$132 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 8/13. 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

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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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$465
Saint Thomas Island
Saint Thomas Islandnonstop$553
Kingston
Kingston2 stops$835
Simpson Bay
Simpson Baynonstop$360
Port of Spain
Port of Spain2 stops$553
Bridgetown
Bridgetown1 stop$445
Castries
Castries2 stops$674
St. John's
St. John'snonstop$365
Santo Domingo
Santo Domingononstop$465
Saint Thomas Island
Saint Thomas Islandnonstop$553
Kingston
Kingston2 stops$835
Simpson Bay
Simpson Baynonstop$360
Port of Spain
Port of Spain2 stops$553
Bridgetown
Bridgetown1 stop$445
Castries
Castries2 stops$674
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

Thu, Oct 16 - Fri, Dec 26
interCaribbean Airways Logo
4:00 pm - 4:40 pmEIS-SJU
0h 40mnonstop
interCaribbean Airways Logo
1:30 pm - 2:10 pmSJU-EIS
0h 40mnonstop
$254interCaribbean Airways
Find Deal
Mon, Dec 15 - Mon, Dec 15
interCaribbean Airways Logo
8:55 am - 9:35 amEIS-SJU
0h 40mnonstop
interCaribbean Airways Logo
1:30 pm - 2:10 pmSJU-EIS
0h 40mnonstop
$257interCaribbean Airways
Find Deal
Wed, Dec 3 - Wed, Dec 10
interCaribbean Airways Logo
12:10 pm - 12:50 pmEIS-SJU
0h 40mnonstop
interCaribbean Airways Logo
2:35 pm - 3:15 pmSJU-EIS
0h 40mnonstop
$264interCaribbean Airways
Find Deal
Thu, Sep 18 - Sun, Sep 21
Winair Logo
7:05 pm - 7:50 pmEIS-SXM
0h 45mnonstop
Winair Logo
10:20 am - 11:05 amSXM-EIS
0h 45mnonstop
$360Winair
Find Deal
Thu, Sep 18 - Sun, Sep 21
Winair Logo
7:05 pm - 7:50 pmEIS-SXM
0h 45mnonstop
Winair Logo
10:20 am - 11:05 amSXM-EIS
0h 45mnonstop
$361Winair
Find Deal
Fri, Oct 17 - Sun, Oct 19
Logo
1:15 pm - 1:55 pmEIS-SXM
0h 40mnonstop
Logo
10:20 am - 11:05 amSXM-EIS
0h 45mnonstop
$387
Find Deal
Thu, Sep 18 - Sun, Sep 21
Logo
11:50 am - 2:15 pmEIS-SXM
2h 25m1 stop
Logo
3:50 pm - 12:35 pmSXM-EIS
20h 45m1 stop
$410
Find Deal
Thu, Oct 16 - Fri, Dec 26
Caribbean Airlines Logo
4:50 pm - 12:15 pmEIS-SJU
19h 25m3 stops
Caribbean Airlines Logo
3:15 pm - 4:05 pmSJU-EIS
0h 50mnonstop
$500Caribbean Airlines
Find Deal
Sat, Oct 4 - Sun, Nov 30
Sunrise Airways Logo
1:05 pm - 3:25 pmEIS-SXM
2h 20m1 stop
Sunrise Airways Logo
10:45 am - 12:35 pmSXM-EIS
25h 50m3 stops
$587Sunrise Airways
Find Deal
Thu, Oct 16 - Sun, Oct 19
Sunrise Airways Logo
12:05 pm - 2:40 pmEIS-SXM
2h 35m1 stop
Sunrise Airways Logo
10:45 am - 12:35 pmSXM-EIS
25h 50m3 stops
$590Sunrise Airways
Find Deal
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 price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Road Town to Caribbean Islands.

The cheapest ticket to Caribbean Islands from Road Town found in the last 72 hours was to San Juan, at $109 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 $109.

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 $524, 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 $115 (return) on average. On the other hand, the most expensive months are March and April, when the average cost of round-trip tickets is $312 and $296 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 Wednesday 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 seasonFebruary
Cheapest flight$132
Best time to beat the crowds with an average 40% drop in price.
Most popular time to fly and prices are also 7% 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 at night, when round-trip flights cost $125 on average. Morning departures are around 2% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $674.

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 $266 one-way - $372 round-trip; San Juan $197 one-way - $274 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.
8.1
Caribbean AirlinesOverall score based on 166 reviews
7.9Comfort
8.4Crew
6.8Food
8.1Boarding
6.7Entertainment
Airline reviews

Flight time. The crew was the rudest, talked down to customers, ignored requests, acted like security guards, used forceful language like must and can't. Everything was on purchase, no entertainment, unless you could use your own phone. Poor customer service.

4.0 OkaySheldon, Jul 2025MIA - POS
Read more Caribbean Airlines reviews

Flight time. The crew was the rudest, talked down to customers, ignored requests, acted like security guards, used forceful language like must and can't. Everything was on purchase, no entertainment, unless you could use your own phone. Poor customer service.

Checking in, boarding, the food and crew were all excellent. It was my first time traveling on Caribbean Airlines and trust me it’s the only airline I’ll be flying on as of now as long as it’s going my way😁. The service was unbelievably good I don’t regret missing my flight on flair at all cause I wouldn’t have realized how great the service is on Caribbean Airlines

The flight could'nt be better ,the comfort ,the crew and everything was good.i will definitely fly with this sirline again.

I love my entire experience. What I love most, was the friendliness and helpfulness of the staff at check-in and that of the crew on the flight. Their Customer Service was paramount.

The flight crew was extremely hospitable, though there was a lot of turbulence, they made it a good experience. The only negative was the inflight experience for economy class. There wasn’t any, or at least non that I was aware of.

I liked the friendliness of the employees at the airport

I liked the extra leg room in Caribbean plus. Worth the extra money. The food could have been more balanced, there was no salad or veggies

The Flight itself was smooth and uneventful. The crew was polite and caring. I used the Lounge in Piarco and the service was STELLAR

Crew were quite friendly. Food was very poor considering the price of the ticket and the flight time. Could not charge my phone due to USB charger not working..

The food wasn’t good. Need better food. There wasn’t any entertainment.

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)

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