HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$145+ Cheap flights from Road Town (EIS) to Caribbean Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
EIS — SJU
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Road Town to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Find flight deals from Road Town to Caribbean Islands

Cheapest flights from Road Town to Caribbean Islands
Explore the most affordable flight options available from Road Town to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/288:55 amEIS - SJU
Nonstop0h 40minterCaribbean Airways
Sun 11/305:40 pmSJU - EIS
Nonstop0h 40minterCaribbean Airways
Deal found 10/28$280
This Booking.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/228:55 amEIS - SJU
Nonstop0h 40minterCaribbean Airways
Mon 11/245:40 pmSJU - EIS
Nonstop0h 40minterCaribbean Airways
Deal found 10/29$306
This interCaribbean Airways deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure interCaribbean Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/218:55 amEIS - SJU
Nonstop0h 40minterCaribbean Airways
Mon 11/245:40 pmSJU - EIS
Nonstop0h 40minterCaribbean Airways
Deal found 10/28$311
This interCaribbean Airways deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure interCaribbean Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/144:00 pmEIS - SJU
Nonstop0h 40minterCaribbean Airways
Wed 12/175:40 pmSJU - EIS
Nonstop0h 40minterCaribbean Airways
Deal found 10/29$315
This interCaribbean Airways deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure interCaribbean Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/712:10 pmEIS - SJU
Nonstop0h 40minterCaribbean Airways
Mon 11/105:40 pmSJU - EIS
Nonstop0h 40minterCaribbean Airways
Deal found 10/29$320
This interCaribbean Airways deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure interCaribbean Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/134:00 pmEIS - SJU
Nonstop0h 40minterCaribbean Airways
Sat 12/205:40 pmSJU - EIS
Nonstop0h 40minterCaribbean Airways
Deal found 10/29$330
This Booking.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2411:35 amEIS - SXM
1 stop21h 45mWinair
Tue 12/304:15 pmSXM - EIS
1 stop2h 25mWinair
Deal found 10/28$359
This CheapOair deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/147:15 amEIS - SXM
1 stop1h 50mWinair
Wed 12/175:00 pmSXM - EIS
1 stop25h 40mWinair
Deal found 10/30$366
This FlightHub deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/214:00 pmEIS - SJU
Nonstop0h 40minterCaribbean Airways
Fri 12/265:40 pmSJU - EIS
Nonstop0h 40minterCaribbean Airways
Deal found 10/28$380
This deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/144:00 pmEIS - SJU
Nonstop0h 40minterCaribbean Airways
Fri 11/2110:15 amSJU - EIS
Nonstop0h 40minterCaribbean Airways
Deal found 10/29$385
This CheapOair deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:10 amEIS - SXM
Nonstop0h 50mWinair
Tue 12/1610:20 amSXM - EIS
Nonstop0h 45mWinair
Deal found 10/28$386
This CheapOair deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/298:10 amEIS - SXM
Nonstop0h 50mWinair
Tue 12/210:20 amSXM - EIS
Nonstop0h 45mWinair
Deal found 10/30$396

Cheap flight deals from Road Town to Caribbean Islands

Keep the following information in mind while searching for Road Town to Caribbean Islands flight deals. Data was last updated October 30, 2025.

Round-trip from

$274
(Kiwi.com)

One-way from

$145
(Booking.com)

Popular in

March

Cheapest in

January

Average price

$289
From Road Town Beef Island to Caribbean Islands
Search Deals
One-way flight from Road Town Beef Island to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Road Town to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 30, 2025.
Use the filters below to find and compare flights from Road Town to Caribbean Islands that are best for you.

