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Caribbean Islands

$115+ Cheap flights from Springfield (SGF) 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
SGF — SJU
Apr 7 — Apr 141
Tue 4/7
Tue 4/14
1 adult, Economy
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Cheap flight deals from Springfield to Caribbean Islands

Cheapest flights from Springfield to Caribbean Islands
Explore the most affordable flight options available from Springfield to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 8, 2026.

This United Airlines deal was found by Cheapflights users on 3/7. 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.
Tue 4/286:00 am
SGF
-
SJU
1 stop7h 44m
United Airlines
Tue 5/57:20 am
SJU
-
SGF
2 stops15h 42m
United Airlines
Deal found 3/7$252
This American Airlines deal was found by Cheapflights users on 3/2. 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.
Sat 4/256:24 pm
SGF
-
SJU
1 stop15h 24m
American Airlines
Thu 4/3011:59 pm
SJU
-
SGF
1 stop11h 25m
American Airlines
Deal found 3/2$258
This American Airlines deal was found by Cheapflights users on 3/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/257:08 am
SGF
-
SJU
1 stop14h 54m
American Airlines
Sat 5/211:59 pm
SJU
-
SGF
1 stop10h 25m
American Airlines
Deal found 3/4$278
This Delta deal was found by Cheapflights users on 3/6. 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.
Tue 4/283:59 pm
SGF
-
SJU
1 stop6h 14m
Delta
Tue 5/52:45 pm
SJU
-
SGF
1 stop7h 22m
Delta
Deal found 3/6$310
This American Airlines deal was found by Cheapflights users on 3/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:24 pm
SGF
-
SJU
1 stop15h 24m
American Airlines
Wed 4/153:34 pm
SJU
-
SGF
1 stop18h 50m
American Airlines
Deal found 3/4$321
This American Airlines deal was found by Cheapflights users on 3/6. 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 4/288:26 am
SGF
-
SJU
1 stop13h 36m
American Airlines
Tue 5/55:45 am
SJU
-
SGF
2 stops12h 50m
American Airlines
Deal found 3/6$326
This American Airlines deal was found by Cheapflights users on 3/3. 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.
Tue 4/144:49 pm
SGF
-
MBJ
2 stops19h 02m
American Airlines
Tue 4/2112:56 pm
MBJ
-
SGF
2 stops20h 28m
American Airlines
Deal found 3/3$337
This American Airlines deal was found by Cheapflights users on 3/5. 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 5/276:48 pm
SGF
-
MBJ
2 stops16h 57m
American Airlines
Mon 6/15:17 pm
MBJ
-
SGF
2 stops19h 00m
American Airlines
Deal found 3/5$342
This American Airlines deal was found by Cheapflights users on 3/3. 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.
Tue 5/56:00 pm
SGF
-
SJU
2 stops14h 13m
American Airlines
Tue 5/127:25 am
SJU
-
SGF
1 stop10h 37m
American Airlines
Deal found 3/3$343
This American Airlines deal was found by Cheapflights users on 3/3. 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.
Sat 5/165:47 pm
SGF
-
MBJ
2 stops17h 37m
American Airlines
Fri 5/2212:31 pm
MBJ
-
SGF
2 stops23h 46m
American Airlines
Deal found 3/3$357
This American Airlines deal was found by Cheapflights users on 3/3. 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.
Tue 5/126:00 pm
SGF
-
MBJ
2 stops17h 24m
American Airlines
Sat 5/232:08 pm
MBJ
-
SGF
2 stops22h 44m
American Airlines
Deal found 3/3$362
This American Airlines deal was found by Cheapflights users on 3/3. 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.
Thu 5/147:34 pm
SGF
-
MBJ
2 stops15h 50m
American Airlines
Sat 5/232:08 pm
MBJ
-
SGF
2 stops20h 49m
American Airlines
Deal found 3/3$367

Find flight deals from Springfield to Caribbean Islands

Keep the following information in mind while searching for Springfield to Caribbean Islands flight deals. Data was last updated March 8, 2026.

