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$365+ 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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
SPI — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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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 September 11, 2025.

Round-trip from

$365
(American Airlines)
From Springfield Capital to Caribbean
Search Deals

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 September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/11. 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.
Mon 12/16:18 pmSPI - SJU
2 stops20h 47mAmerican Airlines
Wed 12/106:00 amSJU - SPI
2 stops16h 09mAmerican Airlines
Deal found 9/11$365
This American Airlines deal was found by Cheapflights users on 9/10. 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 12/246:14 pmSPI - SJU
2 stops19h 32mAmerican Airlines
Thu 1/110:26 amSJU - SPI
2 stops14h 59mAmerican Airlines
Deal found 9/10$825
This American Airlines deal was found by Cheapflights users on 9/11. 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 12/266:14 pmSPI - SJU
2 stops17h 31mAmerican Airlines
Tue 12/305:24 amSJU - SPI
2 stops14h 20mAmerican Airlines
Deal found 9/11$1,190

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 September 11, 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

Mon 12/1

6:18 pm-5:05 pm

2 stops20h 47m

San Juan Luis Munoz Marin Intl

Wed 12/10

6:00 am-8:09 pm

2 stops16h 09m

$365

SpringfieldSan Juan

SPI - SJU

SPISJU

Springfield Capital

Sun 3/1

6:39 pm-1:30 pm

2 stops16h 51m

San Juan Luis Munoz Marin Intl

Wed 3/4

12:45 pm-11:01 pm

2 stops12h 16m

$400

SpringfieldSan Juan

SPI - SJU

SPISJU

Springfield Capital

Thu 1/1

6:14 pm-5:04 am

1 stop8h 50m

San Juan Luis Munoz Marin Intl

Fri 1/9

7:15 am-11:08 pm

2 stops17h 53m

$495

SpringfieldSan Juan

SPI - SJU

SPISJU

Springfield Capital

Wed 12/24

6:14 pm-5:04 am

1 stop8h 50m

San Juan Luis Munoz Marin Intl

Thu 1/1

10:26 am-11:25 pm

2 stops14h 59m

$825

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

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, September is the cheapest month in which you can book a flight from Springfield, Illinois to Caribbean (average of $254). Flying from Springfield, Illinois to Caribbean 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

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 September 11, 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
10,000 reviews

Entertainment

6.9

Food

6.4

Overall

7.2

Comfort

7.2

Boarding

7.5

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
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Food

6.4

Overall

7.2

Comfort

7.2

Boarding

7.5

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 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 20h 47m. 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, September is the cheapest month in which you can book a flight from Springfield, Illinois to Caribbean (average of $254). Flying from Springfield, Illinois to Caribbean 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.

See more FAQs

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$225Average$477FlexibilityNo cancel feeOn-time71%

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