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$235+ Cheap flights from Springfield, IL (SPI) to Caribbean

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
SPI — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/11. 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 12/236:14 pmSPI - SJU
2 stops15h 25mAmerican Airlines
Fri 1/236:00 amSJU - SPI
1 stop10h 18mAmerican Airlines
Deal found 12/11$417
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/296:14 pmSPI - SJU
1 stop8h 46mAmerican Airlines
Tue 1/136:00 amSJU - SPI
2 stops18h 14mAmerican Airlines
Deal found 12/10$502
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/316:00 amSPI - SJU
2 stops25h 35mAmerican Airlines
Tue 1/66:00 amSJU - SPI
2 stops18h 14mAmerican Airlines
Deal found 12/10$530
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/296:14 pmSPI - SJU
1 stop8h 46mAmerican Airlines
Sat 1/106:00 amSJU - SPI
2 stops18h 14mAmerican Airlines
Deal found 12/10$547
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/296:14 pmSPI - SJU
1 stop8h 46mAmerican Airlines
Mon 1/127:12 pmSJU - SPI
2 stops21h 43mAmerican Airlines
Deal found 12/10$600
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/296:14 pmSPI - SJU
1 stop8h 46mAmerican Airlines
Fri 1/94:28 pmSJU - SPI
1 stop7h 46mAmerican Airlines
Deal found 12/10$657
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/266:00 amSPI - STT
1 stop6h 59mAmerican Airlines
Tue 12/303:39 pmSTT - SPI
1 stop9h 56mAmerican Airlines
Deal found 12/11$1,481

Find flight deals from Springfield to Caribbean

Keep the following information in mind while searching for Springfield to Caribbean flight deals. Data was last updated December 12, 2025.

Round-trip from

$235
(American Airlines)
From Springfield Capital to Caribbean
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 December 12, 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

SPI - SJU

SPISJU

Springfield Capital

Thu 1/1

6:00 am-11:34 pm

2 stops15h 34m

San Juan Luis Munoz Marin Intl

Thu 1/29

6:00 am-2:18 pm

1 stop10h 18m

$235

SpringfieldSan Juan

SPI - SJU

SPISJU

Springfield Capital

Thu 1/1

6:00 am-11:34 pm

2 stops15h 34m

San Juan Luis Munoz Marin Intl

Wed 1/14

11:38 am-10:14 pm

2 stops12h 36m

$235

SpringfieldSan Juan

SPI - SJU

SPISJU

Springfield Capital

Tue 12/23

6:14 pm-11:39 am

2 stops15h 25m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:00 am-2:18 pm

1 stop10h 18m

$417

SpringfieldSan Juan

SPI - SJU

SPISJU

Springfield Capital

Thu 1/1

6:00 am-11:34 pm

2 stops15h 34m

San Juan Luis Munoz Marin Intl

Wed 1/7

6:00 am-10:14 pm

1 stop18h 14m

$450

SpringfieldSaint Thomas Island

SPI - STT

SPISTT

Springfield Capital

Fri 12/26

6:00 am-2:59 pm

1 stop6h 59m

Saint Thomas Island Cyril E King

Tue 12/30

3:39 pm-11:35 pm

1 stop9h 56m

$1,481

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

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, Illinois to Caribbean?

Currently, May is the cheapest month in which you can book a flight from Springfield, Illinois to Caribbean (average of $140). Flying from Springfield, Illinois to Caribbean in June is currently the most expensive (average of $249). 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

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 December 12, 2025.
Read reviews from past customers who have flown American Airlines from Springfield to Caribbean. 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.
American Airlines
7.2
Good
11,050 reviews

Food

6.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Boarding

7.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,050 reviews
American Airlines
7.2
Good
11,050 reviews

Food

6.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Boarding

7.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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?

    Springfield Capital (SPI), located 3.4 mi from the city center, is the airport you fly out of when you book flights from Springfield to Caribbean.

  • How long is the flight from Springfield, Illinois to Caribbean?

    American Airlines can get you from Springfield, Illinois to Caribbean in just under 15h 34m. Your travel time can differ by up to . The distance from Springfield, Illinois to Caribbean is about 2042 mi.

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

    When deciding which route to take from Springfield, Illinois to Caribbean consider Springfield Capital - San Juan Luis Munoz Marin Intl, Springfield Capital - Nassau Intl or Springfield Capital - Saint Thomas Island Cyril E King as they are the most popular.

  • 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, Illinois to Caribbean?

    Currently, May is the cheapest month in which you can book a flight from Springfield, Illinois to Caribbean (average of $140). Flying from Springfield, Illinois to Caribbean in June is currently the most expensive (average of $249). 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 airline flying from Springfield to Caribbean

Discover the top airline 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$225Average$548FlexibilityNo cancel feeOn-time71%

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