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Caribbean Islands

$175+ Cheap flights from Santa Rosa (STS) 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
STS — SJU
Nov 1 — Nov 81
Sat 11/1
Sat 11/8
1 adult, Economy
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Cheap flight deals from Santa Rosa to Caribbean Islands

Keep the following information in mind while searching for Santa Rosa to Caribbean Islands flight deals. Data was last updated October 2, 2025.

Round-trip from

$337
(American Airlines)

One-way from

$175
(American Airlines)

Popular in

December

Cheapest in

May

Average price

$457
From Santa Rosa Sonoma County to Caribbean Islands
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One-way flight from Santa Rosa Sonoma County to Caribbean Islands
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Highest demand for flights based on searches. 7% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Santa Rosa to Caribbean Islands

Cheapest flights from Santa Rosa to Caribbean Islands
Explore the most affordable flight options available from Santa Rosa to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 2, 2025.

This American Airlines deal was found by Cheapflights users on 9/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/24:23 pmSTS - SJU
2 stops13h 44mAmerican Airlines
Fri 12/123:58 pmSJU - STS
2 stops24h 29mAmerican Airlines
Deal found 9/30$465
This American Airlines deal was found by Cheapflights users on 9/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/71:18 pmSTS - STI
2 stops27h 33mAmerican Airlines
Mon 11/174:35 pmSTI - STS
2 stops23h 32mAmerican Airlines
Deal found 9/30$526
This American Airlines deal was found by Cheapflights users on 9/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:00 amSTS - SJU
2 stops23h 07mAmerican Airlines
Fri 12/123:58 pmSJU - STS
2 stops24h 29mAmerican Airlines
Deal found 9/30$540
This American Airlines deal was found by Cheapflights users on 9/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/44:26 pmSTS - SJU
2 stops20h 37mAmerican Airlines
Fri 12/123:58 pmSJU - STS
2 stops24h 29mAmerican Airlines
Deal found 9/30$541
This American Airlines deal was found by Cheapflights users on 9/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/71:18 pmSTS - STI
2 stops27h 33mAmerican Airlines
Wed 11/194:35 pmSTI - STS
2 stops24h 13mAmerican Airlines
Deal found 9/30$546
This American Airlines deal was found by Cheapflights users on 9/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/71:18 pmSTS - STI
2 stops27h 33mAmerican Airlines
Sun 11/234:35 pmSTI - STS
2 stops23h 31mAmerican Airlines
Deal found 9/30$582
This American Airlines deal was found by Cheapflights users on 9/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/21:18 pmSTS - SJU
2 stops16h 49mAmerican Airlines
Sat 12/133:12 pmSJU - STS
2 stops25h 15mAmerican Airlines
Deal found 9/30$593
This American Airlines deal was found by Cheapflights users on 9/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:00 amSTS - SJU
2 stops23h 07mAmerican Airlines
Mon 12/86:25 amSJU - STS
2 stops21h 27mAmerican Airlines
Deal found 9/30$615
This American Airlines deal was found by Cheapflights users on 9/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/44:26 pmSTS - SJU
2 stops21h 26mAmerican Airlines
Thu 12/118:18 amSJU - STS
2 stops19h 34mAmerican Airlines
Deal found 9/30$616
This American Airlines deal was found by Cheapflights users on 9/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/14:23 pmSTS - SJU
2 stops18h 37mAmerican Airlines
Wed 12/103:45 pmSJU - STS
2 stops24h 42mAmerican Airlines
Deal found 9/30$621
This American Airlines deal was found by Cheapflights users on 9/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/127:45 amSTS - STI
2 stops27h 48mAmerican Airlines
Mon 11/174:35 pmSTI - STS
2 stops23h 32mAmerican Airlines
Deal found 9/30$625
This American Airlines deal was found by Cheapflights users on 9/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1012:37 pmSTS - AUA
2 stops24h 13mAmerican Airlines
Thu 11/135:55 pmAUA - STS
2 stops22h 53mAmerican Airlines
Deal found 9/29$626

Cheapflights Fare Finder

 
Customize your flight search to find flights from Santa Rosa 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 2, 2025.
Use the filters below to find and compare flights from Santa Rosa to Caribbean Islands that are best for you.

