$125 Find Cheap Flights from Road Town to Caribbean Islands - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Road Town to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
San Juan
0h 40mNonstop
from $307per person
Simpson Bay
0h 40mNonstop
from $383per person
Booking Insights

KAYAK's insights & trends for Road Town to Caribbean Islands flights

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

What is the cheapest Road Town to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from Road Town found in the last 5 days was to San Juan, at $301 round-trip. The most popular route is from Road Town (EIS) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 5 days was $301.

What is the cheapest time of day to fly to Caribbean Islands?

The cheapest time of day to fly to Caribbean Islands is generally in the evening, when round-trip flights cost $280 on average. Morning departures are around 10% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $307.

Can I save money by flying with a layover from Road Town to Caribbean Islands?

No, with an average price for the route of $602, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Road Town to Caribbean Islands?

The cheapest month for flights from Road Town to Caribbean Islands is November, when tickets cost $387 (return) on average. On the other hand, the most expensive months are May and September, when the average cost of round-trip tickets is $466 and $466 respectively.

What’s the cheapest day of the week to fly from Road Town to Caribbean Islands?

For Road Town to Caribbean Islands, Tuesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Caribbean Islands back to Road Town, the best deals are generally found on Friday, with Monday being the most expensive.

Good to know

Low season

February
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 1% increase in price.

FAQs - booking Caribbean Islands flights

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

    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 Road Town to Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Road Town to Caribbean Islands 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 Road Town to Caribbean Islands?

    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 from Road Town to Caribbean Islands with an airline and back with another airline.

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

    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 from Road Town to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from Road Town to the following destinations at these prices or less: San Juan $211 one-way - $319 round-trip; Simpson Bay $195 one-way - $469 round-trip

Reviews of the top airlines flying from Road Town to Caribbean Islands

 
Need help choosing which airline to fly with from Road Town to Caribbean Islands? 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.
8.5
WinairOverall score based on 4 reviews
9.5Crew
7.5Entertainment
7.5Food
8.0Comfort
8.5Boarding
Airline reviews

windsor had major problems and their flights were canceled and delayed. we got lucky and they were able to put us on another plane 1 hour late. luckily we had a long enough layover and didn’t miss our connecting flights.

6.0 GoodAnonymous, May 2026
Read more Winair reviews

windsor had major problems and their flights were canceled and delayed. we got lucky and they were able to put us on another plane 1 hour late. luckily we had a long enough layover and didn’t miss our connecting flights.

InterCaribbean seems to always be late. I do not recommend it if you have connecting flights with other airlines. The rates are the same as other regional carriers, but their aircraft are not very comfortable and are often quite hot.

Flew St Vincent to Barbados on an ATR-40 (?), seating about 60 passengers. Pretty tight in there. Flt. attendant was very friendly. Short flight - up & down in 40 minutes.

No food, no entertainment - half-hour flight (up & down) Smallest plane I’ve ever been on - maybe 60 passenger capacity?

I've had bad flights with InterCaribbean before (cancellations, no gate agents, etc.), but this one went perfectly smoothly!

Long delay. No AC on the flight from Barbados to St. Lucia.

Did not get to travel, you canceled my flight and left me stranded for the hole day, it's another day and I can't get to my destination. I will not recommend any one to this away, bad service

Delay flight more than 8hours waiting and poor customer service!

Plane was extremely small so mind the size of your carry on

Other than lack of snacks, everything else went very well.

They don’t keep you updated on the flight status very well. It was late but nothing said

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