Portland, Maine to Italy?

    Delta, Scandinavian Airlines, and United Airlines can get you from Portland, Maine to Italy in just under 20h 15m. Your travel time can differ by up to 15h 35m. There are 3749 mi between Portland, Maine and Italy. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Portland, Maine to Italy?

    While some choose either Portland - Rome Fiumicino or Portland - Milan Linate, Portland - Florence Peretola is the most popular route from Portland, Maine to Italy.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland 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 Portland, Maine to Italy?

    Currently, May is the cheapest month in which you can book a flight from Portland, Maine to Italy (average of $270). Flying from Portland, Maine to Italy in June is currently the most expensive (average of $471). 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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Top airline flying from Portland to Italy

Discover the top airline that operate flights from Portland to Italy. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$629Average$1,103FlexibilityNo cancel feeOn-time69%

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