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Road Town

$861+ Cheap flights from Portland, ME (PWM) to Road Town (EIS)

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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EIS
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap flight deals from Portland to Road Town

Cheapest flights from Portland to Road Town
Explore the most affordable flight options available from Portland to Road Town. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.

This Travelocity deal was found by Cheapflights users on 1/27. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:00 am
PWM
-
EIS
2 stops29h 05m
Multiple Airlines
Mon 5/48:15 am
EIS
-
PWM
2 stops29h 08m
Multiple Airlines
Deal found 1/27$861
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Fri 3/136:17 am
PWM
-
EIS
2 stops14h 46m
American Airlines
Fri 3/208:48 am
EIS
-
PWM
2 stops14h 46m
American Airlines
Deal found 1/27$960
This United Airlines deal was found by Cheapflights users on 1/26. 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 3/316:00 am
PWM
-
EIS
2 stops10h 15m
United Airlines
Wed 4/13:00 pm
EIS
-
PWM
2 stops54h 40m
United Airlines
Deal found 1/26$1,170

Find 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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$861
(Travelocity)
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.
Search Deals
From Portland to Road Town Beef Island
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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 January 27, 2026.
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

Wed 4/29

6:00 am-11:05 am

2 stops29h 05m

Road Town Beef Island

Mon 5/4

8:15 am-1:23 pm

2 stops29h 08m

$861

PortlandRoad Town

PWM - EIS

PWMEIS

Portland

Fri 3/13

6:17 am-9:03 pm

2 stops14h 46m

Road Town Beef Island

Fri 3/20

8:48 am-11:34 pm

2 stops14h 46m

$960

PortlandRoad Town

PWM - EIS

PWMEIS

Portland

Tue 3/31

6:00 am-4:15 pm

2 stops10h 15m

Road Town Beef Island

Wed 4/1

3:00 pm-9:40 pm

2 stops54h 40m

$1,170

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

  • Most accurate provider: When it comes to deals on Portland, Maine-Road Town flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Road Town flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, June is the cheapest month in which you can book a flight from Portland, Maine to Road Town (average of $617). Flying from Portland, Maine to Road Town in September is currently the most expensive (average of $727). 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.

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

    A quick flight from Portland, Maine to Road Town can take about 10h 15m. American Airlines provides one of the quickest options available for as low as $1,170. There are 1772 mi between Portland, Maine and Road Town. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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, June is the cheapest month in which you can book a flight from Portland, Maine to Road Town (average of $617). Flying from Portland, Maine to Road Town in September is currently the most expensive (average of $727). 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.

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