$131 Find Cheap Flights from Road Town to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Road Town to Caribbean Islands departing on 9/26. 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 Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Road Town to Caribbean Islands, 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 Road Town to Caribbean Islands, as well as popular online travel agencies
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Booking Insights
Flight Deals

Cheap Flights from Road Town to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Santo Domingo
Santo Domingononstop$487
Kingston
Kingston1 stop$480
Simpson Bay
Simpson Baynonstop$338
Port of Spain
Port of Spain2 stops$682
Bridgetown
Bridgetown1 stop$453
Castries
Castries2 stops$632
St. John's
St. John'snonstop$382
Santo Domingo
Santo Domingononstop$487
Kingston
Kingston1 stop$480
Simpson Bay
Simpson Baynonstop$338
Port of Spain
Port of Spain2 stops$682
Bridgetown
Bridgetown1 stop$453
Castries
Castries2 stops$632
St. John's
St. John'snonstop$382

Book Cheap Road Town to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Road Town to Caribbean Islands 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 Road Town to Caribbean Islands

Wed, Jul 1 - Wed, Jul 8
interCaribbean Airways Logo
4:00 pm - 4:40 pm
EIS
-
SJU
0h 40mnonstop
interCaribbean Airways Logo
1:25 pm - 2:05 pm
SJU
-
EIS
0h 40mnonstop
$309interCaribbean Airways
Sat, Jul 4 - Sat, Jul 11
interCaribbean Airways Logo
9:00 am - 9:40 am
EIS
-
SJU
0h 40mnonstop
interCaribbean Airways Logo
5:30 pm - 6:10 pm
SJU
-
EIS
0h 40mnonstop
$310interCaribbean Airways
Sat, Jun 27 - Tue, Jun 30
interCaribbean Airways Logo
4:00 pm - 4:40 pm
EIS
-
SJU
0h 40mnonstop
interCaribbean Airways Logo
5:30 pm - 6:10 pm
SJU
-
EIS
0h 40mnonstop
$315interCaribbean Airways
Tue, Jul 21 - Tue, Jul 28
interCaribbean Airways Logo
11:35 am - 12:15 pm
EIS
-
SJU
0h 40mnonstop
interCaribbean Airways Logo
5:30 pm - 6:10 pm
SJU
-
EIS
0h 40mnonstop
$330interCaribbean Airways
Tue, Sep 1 - Wed, Sep 16
interCaribbean Airways Logo
4:00 pm - 4:40 pm
EIS
-
SJU
0h 40mnonstop
interCaribbean Airways Logo
5:30 pm - 6:10 pm
SJU
-
EIS
0h 40mnonstop
$336interCaribbean Airways
Thu, Jul 9 - Thu, Jul 16
Winair Logo
7:55 pm - 8:40 pm
EIS
-
SXM
0h 45mnonstop
Winair Logo
10:20 am - 11:05 am
SXM
-
EIS
0h 45mnonstop
$338Winair
Sat, Jul 4 - Mon, Jul 6
Multiple Airlines Logo
1:45 pm - 2:25 pm
EIS
-
SXM
0h 40mnonstop
Multiple Airlines Logo
10:20 am - 11:05 am
SXM
-
EIS
0h 45mnonstop
$343Multiple Airlines
Fri, Jul 3 - Mon, Jul 6
Winair Logo
11:35 am - 2:05 pm
EIS
-
SXM
2h 30m
1 stop
Winair Logo
10:20 am - 11:05 am
SXM
-
EIS
0h 45mnonstop
$348Winair
Sun, Jul 5 - Sun, Jul 12
Winair Logo
11:35 am - 2:05 pm
EIS
-
SXM
2h 30m
1 stop
Winair Logo
10:20 am - 11:05 am
SXM
-
EIS
0h 45mnonstop
$386Winair
Sun, Jul 5 - Sun, Jul 12
Winair Logo
8:00 pm - 8:50 pm
EIS
-
SXM
0h 50mnonstop
Winair Logo
10:20 am - 11:05 am
SXM
-
EIS
0h 45mnonstop
$387Winair
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Road Town found in the last 5 days was to San Juan, at $299 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 $299.

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

The average price for all round-trip flights from Road Town to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

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 8% 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 $302.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $481, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Road Town to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Road Town to Caribbean Islands is August, when tickets cost $143 (return) on average. On the other hand, the most expensive months are November and February, when the average cost of round-trip tickets is $374 and $365 respectively.

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

The average price of all round-trip flights from Road Town to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

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 Tuesday being the most expensive.

Good to know

Low seasonFebruary
Cheapest flight$131
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Road Town to Simpson Bay

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: St. John's $313 one-way - $371 round-trip; San Juan $172 one-way - $302 round-trip

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

 
See real verified KAYAK customer reviews for airlines flying from Road Town to Caribbean Islands. 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 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
8.5Boarding
7.5Food
9.5Crew
8.0Comfort
7.5Entertainment
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
SBH - SXM
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.

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports