$140 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 12/31. 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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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$470
Saint Thomas Island
Saint Thomas Islandnonstop$679
Kingston
Kingston2 stops$1,018
Simpson Bay
Simpson Bay1 stop$350
Port of Spain
Port of Spain1 stop$578
Bridgetown
Bridgetown1 stop$428
St. John's
St. John'snonstop$365
Santo Domingo
Santo Domingononstop$470
Saint Thomas Island
Saint Thomas Islandnonstop$679
Kingston
Kingston2 stops$1,018
Simpson Bay
Simpson Bay1 stop$350
Port of Spain
Port of Spain1 stop$578
Bridgetown
Bridgetown1 stop$428
St. John's
St. John'snonstop$365

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, Dec 31 - Sun, Jan 4
Caribbean Airlines Logo
12:50 pm - 1:45 pm
EIS
-
SJU
0h 55mnonstop
Caribbean Airlines Logo
3:15 pm - 4:05 pm
SJU
-
EIS
0h 50mnonstop
$255Caribbean Airlines
Wed, Dec 31 - Sat, Jan 3
Multiple Airlines Logo
12:50 pm - 1:45 pm
EIS
-
SJU
0h 55mnonstop
Multiple Airlines Logo
2:35 pm - 3:15 pm
SJU
-
EIS
0h 40mnonstop
$257Multiple Airlines
Thu, Jan 22 - Thu, Jan 29
interCaribbean Airways Logo
8:55 am - 9:35 am
EIS
-
SJU
0h 40mnonstop
interCaribbean Airways Logo
10:15 am - 10:55 am
SJU
-
EIS
0h 40mnonstop
$275interCaribbean Airways
Fri, Mar 6 - Tue, Mar 10
interCaribbean Airways Logo
4:00 pm - 4:40 pm
EIS
-
SJU
0h 40mnonstop
interCaribbean Airways Logo
2:35 pm - 3:15 pm
SJU
-
EIS
0h 40mnonstop
$276interCaribbean Airways
Wed, Dec 31 - Sun, Jan 4
interCaribbean Airways Logo
8:55 am - 9:35 am
EIS
-
SJU
0h 40mnonstop
interCaribbean Airways Logo
10:15 am - 10:55 am
SJU
-
EIS
0h 40mnonstop
$280interCaribbean Airways
Tue, Jan 20 - Sun, Jan 25
interCaribbean Airways Logo
12:10 pm - 12:50 pm
EIS
-
SJU
0h 40mnonstop
interCaribbean Airways Logo
10:15 am - 10:55 am
SJU
-
EIS
0h 40mnonstop
$285interCaribbean Airways
Fri, Jan 16 - Mon, Jan 19
interCaribbean Airways Logo
4:00 pm - 4:40 pm
EIS
-
SJU
0h 40mnonstop
interCaribbean Airways Logo
10:15 am - 10:55 am
SJU
-
EIS
0h 40mnonstop
$315interCaribbean Airways
Fri, Dec 26 - Wed, Dec 31
interCaribbean Airways Logo
12:10 pm - 12:50 pm
EIS
-
SJU
0h 40mnonstop
interCaribbean Airways Logo
10:15 am - 10:55 am
SJU
-
EIS
0h 40mnonstop
$320interCaribbean Airways
Tue, Mar 31 - Tue, Apr 7
Winair Logo
11:35 am - 2:00 pm
EIS
-
SXM
2h 25m1 stop
Winair Logo
6:50 pm - 7:35 pm
SXM
-
EIS
0h 45mnonstop
$350Winair
Wed, Dec 24 - Sun, Jan 25
Winair Logo
7:15 am - 9:05 am
EIS
-
SXM
1h 50m1 stop
Winair Logo
10:20 am - 11:05 am
SXM
-
EIS
0h 45mnonstop
$351Winair
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 72 hours was to San Juan, at $274 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 72 hours was $274.

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 $459, 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 January, when tickets cost $155 (return) on average. On the other hand, the most expensive months are March and July, when the average cost of round-trip tickets is $312 and $301 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 Sunday is the most expensive. Flying from Caribbean Islands back to Road Town, the best deals are generally found on Tuesday, with Monday being the most expensive.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$140
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Road Town to San Juan

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.

  • 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 $275 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 at night, which is peak travel time and where the average cost of a ticket is $1,020.

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 $159 one-way - $388 round-trip; San Juan $171 one-way - $280 round-trip; Simpson Bay $212 one-way - $405 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.
8.0
Caribbean AirlinesOverall score based on 208 reviews
8.4Crew
7.8Comfort
6.6Entertainment
6.8Food
8.0Boarding
Airline reviews

Overall, it was good. There was no food or entertainment, which is why I put poor (it wasn't an issue though).

8.0 ExcellentLorrian, Dec 2025
GND - BGI
Read more Caribbean Airlines reviews

Overall, it was good. There was no food or entertainment, which is why I put poor (it wasn't an issue though).

Nothing, they could have made some accommodation for an awful experience. Me and my family were not informed properly we we separated. They took me off the original flight i booked. I booked our flight at one price and called me and told me they were not honoring my rate and they charged me double of what I paid. Me and my family don’t want to ever use your services again.

This flight was great. The plane took off and arrived at the destination an hour early. The crew was pleasant. The food and entertainment options are minimal but adequate for a 1-hour flight. They passed out water and quickly supplied me with a fresh magazine since the previous one had the crossword section filled out.

Better movie and tv selections. Also, the overnight flight to Trinidad from Toronto, the staff were not very attentive. I did not see them for at least half the fight. They were behind their curtain a lot of the time, and they did not check on us before landing to make sure all landing requirements were met.

Little space for luggage and the flight was delayed by an hour.

The flight was delayed over a hour and that was over 15 hours in advance not good

At check in I had to pay for my seat that I already paid for on purchasing my ticket. The flight was over an hour late and the plane smelt gross.

just a child who screamed and threw tantrums the entire flight

Excellent experience this was my first time booking with Kayak.

Flight ended up being longer than anticipated because we had to reroute to the Bahamas. So a hour and half flight turned into 5 hours. 0/10.

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

Road Town (EIS)