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Caribbean Islands

$151+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
EIS — SJU
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Booking.com deal was found by Cheapflights users on 12/17. 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.
Sun 12/287:15 amEIS - SXM
1 stop1h 50mWinair
Wed 12/3110:20 amSXM - EIS
Nonstop0h 45mWinair
Deal found 12/17$359
This Winair deal was found by Cheapflights users on 12/17. 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 Winair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/267:50 pmEIS - SXM
Nonstop0h 45mWinair
Tue 12/304:15 pmSXM - EIS
1 stop2h 25mWinair
Deal found 12/17$366
This Mytrip deal was found by Cheapflights users on 12/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1811:35 amEIS - SXM
1 stop2h 25mWinair
Thu 3/55:00 pmSXM - EIS
1 stop25h 55mWinair
Deal found 12/17$372
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Sun 12/287:15 amEIS - SXM
1 stop1h 50mMultiple Airlines
Wed 12/319:35 amSXM - EIS
2 stops25h 20mMultiple Airlines
Deal found 12/17$488
This Expedia deal was found by Cheapflights users on 12/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/182:55 pmEIS - SXM
2 stops17h 45mMultiple Airlines
Thu 3/55:00 pmSXM - EIS
1 stop2h 25mMultiple Airlines
Deal found 12/17$518
This FlightHub deal was found by Cheapflights users on 12/17. 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.
Fri 12/2611:55 amEIS - SXM
1 stop2h 25mMultiple Airlines
Tue 12/306:45 pmSXM - EIS
2 stops24h 00mMultiple Airlines
Deal found 12/17$886

Find 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 December 18, 2025.

Round-trip from

$276
(Kiwi.com)

One-way from

$151
(Mytrip)

Popular in

March

Cheapest in

January

Average price

$286
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. 7% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 18, 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

Thu 1/1

8:55 am-9:35 am

Nonstop0h 40m

San Juan Luis Munoz Marin Intl

Sat 1/10

2:35 pm-3:15 pm

Nonstop0h 40m

$276

Road TownSan Juan

EIS - SJU

EISSJU

Road Town Beef Island

Sat 1/31

8:55 am-9:35 am

Nonstop0h 40m

San Juan Luis Munoz Marin Intl

Sat 2/7

5:40 pm-6:20 pm

Nonstop0h 40m

$280

Road TownSan Juan

EIS - SJU

EISSJU

Road Town Beef Island

Sat 2/7

8:55 am-9:35 am

Nonstop0h 40m

San Juan Luis Munoz Marin Intl

Mon 2/9

1:30 pm-2:10 pm

Nonstop0h 40m

$315

Road TownSan Juan

EIS - SJU

EISSJU

Road Town Beef Island

Fri 1/16

4:00 pm-4:40 pm

Nonstop0h 40m

San Juan Luis Munoz Marin Intl

Mon 1/19

5:40 pm-6:20 pm

Nonstop0h 40m

$315

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Mon 1/12

11:35 am-9:20 am

1 stop21h 45m

Simpson Bay Princess Juliana

Thu 1/15

10:20 am-11:05 am

Nonstop0h 45m

$356

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Wed 3/18

11:35 am-9:20 am

1 stop21h 45m

Simpson Bay Princess Juliana

Wed 3/25

5:15 pm-7:05 pm

1 stop1h 50m

$357

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Sun 12/28

7:15 am-9:05 am

1 stop1h 50m

Simpson Bay Princess Juliana

Wed 12/31

5:15 pm-7:05 pm

1 stop1h 50m

$359

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Thu 1/29

7:55 pm-8:45 pm

Nonstop0h 50m

Simpson Bay Princess Juliana

Thu 2/5

10:20 am-11:05 am

Nonstop0h 45m

$366

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Mon 4/27

11:35 am-2:00 pm

1 stop2h 25m

Simpson Bay Princess Juliana

Fri 5/1

10:20 am-11:10 am

Nonstop0h 50m

$366

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Fri 3/27

11:35 am-2:00 pm

1 stop2h 25m

Simpson Bay Princess Juliana

Mon 3/30

10:20 am-11:05 am

Nonstop0h 45m

$366

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 25 results
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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 $263). 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 December 18, 2025.

It’s optimal to fly from Road Town to Caribbean Islands in the morning. By choosing this option you can save up to 35% on the cost of your flight, compared to a flight in the evening.

Weekly flight availability from Road Town to Caribbean Islands

Explore weekly flight availability from Road Town to Caribbean Islands. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 18, 2025.

The most flights from EIS to zzEPX are scheduled on a Monday (12 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).

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 December 18, 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
209 reviews

Comfort

7.8

Boarding

8.0

Food

6.8

Overall

8.0

Entertainment

6.6

Crew

8.4

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
209 reviews
Caribbean Airlines
8.0
Very good
209 reviews

Comfort

7.8

Boarding

8.0

Food

6.8

Overall

8.0

Entertainment

6.6

Crew

8.4

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc
interCaribbean Airways
5.4
Fair
25 reviews
Caribbean Airlines
8.0
Very good
209 reviews

Comfort

7.8

Boarding

8.0

Food

6.8

Overall

8.0

Entertainment

6.6

Crew

8.4

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 $276, 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 cheapest airlines to fly from Road Town to Caribbean Islands one-way?

    $112 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Silver Airways and Caribbean Airlines, with prices starting from $120 and $135, respectively.

  • 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: JetBlue (87%), Cape Air (86%), Caribbean Airlines (85%).

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

    The cheapest flight price from Road Town to Caribbean Islands is $157. On average you can expect to pay $458. 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 $263). 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

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Caribbean AirlinesCheapest$110Average$263FlexibilityNo cancel feeOn-timeN/A
Silver AirwaysCheapest$189Average$275FlexibilityNo cancel feeOn-timeN/A
interCaribbean AirwaysCheapest$194Average$388FlexibilityNo cancel feeOn-timeN/A
WinairCheapest$712Average$793FlexibilityNo cancel feeOn-timeN/A

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