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Caribbean Islands

$165+ Cheap flights from South Dakota 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — SJU
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
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Cheap flight deals from South Dakota to Caribbean Islands

Cheapest flights from South Dakota to Caribbean Islands
Explore the most affordable flight options available from South Dakota to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.

This American Airlines deal was found by Cheapflights users on 2/3. 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 3/95:21 pm
FSD
-
SJU
2 stops14h 39m
American Airlines
Thu 3/121:30 am
SJU
-
FSD
1 stop12h 11m
American Airlines
Deal found 2/3$319
This Delta deal was found by Cheapflights users on 2/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:25 am
FSD
-
SJU
2 stops12h 48m
Delta
Sat 5/91:55 pm
SJU
-
FSD
2 stops10h 02m
Delta
Deal found 2/4$338
This United Airlines deal was found by Cheapflights users on 2/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
FSD
-
SJU
1 stop10h 38m
United Airlines
Fri 5/81:00 am
SJU
-
FSD
2 stops12h 44m
United Airlines
Deal found 2/4$343
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Mon 2/236:14 pm
FSD
-
STT
1 stop20h 20m
Multiple Airlines
Tue 3/33:36 pm
STT
-
FSD
2 stops47h 45m
Multiple Airlines
Deal found 2/3$355
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/26:45 am
FSD
-
SJU
2 stops13h 04m
American Airlines
Wed 3/119:50 am
SJU
-
FSD
2 stops10h 20m
American Airlines
Deal found 2/2$357
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Mon 3/26:09 pm
FSD
-
STT
1 stop20h 25m
Multiple Airlines
Thu 3/55:40 pm
STT
-
FSD
2 stops26h 07m
Multiple Airlines
Deal found 2/2$364
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Mon 3/26:09 pm
FSD
-
STT
1 stop20h 25m
Multiple Airlines
Wed 3/43:36 pm
STT
-
FSD
1 stop27h 12m
Multiple Airlines
Deal found 2/2$369
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Mon 3/26:09 pm
FSD
-
STT
1 stop20h 25m
Multiple Airlines
Sun 3/82:36 pm
STT
-
FSD
2 stops30h 23m
Multiple Airlines
Deal found 2/2$376
This United Airlines deal was found by Cheapflights users on 2/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:40 am
FSD
-
SJU
2 stops12h 42m
United Airlines
Thu 2/267:40 am
SJU
-
FSD
2 stops14h 59m
United Airlines
Deal found 2/1$392
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Mon 2/97:01 pm
FSD
-
SJU
2 stops18h 05m
Multiple Airlines
Thu 2/124:36 pm
SJU
-
FSD
1 stop26h 48m
Multiple Airlines
Deal found 2/3$398
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 5/16:11 pm
FSD
-
SJU
1 stop19h 20m
Multiple Airlines
Sat 5/97:53 pm
SJU
-
FSD
2 stops46h 28m
Multiple Airlines
Deal found 2/1$400
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Mon 2/236:14 pm
FSD
-
SJU
1 stop19h 17m
Multiple Airlines
Mon 3/25:25 pm
SJU
-
FSD
1 stop19h 47m
Multiple Airlines
Deal found 2/2$405

Find flight deals from South Dakota to Caribbean Islands

Keep the following information in mind while searching for South Dakota to Caribbean Islands flight deals. Data was last updated February 4, 2026.

Round-trip from

$319
(American Airlines)

One-way from

$165
(Kiwi.com)

Popular in

November

Cheapest in

February

Average price

$371
From South Dakota to Caribbean Islands
Search Deals
One-way flight from South Dakota to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($94 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from South Dakota 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 February 4, 2026.
Use the filters below to find and compare flights from South Dakota to Caribbean Islands that are best for you.

