PDX - EIS

$433 Find Cheap Flights from Portland to Road Town - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Road Town departing on 10/23. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Road Town

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Road Town, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Road Town, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$894
American Airlines
Thu 8/6Thu 8/13
PDX - EIS • 2 stops
Cheapest one-way
$433
American Airlines
Fri 10/23
PDX - EIS • 2 stops
Top airlines
Cheapest • from $894 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Portland and Road Town. You'll need at least 1 connection.
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We hope you love your trip to Road Town!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Portland to Road Town (PDX-EIS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Road Town that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Portland to Road Town

Thu, Aug 6 - Thu, Aug 13
American Airlines Logo
10:59 pm - 4:25 pm
PDX
-
EIS
14h 26m
2 stops
American Airlines Logo
5:05 pm - 10:54 am
EIS
-
PDX
20h 49m
2 stops
$894American Airlines
Fri, Oct 30 - Sun, Nov 15
American Airlines Logo
11:58 pm - 4:25 pm
PDX
-
EIS
13h 27m
2 stops
American Airlines Logo
5:45 pm - 12:36 pm
EIS
-
PDX
22h 51m
2 stops
$920American Airlines
Sat, Aug 8 - Sat, Aug 15
American Airlines Logo
3:00 pm - 2:06 pm
PDX
-
EIS
20h 06m
2 stops
American Airlines Logo
5:05 pm - 10:54 am
EIS
-
PDX
20h 49m
2 stops
$935American Airlines
Fri, Oct 30 - Sun, Nov 15
American Airlines Logo
11:58 pm - 4:25 pm
PDX
-
EIS
13h 27m
2 stops
American Airlines Logo
5:45 pm - 12:36 pm
EIS
-
PDX
22h 51m
2 stops
$940American Airlines
Thu, Aug 6 - Thu, Aug 13
United Airlines Logo
12:50 pm - 7:00 pm
PDX
-
EIS
27h 10m
3 stops
United Airlines Logo
9:45 am - 9:59 pm
EIS
-
PDX
15h 14m
2 stops
$995United Airlines
Sat, Aug 8 - Sat, Aug 15
United Airlines Logo
12:50 pm - 3:38 pm
PDX
-
EIS
47h 48m
3 stops
United Airlines Logo
9:20 am - 10:59 pm
EIS
-
PDX
40h 39m
2 stops
$1,018United Airlines
Fri, Oct 30 - Sun, Nov 15
United Airlines Logo
1:15 pm - 7:15 pm
PDX
-
EIS
27h 00m
3 stops
United Airlines Logo
10:33 am - 9:21 am
EIS
-
PDX
26h 48m
2 stops
$1,127United Airlines
Fri, Oct 30 - Sun, Nov 15
American Airlines Logo
11:58 pm - 4:25 pm
PDX
-
EIS
13h 27m
2 stops
American Airlines Logo
2:41 pm - 11:51 pm
EIS
-
PDX
13h 10m
1 stop
$1,333American Airlines
Fri, Oct 30 - Sun, Nov 15
American Airlines Logo
11:58 pm - 4:25 pm
PDX
-
EIS
13h 27m
2 stops
American Airlines Logo
2:41 pm - 11:51 pm
EIS
-
PDX
13h 10m
1 stop
$1,338American Airlines
Booking Insights

KAYAK's insights & trends for Portland to Road Town flights

Get data-powered insights and trends into flights from Portland to Road Town to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Portland to Road Town?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 5 days.

In the past 5 days, the cheapest round-trip tickets from Portland to Road Town were found on American Airlines ($894) and United Airlines ($995).

Good to know

Cheapest flight$433
Flight from Portland to Road Town

When to book flights from Portland to Road Town

Are your dates flexible? Find out the best times to travel from Portland to Road Town based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Portland to Road Town

  • What is the cheapest flight from Portland to Road Town?

    In the last 5 days, the lowest price for a flight from Portland to Road Town was $433 for a one-way ticket and $894 for a round-trip.

  • Do I need a passport to fly between Portland and Road Town?

    Yes

  • Which aircraft models fly most regularly from Portland to Road Town?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Portland to Road Town?

    oneworld is the only airline alliance operating flights between Portland and Road Town.

  • How does KAYAK find such low prices on flights from Portland to Road Town?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Portland to Road Town.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to Road Town?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Road Town from Portland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Portland to Road Town?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Road Town with an airline and back to Portland with another airline. Booking your flights between Portland and EIS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Portland to Road Town?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Road Town from Portland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Portland to Road Town

 
See real verified KAYAK customer reviews for airlines flying from Portland to Road Town. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Portland to Road Town? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11779 reviews
7.2Comfort
7.9Crew
7.5Boarding
6.8Entertainment
6.4Food
Airline reviews

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

2.0 MediocreMatthew, May 2026
PDX - ORD
Read more American Airlines reviews

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

Horrible. Got delayed many hours because their pilot wasn't trained for night landing at the airport and a rain delay made it a night landing. We have to wait hours for a qualified crew. They give us 12 dollar meal vouchers but most everything in the airport was closed and definitely more expensive than the vouchers.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

As smooth as you can expect. Some issues with boarding because the previous plane took forever to deplane but overall, a good experience.

DFW-LHR Toilets not kept clean Too cramped. Aisles so narrow crew were constantly banging into people on the aisle seats. Even then, the carts used are reduced width. Other than that it was a decent flight on both legs

Excellent customer service at check in at Austin flight to DFW and excellent customer service from Karren in terminal B at DFW.

The flight itself was fine, but between the man in front of me putting his chair back, and the gentleman next to me who took up 50% of my seat, my back and neck are destroyed from the flight. I’m hoping for a better outcome flying back.

Flight boarded without pilots. Sat on plane for 3 hrs. after over an hour late boarding. Plane never took off. Had to deplane near midnight. Line for rebooking was 3 hours + long. I had to leave.

We were told there would be no food/beverage service due to turbulence. There was very little turbulence on the 2+ hour flight. I was in First Class and thought they could have done a quick service after take off as they had a quite bit of time before we would be reaching the predicted turbulent area. They could have at least passed out a quick bag of pretzels.

Very disappointed with the crew and the lack of attention given to the passengers. On a 5 hour flight they never offered a snack. One time offered a beverage and didn’t pick up the used cups until the flight was on final approach. The two flight attendants in our section mentioned that they were best friends and compared their pre flight shoes. When paying for first/business class there is a level of service that should be expected. These two spent the majority of the flight in their seats playing on their phones and laughing with each other. Very frustrating!!!

Everything you need to know for your flight from Portland to Road Town

Information on your arrival and departure airports