Fly from

Santa Rosa

Fly to

Caribbean Islands

Route

Depart

Return

Price

Santa RosaSan Juan

STS - SJU

STSSJU

Santa Rosa Sonoma County

Sun 3/1

12:49 pm-2:43 pm

2 stops21h 54m

San Juan Luis Munoz Marin Intl

Wed 3/11

6:20 am-10:35 pm

2 stops19h 15m

$412

Santa RosaSan Juan

STS - SJU

STSSJU

Santa Rosa Sonoma County

Tue 3/3

12:49 pm-1:15 pm

2 stops20h 26m

San Juan Luis Munoz Marin Intl

Wed 3/4

4:15 pm-12:14 pm

2 stops23h 59m

$465

Santa RosaSan Juan

STS - SJU

STSSJU

Santa Rosa Sonoma County

Tue 12/2

4:23 pm-10:07 am

2 stops13h 44m

San Juan Luis Munoz Marin Intl

Wed 12/10

3:45 pm-12:27 pm

2 stops24h 42m

$465

Santa RosaSantiago de los Caballeros

STS - STI

STSSTI

Santa Rosa Sonoma County

Thu 11/13

1:18 pm-8:51 pm

2 stops27h 33m

Santiago de los Caballeros

Tue 11/18

7:00 am-12:07 pm

2 stops33h 07m

$526

Santa RosaSantiago de los Caballeros

STS - STI

STSSTI

Santa Rosa Sonoma County

Fri 11/7

1:18 pm-8:51 pm

2 stops27h 33m

Santiago de los Caballeros

Thu 11/20

4:35 pm-12:48 pm

2 stops24h 13m

$526

Santa RosaSantiago de los Caballeros

STS - STI

STSSTI

Santa Rosa Sonoma County

Tue 11/11

1:18 pm-3:33 pm

2 stops22h 15m

Santiago de los Caballeros

Tue 11/18

7:00 am-12:07 pm

2 stops33h 07m

$526

Santa RosaSantiago de los Caballeros

STS - STI

STSSTI

Santa Rosa Sonoma County

Thu 11/13

1:18 pm-8:51 pm

2 stops27h 33m

Santiago de los Caballeros

Thu 11/20

4:35 pm-12:48 pm

2 stops24h 13m

$526

Santa RosaSantiago de los Caballeros

STS - STI

STSSTI

Santa Rosa Sonoma County

Mon 11/10

4:23 pm-3:33 pm

2 stops19h 10m

Santiago de los Caballeros

Thu 11/20

4:35 pm-12:48 pm

2 stops24h 13m

$526

Santa RosaSantiago de los Caballeros

STS - STI

STSSTI

Santa Rosa Sonoma County

Mon 11/10

12:37 pm-3:33 pm

2 stops22h 56m

Santiago de los Caballeros

Mon 11/17

4:35 pm-12:07 pm

2 stops23h 32m

$526

Santa RosaSantiago de los Caballeros

STS - STI

STSSTI

Santa Rosa Sonoma County

Mon 3/30

4:12 pm-8:03 pm

2 stops24h 51m

Santiago de los Caballeros

Thu 4/2

7:00 am-12:19 pm

2 stops32h 19m

$526

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/2

Showing 1-10 of 36 results
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Best time to book a flight from Santa Rosa to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Santa Rosa 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 Santa Rosa to Caribbean Islands

What is the cheapest month to book a flight from Santa Rosa to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Santa Rosa to Caribbean Islands (average of $254). Flying from Santa Rosa to Caribbean Islands in June is currently the most expensive (average of $339). 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.

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 2, 2025.
Read reviews from past customers who have flown American Airlines from Santa Rosa to Caribbean Islands. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,033 reviews

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Food

6.4

Overall

7.2

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,033 reviews
American Airlines
7.2
Good
11,033 reviews

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Food

6.4

Overall

7.2

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

Related info for your journey

Find useful and relevant information for your journey from Santa Rosa 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 Santa Rosa to Caribbean Islands?

    If you book a flight to Caribbean Islands from Santa Rosa, you will be flying from Sonoma County, which is the city’s only airport. Santa Rosa Sonoma County (STS) is located 7.2 mi from the center of Santa Rosa.

  • How long is the flight from Santa Rosa to Caribbean Islands?

    For as low as $412, American Airlines can have you in Caribbean Islands from Santa Rosa in 21h 54m. There are 3652 mi between Santa Rosa and Caribbean Islands.

  • What are the most popular routes from Santa Rosa to Caribbean Islands?

    While some choose either Santa Rosa Sonoma County - Havana Jose Marti Intl or Santa Rosa Sonoma County - Nassau Intl, Santa Rosa Sonoma County - San Juan Luis Munoz Marin Intl is the most popular route from Santa Rosa to Caribbean Islands.

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

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

  • How can I find direct flights from Santa Rosa to Caribbean Islands?

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

  • Can I find deals for business class flights from Santa Rosa to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Santa Rosa 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 Santa Rosa to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from Santa Rosa to Caribbean Islands (average of $254). Flying from Santa Rosa to Caribbean Islands in June is currently the most expensive (average of $339). 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.

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Alternative routes for Santa Rosa to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Santa Rosa to Caribbean Islands

Discover the top airline that operate flights from Santa Rosa 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 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$560Average$872FlexibilityNo cancel feeOn-time71%

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