Fly from

South Dakota

Fly to

Caribbean Islands

Route

Depart

Return

Price

Sioux FallsSan Juan

FSD - SJU

FSDSJU

Sioux Falls Joe Foss Field

Mon 3/9

5:21 pm-9:00 am

2 stops14h 39m

San Juan Luis Munoz Marin Intl

Thu 3/12

1:30 am-12:41 pm

1 stop12h 11m

$319

Sioux FallsSan Juan

FSD - SJU

FSDSJU

Sioux Falls Joe Foss Field

Sat 5/2

9:25 am-11:13 pm

2 stops12h 48m

San Juan Luis Munoz Marin Intl

Sat 5/9

1:55 pm-10:57 pm

2 stops10h 02m

$338

Sioux FallsSan Juan

FSD - SJU

FSDSJU

Sioux Falls Joe Foss Field

Mon 2/23

7:40 am-10:22 pm

2 stops12h 42m

San Juan Luis Munoz Marin Intl

Thu 2/26

7:40 am-8:39 pm

2 stops14h 59m

$392

Sioux FallsSan Juan

FSD - SJU

FSDSJU

Sioux Falls Joe Foss Field

Sat 5/2

7:39 pm-2:20 pm

1 stop17h 41m

San Juan Luis Munoz Marin Intl

Sat 5/9

11:59 pm-12:56 pm

1 stop13h 57m

$398

Sioux FallsSan Juan

FSD - SJU

FSDSJU

Sioux Falls Joe Foss Field

Fri 5/1

6:11 pm-2:31 pm

1 stop19h 20m

San Juan Luis Munoz Marin Intl

Sat 5/9

7:53 pm-5:21 pm

2 stops46h 28m

$400

Sioux FallsSan Juan

FSD - SJU

FSDSJU

Sioux Falls Joe Foss Field

Mon 2/23

6:14 pm-3:31 pm

1 stop19h 17m

San Juan Luis Munoz Marin Intl

Mon 3/2

5:25 pm-11:12 am

1 stop19h 47m

$405

Sioux FallsSaint Thomas Island

FSD - STT

FSDSTT

Sioux Falls Joe Foss Field

Mon 3/2

6:09 pm-4:34 pm

1 stop20h 25m

Saint Thomas Island Cyril E King

Thu 3/5

5:40 pm-5:21 pm

1 stop25h 41m

$405

Sioux FallsSan Juan

FSD - SJU

FSDSJU

Sioux Falls Joe Foss Field

Fri 5/1

5:10 am-1:14 pm

1 stop7h 04m

San Juan Luis Munoz Marin Intl

Sat 5/9

4:15 pm-10:57 pm

1 stop7h 42m

$406

Sioux FallsSan Juan

FSD - SJU

FSDSJU

Sioux Falls Joe Foss Field

Wed 5/27

12:20 pm-10:51 pm

1 stop9h 31m

San Juan Luis Munoz Marin Intl

Fri 6/5

12:59 am-11:50 am

1 stop11h 51m

$422

Sioux FallsSaint Thomas Island

FSD - STT

FSDSTT

Sioux Falls Joe Foss Field

Mon 3/2

6:09 pm-4:34 pm

1 stop20h 25m

Saint Thomas Island Cyril E King

Tue 3/10

2:36 pm-1:46 pm

2 stops24h 10m

$426

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

Showing 1-10 of 44 results
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Best time to book a flight from South Dakota to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from South Dakota 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 South Dakota to Caribbean Islands

What is the cheapest month to book a flight from South Dakota to Caribbean Islands?

Currently, February is the cheapest month in which you can book a flight from South Dakota to Caribbean Islands (average of $236). Flying from South Dakota to Caribbean Islands in October is currently the most expensive (average of $390). 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.

Related info for your journey

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

  • How long is the flight from South Dakota to Caribbean Islands?

    For as low as $392, American Airlines can have you in Caribbean Islands from South Dakota in 12h 42m. There are 2488 mi between South Dakota and Caribbean Islands. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

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

  • How can I find direct flights from South Dakota to Caribbean Islands?

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

  • Can I find deals for business class flights from South Dakota to Caribbean Islands?

    Yes. Cheapflights offers flight deals from South Dakota 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 South Dakota to Caribbean Islands?

    Currently, February is the cheapest month in which you can book a flight from South Dakota to Caribbean Islands (average of $236). Flying from South Dakota to Caribbean Islands in October is currently the most expensive (average of $390). 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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Alternative routes for South Dakota to Caribbean Islands

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Top 3 airlines flying from South Dakota to Caribbean Islands

Discover the top 3 airlines that operate flights from South Dakota 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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$258Average$705FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$275Average$637FlexibilityNo cancel feeOn-time71%
DeltaCheapest$308Average$766FlexibilityNo cancel feeOn-timeN/A

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