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Road Town

$395+ Cheap flights from Portland, ME (PWM) to Road Town (EIS)

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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EIS
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Find flight deals from Portland to Road Town

One-way flights from Portland to Road Town
Search for one-way flight options from Portland to Road Town. Find affordable one-way fares based on user searches. Data last updated October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/273:15 pmPWM - EIS
3 stops47h 00mMultiple Airlines
Deal found 10/27$395
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/266:18 pmPWM - EIS
3 stops39h 37mMultiple Airlines
Deal found 10/27$436
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/19:46 amPWM - EIS
3 stops55h 34mMultiple Airlines
Deal found 10/27$452
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/307:22 pmPWM - EIS
2 stops46h 08mUnited Airlines
Deal found 10/27$459
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/276:00 amPWM - EIS
2 stops11h 30mUnited Airlines
Deal found 10/27$461
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/282:36 pmPWM - EIS
3 stops50h 44mMultiple Airlines
Deal found 10/27$494
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/295:43 amPWM - EIS
2 stops10h 23mAmerican Airlines
Deal found 10/27$522
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/26:00 amPWM - EIS
3 stops57h 15mUnited Airlines
Deal found 10/27$576
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/296:18 pmPWM - EIS
3 stops39h 37mMultiple Airlines
Deal found 10/27$660

Cheap flight deals from Portland to Road Town

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Road Town (EIS). 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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars
Provider with most accurate pricing for Portland-Road Town Beef Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Road Town Beef Island flights.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Road Town 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 October 29, 2025.
Use the filters below to find and compare flights from Portland to Road Town that are best for you.

Fly from

Portland

Fly to

Road Town

Route

Depart

Return

Price

PortlandRoad Town

PWM - EIS

PWMEIS

Portland

Thu 11/27

3:15 pm-3:15 pm

3 stops47h 00m

$395

PortlandRoad Town

PWM - EIS

PWMEIS

Portland

Tue 12/2

6:00 am-6:30 pm

2 stops11h 30m

$436

PortlandRoad Town

PWM - EIS

PWMEIS

Portland

Wed 11/26

6:18 pm-10:55 am

3 stops39h 37m

$436

PortlandRoad Town

PWM - EIS

PWMEIS

Portland

Mon 12/1

9:46 am-6:20 pm

3 stops55h 34m

$452

PortlandRoad Town

PWM - EIS

PWMEIS

Portland

Sun 11/30

7:22 pm-6:30 pm

2 stops46h 08m

$459

PortlandRoad Town

PWM - EIS

PWMEIS

Portland

Fri 11/28

5:30 am-6:30 pm

2 stops12h 00m

$461

PortlandRoad Town

PWM - EIS

PWMEIS

Portland

Thu 11/27

6:00 am-6:30 pm

2 stops11h 30m

$461

PortlandRoad Town

PWM - EIS

PWMEIS

Portland

Fri 11/28

2:36 pm-6:20 pm

3 stops50h 44m

$494

PortlandRoad Town

PWM - EIS

PWMEIS

Portland

Sat 11/29

5:43 am-5:06 pm

2 stops10h 23m

$522

PortlandRoad Town

PWM - EIS

PWMEIS

Portland

Sat 11/29

6:18 pm-10:55 am

3 stops39h 37m

$660

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Compare providers for flights from Portland to Road Town

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 Portland to Road Town in October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 Portland, Maine-Road Town flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Portland, Maine-Road Town flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Portland, Maine-Road Town flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland, Maine-Road Town flights, Cheapflights users trust eDreams the most. eDreams 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 Portland, Maine-Road Town 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 Portland to Road Town

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

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

Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Road Town (average of $576). Flying from Portland, Maine to Road Town in December is currently the most expensive (average of $820). 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 Portland to Road Town. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

  • How can I find direct flights from Portland to Road Town?

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

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

    Yes. Cheapflights offers flight deals from Portland to Road Town 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 Road Town?

    Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Road Town (average of $576). Flying from Portland, Maine to Road Town in December is currently the most expensive (average of $820). 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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