Fly from

Road Town

Fly to

Caribbean Islands

Route

Depart

Return

Price

Road TownSan Juan

EIS - SJU

EISSJU

Road Town Beef Island

Sat 11/22

8:55 am-9:35 am

Nonstop0h 40m

San Juan Luis Munoz Marin Intl

Mon 11/24

5:40 pm-6:20 pm

Nonstop0h 40m

$306

Road TownSan Juan

EIS - SJU

EISSJU

Road Town Beef Island

Fri 4/3

8:55 am-9:35 am

Nonstop0h 40m

San Juan Luis Munoz Marin Intl

Sat 4/4

5:40 pm-6:20 pm

Nonstop0h 40m

$310

Road TownSan Juan

EIS - SJU

EISSJU

Road Town Beef Island

Fri 11/21

8:55 am-9:35 am

Nonstop0h 40m

San Juan Luis Munoz Marin Intl

Mon 11/24

5:40 pm-6:20 pm

Nonstop0h 40m

$311

Road TownSan Juan

EIS - SJU

EISSJU

Road Town Beef Island

Sun 12/14

4:00 pm-4:40 pm

Nonstop0h 40m

San Juan Luis Munoz Marin Intl

Wed 12/17

5:40 pm-6:20 pm

Nonstop0h 40m

$315

Road TownSan Juan

EIS - SJU

EISSJU

Road Town Beef Island

Fri 11/28

8:55 am-9:35 am

Nonstop0h 40m

San Juan Luis Munoz Marin Intl

Sun 11/30

5:40 pm-6:20 pm

Nonstop0h 40m

$320

Road TownSan Juan

EIS - SJU

EISSJU

Road Town Beef Island

Fri 12/12

4:00 pm-4:40 pm

Nonstop0h 40m

San Juan Luis Munoz Marin Intl

Fri 12/19

10:15 am-10:55 am

Nonstop0h 40m

$325

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Wed 12/24

11:35 am-9:20 am

1 stop21h 45m

Simpson Bay Princess Juliana

Tue 12/30

4:15 pm-6:40 pm

1 stop2h 25m

$359

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Sat 11/29

11:35 am-2:00 pm

1 stop2h 25m

Simpson Bay Princess Juliana

Tue 12/2

10:20 am-11:05 am

Nonstop0h 45m

$366

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Fri 12/12

11:55 am-2:20 pm

1 stop2h 25m

Simpson Bay Princess Juliana

Tue 12/16

4:15 pm-6:40 pm

1 stop2h 25m

$366

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Sun 12/14

7:50 pm-8:40 pm

Nonstop0h 50m

Simpson Bay Princess Juliana

Wed 12/17

5:15 pm-7:05 pm

1 stop1h 50m

$366

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 25 results
1
2
3

Best time to book a flight from Road Town to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Road Town with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Road Town to Caribbean Islands

What is the cheapest month to book a flight from Road Town to Caribbean Islands?

Currently, June is the cheapest month in which you can book a flight from Road Town to Caribbean Islands (average of $90). Flying from Road Town to Caribbean Islands in April is currently the most expensive (average of $262). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from EIS to EPX?

Find hourly flight availability from Road Town to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

It’s optimal to fly from Road Town to Caribbean Islands in the evening. By choosing this option you can save up to 88% on the cost of your flight, compared to a flight at noon.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated October 30, 2025.
Read through reviews of airlines operating flights from Road Town to Caribbean Islands, such as Caribbean Airlines and interCaribbean Airways. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Caribbean Airlines
8.0
Very good
194 reviews

Crew

8.4

Boarding

8.1

Comfort

7.8

Entertainment

6.7

Food

6.8

Overall

8.0

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc
Caribbean Airlines
8.0
Very good
194 reviews
Caribbean Airlines
8.0
Very good
194 reviews

Crew

8.4

Boarding

8.1

Comfort

7.8

Entertainment

6.7

Food

6.8

Overall

8.0

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc
interCaribbean Airways
5.2
Fair
24 reviews
Caribbean Airlines
8.0
Very good
194 reviews

Crew

8.4

Boarding

8.1

Comfort

7.8

Entertainment

6.7

Food

6.8

Overall

8.0

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc

Related info for your journey

Find useful and relevant information for your journey from Road Town to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Road Town to Caribbean Islands?

    Most people fly from Road Town Beef Island (EIS) if they book a flight from Road Town to Caribbean Islands. Road Town Beef Island is conveniently located just 5.2 mi from Road Town’s city center.

  • How long is the flight from Road Town to Caribbean Islands?

    For as low as $306, interCaribbean Airways can have you in Caribbean Islands from Road Town in 40m. The distance from Road Town to Caribbean Islands is about 96 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most reliable airlines from Road Town to Caribbean Islands?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Road Town to Caribbean Islands on time: Caribbean Airlines (96%), United Airlines (82%), Cape Air (81%).

  • What are the cheapest flights from Road Town to Caribbean Islands?

    The cheapest flight price from Road Town to Caribbean Islands is $166. On average you can expect to pay $445. The most popular route, (Road Town Beef Island - San Juan Luis Munoz Marin Intl), can usually be booked for $1,529.

  • Can I find deals for flights from Road Town to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Road Town to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Road Town to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Road Town to Caribbean Islands.

  • Can I find deals for business class flights from Road Town to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Road Town to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Road Town to Caribbean Islands?

    Currently, June is the cheapest month in which you can book a flight from Road Town to Caribbean Islands (average of $90). Flying from Road Town to Caribbean Islands in April is currently the most expensive (average of $262). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 4 airlines flying from Road Town to Caribbean Islands

Discover the top 4 airlines that operate flights from Road Town to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$90Average$185FlexibilityNo cancel feeOn-time69%
Caribbean AirlinesCheapest$110Average$266FlexibilityNo cancel feeOn-timeN/A
interCaribbean AirwaysCheapest$166Average$387FlexibilityNo cancel feeOn-timeN/A
Silver AirwaysCheapest$189Average$265FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.