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Caribbean

$260+ Cheap flights from Springfield (SGF) to Caribbean

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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
SGF — SJU
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Find flight deals from Springfield to Caribbean

Cheapest flights from Springfield to Caribbean
Explore the most affordable flight options available from Springfield to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.

This American Airlines deal was found by Cheapflights users on 10/13. 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.
Sun 12/74:23 pmSGF - SJU
2 stops15h 46mAmerican Airlines
Sat 12/138:18 amSJU - SGF
1 stop16h 15mAmerican Airlines
Deal found 10/13$295
This American Airlines deal was found by Cheapflights users on 10/14. 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 12/35:35 pmSGF - SJU
2 stops14h 34mAmerican Airlines
Tue 12/98:20 amSJU - SGF
1 stop14h 34mAmerican Airlines
Deal found 10/14$298
This American Airlines deal was found by Cheapflights users on 10/13. 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 12/66:34 pmSGF - SJU
2 stops13h 35mAmerican Airlines
Sat 12/133:12 pmSJU - SGF
1 stop9h 21mAmerican Airlines
Deal found 10/13$301
This Delta deal was found by Cheapflights users on 10/14. 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 10/286:00 amSGF - PUJ
1 stop6h 24mDelta
Fri 10/313:56 pmPUJ - SGF
1 stop7h 13mDelta
Deal found 10/14$335
This American Airlines deal was found by Cheapflights users on 10/13. 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 12/66:34 pmSGF - SJU
2 stops13h 35mAmerican Airlines
Fri 12/125:10 pmSJU - SGF
2 stops17h 36mAmerican Airlines
Deal found 10/13$340
This United Airlines deal was found by Cheapflights users on 10/14. 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 10/283:20 pmSGF - PUJ
2 stops19h 39mUnited Airlines
Fri 10/311:55 pmPUJ - SGF
1 stop9h 18mUnited Airlines
Deal found 10/14$340
This United Airlines deal was found by Cheapflights users on 10/13. 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 12/811:31 amSGF - SJU
1 stop7h 29mUnited Airlines
Tue 12/167:45 amSJU - SGF
1 stop8h 19mUnited Airlines
Deal found 10/13$366
This American Airlines deal was found by Cheapflights users on 10/14. 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 11/286:34 pmSGF - PUJ
1 stop15h 06mAmerican Airlines
Fri 12/52:29 pmPUJ - SGF
1 stop9h 05mAmerican Airlines
Deal found 10/14$379
This American Airlines deal was found by Cheapflights users on 10/13. 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.
Sun 12/76:34 pmSGF - SJU
2 stops13h 35mAmerican Airlines
Mon 12/156:00 amSJU - SGF
2 stops18h 22mAmerican Airlines
Deal found 10/13$382
This American Airlines deal was found by Cheapflights users on 10/13. 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 12/54:08 pmSGF - SJU
2 stops20h 07mAmerican Airlines
Thu 12/1111:00 amSJU - SGF
2 stops13h 22mAmerican Airlines
Deal found 10/13$385
This United Airlines deal was found by Cheapflights users on 10/12. 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 10/2811:26 amSGF - SJU
2 stops11h 10mUnited Airlines
Sat 11/12:46 pmSJU - SGF
1 stop8h 00mUnited Airlines
Deal found 10/12$399
This American Airlines deal was found by Cheapflights users on 10/14. 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.
Sun 12/147:03 amSGF - PUJ
1 stop7h 26mAmerican Airlines
Thu 12/183:51 pmPUJ - SGF
1 stop10h 05mAmerican Airlines
Deal found 10/14$405

Cheap flight deals from Springfield to Caribbean

Keep the following information in mind while searching for Springfield to Caribbean flight deals. Data was last updated October 14, 2025.

Round-trip from

$235
(American Airlines)

Popular in

July

Cheapest in

April

Average price

$407
From Springfield-Branson to Caribbean
Search Deals
Highest demand for flights based on searches. 34% potential increase in price ($273 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($34 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 Springfield to Caribbean 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 14, 2025.
Use the filters below to find and compare flights from Springfield to Caribbean that are best for you.