Round-trip from

$252
(United Airlines)

One-way from

$115
(United Airlines)

Popular in

July

Cheapest in

September

Average price

$510
From Springfield-Branson to Caribbean Islands
Search Deals
One-way flight from Springfield-Branson to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 33% potential increase in price ($285 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Springfield 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 March 8, 2026.
Use the filters below to find and compare flights from Springfield to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

SpringfieldSan Juan

SGF - SJU

SGFSJU

Springfield-Branson

Tue 4/28

6:00 am-2:44 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

Tue 5/5

7:20 am-10:02 pm

2 stops15h 42m

$252

SpringfieldSan Juan

SGF - SJU

SGFSJU

Springfield-Branson

Tue 4/28

3:59 pm-11:13 pm

1 stop6h 14m

San Juan Luis Munoz Marin Intl

Tue 5/5

2:45 pm-9:07 pm

1 stop7h 22m

$310

SpringfieldMontego Bay

SGF - MBJ

SGFMBJ

Springfield-Branson

Wed 5/27

6:48 pm-11:45 am

2 stops16h 57m

Montego Bay Sangster Intl

Mon 6/1

5:17 pm-12:17 pm

2 stops19h 00m

$342

SpringfieldMontego Bay

SGF - MBJ

SGFMBJ

Springfield-Branson

Tue 4/14

6:00 am-3:10 pm

2 stops9h 10m

Montego Bay Sangster Intl

Sat 4/25

4:12 pm-10:48 am

2 stops18h 36m

$342

SpringfieldMontego Bay

SGF - MBJ

SGFMBJ

Springfield-Branson

Fri 4/17

6:00 am-12:50 pm

1 stop6h 50m

Montego Bay Sangster Intl

Fri 4/24

1:52 pm-10:48 am

1 stop20h 56m

$343

SpringfieldSan Juan

SGF - SJU

SGFSJU

Springfield-Branson

Sat 4/11

7:00 am-3:35 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Wed 4/15

11:43 am-8:46 pm

2 stops10h 03m

$346

SpringfieldSan Juan

SGF - SJU

SGFSJU

Springfield-Branson

Sat 4/25

6:00 am-8:38 pm

2 stops13h 38m

San Juan Luis Munoz Marin Intl

Thu 4/30

7:40 am-2:35 pm

1 stop7h 55m

$360

SpringfieldProvidenciales

SGF - PLS

SGFPLS

Springfield-Branson

Mon 5/11

6:24 pm-12:25 pm

2 stops17h 01m

Providenciales

Tue 5/19

3:23 pm-11:14 am

2 stops20h 51m

$368

SpringfieldSaint Thomas Island

SGF - STT

SGFSTT

Springfield-Branson

Tue 4/28

6:00 am-4:15 pm

2 stops9h 15m

Saint Thomas Island Cyril E King

Tue 5/5

5:05 pm-10:24 am

2 stops18h 19m

$372

SpringfieldSaint Thomas Island

SGF - STT

SGFSTT

Springfield-Branson

Fri 5/8

3:36 pm-11:35 am

2 stops18h 59m

Saint Thomas Island Cyril E King

Mon 5/11

5:05 pm-10:24 am

2 stops18h 19m

$372

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/4

Showing 1-10 of 48 resultsSorted by cheapest first
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5

Best time to book a flight from Springfield to Caribbean Islands

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

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

Currently, February is the cheapest month in which you can book a flight from Springfield to Caribbean Islands (average of $128). Flying from Springfield to Caribbean Islands in June is currently the most expensive (average of $452). 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 March 8, 2026.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Springfield to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,269 reviews

Food

7.2

Comfort

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,269 reviews
Delta
7.9
Good
8,269 reviews

Food

7.2

Comfort

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,405 reviews
Delta
7.9
Good
8,269 reviews

Food

7.2

Comfort

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.1
Good
11,397 reviews
Delta
7.9
Good
8,269 reviews

Food

7.2

Comfort

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

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

    Springfield-Branson (SGF), located 5.3 mi from the city center, is the airport you fly out of when you book flights from Springfield to Caribbean Islands.

  • How long is the flight from Springfield to Caribbean Islands?

    Airlines like United Airlines, Delta, and American Airlines fly from Springfield to Caribbean Islands in about 6h 14m. The time it takes to get you to your destination can typically vary by up to 10h 43m. Springfield and Caribbean Islands are separated by a distance of 2103 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Springfield to Caribbean Islands one-way?

    $118 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 American Airlines and Delta, with prices starting from $161 and $282, respectively.

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

    The most popular route from Springfield to Caribbean Islands is Springfield-Branson - San Juan Luis Munoz Marin Intl. You may also consider Springfield-Branson - Oranjestad Reina Beatrix or Springfield-Branson - Punta Cana.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Springfield 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 Springfield to Caribbean Islands?

    Currently, February is the cheapest month in which you can book a flight from Springfield to Caribbean Islands (average of $128). Flying from Springfield to Caribbean Islands in June is currently the most expensive (average of $452). 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 Springfield to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Springfield to Caribbean Islands

Discover the top 3 airlines that operate flights from Springfield 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 March 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$128Average$599FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$257Average$627FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$266Average$603FlexibilityNo cancel feeOn-time71%

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