Fly from

Springfield

Fly to

Caribbean

Route

Depart

Return

Price

SpringfieldSan Juan

SGF - SJU

SGFSJU

Springfield-Branson

Tue 1/27

5:39 pm-12:32 pm

2 stops16h 53m

San Juan Luis Munoz Marin Intl

Fri 1/30

8:20 am-4:14 pm

2 stops9h 54m

$268

SpringfieldSan Juan

SGF - SJU

SGFSJU

Springfield-Branson

Tue 12/9

10:16 am-10:09 am

2 stops21h 53m

San Juan Luis Munoz Marin Intl

Wed 12/17

3:45 pm-10:22 pm

1 stop8h 37m

$295

SpringfieldSan Juan

SGF - SJU

SGFSJU

Springfield-Branson

Sun 2/1

8:50 am-9:26 pm

1 stop10h 36m

San Juan Luis Munoz Marin Intl

Mon 2/9

2:05 am-2:38 pm

2 stops14h 33m

$325

SpringfieldSan Juan

SGF - SJU

SGFSJU

Springfield-Branson

Wed 12/3

5:35 pm-10:09 am

2 stops14h 34m

San Juan Luis Munoz Marin Intl

Tue 12/9

6:00 am-5:05 pm

2 stops13h 05m

$331

SpringfieldPunta Cana

SGF - PUJ

SGFPUJ

Springfield-Branson

Tue 10/28

6:00 am-1:24 pm

1 stop6h 24m

Punta Cana

Fri 10/31

3:56 pm-10:09 pm

1 stop7h 13m

$335

SpringfieldPunta Cana

SGF - PUJ

SGFPUJ

Springfield-Branson

Tue 10/28

3:20 pm-11:59 am

2 stops19h 39m

Punta Cana

Fri 10/31

4:20 pm-10:51 am

2 stops19h 31m

$340

SpringfieldSan Juan

SGF - SJU

SGFSJU

Springfield-Branson

Sat 12/6

6:34 pm-10:09 am

2 stops13h 35m

San Juan Luis Munoz Marin Intl

Sat 12/13

6:00 am-10:33 pm

2 stops18h 33m

$340

SpringfieldSan Juan

SGF - SJU

SGFSJU

Springfield-Branson

Sat 12/6

6:34 pm-10:09 am

2 stops13h 35m

San Juan Luis Munoz Marin Intl

Fri 12/12

5:10 pm-8:46 am

2 stops17h 36m

$340

SpringfieldSan Juan

SGF - SJU

SGFSJU

Springfield-Branson

Wed 12/10

6:16 pm-10:09 am

2 stops13h 53m

San Juan Luis Munoz Marin Intl

Tue 12/16

4:50 pm-9:46 am

2 stops18h 56m

$340

SpringfieldSan Juan

SGF - SJU

SGFSJU

Springfield-Branson

Sat 12/6

10:28 am-10:09 am

2 stops21h 41m

San Juan Luis Munoz Marin Intl

Tue 12/16

4:50 pm-9:46 am

2 stops18h 56m

$340

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

Showing 1-10 of 30 results
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Best time to book a flight from Springfield to Caribbean

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

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

Currently, September is the cheapest month in which you can book a flight from Springfield to Caribbean (average of $198). Flying from Springfield to Caribbean in July is currently the most expensive (average of $472). 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 SGF to CB?

Find hourly flight availability from Springfield to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 14, 2025.

When flying from Springfield to Caribbean, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 15% versus a flight in the morning.

What is the cheapest day to fly from Springfield to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Springfield to Caribbean. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Springfield to Caribbean flight should consider departing on Thursday afternoons when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated October 14, 2025.
Read through reviews of airlines operating flights from Springfield to Caribbean, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,975 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
8.0
Very good
7,975 reviews
Delta
8.0
Very good
7,975 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,976 reviews
Delta
8.0
Very good
7,975 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,042 reviews
Delta
8.0
Very good
7,975 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

Related info for your journey

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

    Most people fly from Springfield-Branson (SGF) if they book a flight from Springfield to Caribbean. Springfield-Branson is conveniently located just 5.3 mi from Springfield’s city center.

  • How long is the flight from Springfield to Caribbean?

    There are many flights that can get you from Springfield to Caribbean in 6h 24m. Fly via American Airlines, United Airlines, or Delta to get the fastest option. The distance from Springfield to Caribbean is about 1987 mi. This flight may include one or multiple stops.

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

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

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Springfield to Caribbean 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?

    Currently, September is the cheapest month in which you can book a flight from Springfield to Caribbean (average of $198). Flying from Springfield to Caribbean in July is currently the most expensive (average of $472). 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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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

Discover the top 3 airlines that operate flights from Springfield to Caribbean. 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 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$246Average$613FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$252Average$587FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$265Average$649FlexibilityNo cancel feeOn-time71%

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