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Caribbean Islands

$295+ Cheap flights from Springfield, IL (SPI) to Caribbean Islands

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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
SPI — SJU
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheap 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 October 28, 2025.

Round-trip from

$295
(American Airlines)
From Springfield Capital to Caribbean Islands
Search Deals

Find 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 October 28, 2025.

This American Airlines deal was found by Cheapflights users on 10/26. 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 stops19h 48mAmerican Airlines
Wed 12/108:20 amSJU - SPI
2 stops13h 49mAmerican Airlines
Deal found 10/26$365
This American Airlines deal was found by Cheapflights users on 10/27. 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
1 stop8h 46mAmerican Airlines
Fri 1/236:00 amSJU - SPI
1 stop10h 18mAmerican Airlines
Deal found 10/27$600
This American Airlines deal was found by Cheapflights users on 10/27. 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 12/246:00 amSPI - SJU
2 stops14h 05mAmerican Airlines
Thu 1/16:00 amSJU - SPI
1 stop13h 44mAmerican Airlines
Deal found 10/27$825

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 October 28, 2025.
Use the filters below to find and compare flights from Springfield to Caribbean Islands that are best for you.

Fly from

Springfield

Fly to

Caribbean Islands

Route

Depart

Return

Price

SpringfieldSan Juan

SPI - SJU

SPISJU

Springfield Capital

Sun 3/1

6:00 am-10:35 pm

2 stops14h 35m

San Juan Luis Munoz Marin Intl

Wed 3/4

12:45 pm-11:01 pm

2 stops12h 16m

$295

SpringfieldSan Juan

SPI - SJU

SPISJU

Springfield Capital

Mon 12/1

6:18 pm-5:52 pm

2 stops21h 34m

San Juan Luis Munoz Marin Intl

Wed 12/10

8:20 am-8:09 pm

2 stops13h 49m

$365

SpringfieldSan Juan

SPI - SJU

SPISJU

Springfield Capital

Fri 2/6

2:48 pm-10:48 am

2 stops18h 00m

San Juan Luis Munoz Marin Intl

Wed 2/11

6:00 am-2:55 pm

1 stop10h 55m

$438

SpringfieldSan Juan

SPI - SJU

SPISJU

Springfield Capital

Sat 3/7

6:00 am-10:40 am

2 stops26h 40m

San Juan Luis Munoz Marin Intl

Fri 3/13

6:20 am-11:04 pm

1 stop17h 44m

$478

SpringfieldNassau

SPI - NAS

SPINAS

Springfield Capital

Sun 4/5

6:00 am-6:35 pm

2 stops11h 35m

Nassau Intl

Wed 4/8

7:45 am-11:00 pm

2 stops16h 15m

$639

SpringfieldNassau

SPI - NAS

SPINAS

Springfield Capital

Mon 4/6

6:00 am-9:35 am

2 stops26h 35m

Nassau Intl

Wed 4/8

1:10 pm-11:00 pm

2 stops10h 50m

$639

SpringfieldSaint Thomas Island

SPI - STT

SPISTT

Springfield Capital

Mon 4/6

6:40 pm-4:15 pm

2 stops20h 35m

Saint Thomas Island Cyril E King

Wed 4/8

6:40 pm-5:34 pm

2 stops23h 54m

$689

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/25

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, Illinois to Caribbean Islands?

Currently, May is the cheapest month in which you can book a flight from Springfield, Illinois to Caribbean Islands (average of $140). Flying from Springfield, Illinois to Caribbean Islands in December is currently the most expensive (average of $261). 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 October 28, 2025.
Read through reviews of airlines operating flights from Springfield to Caribbean Islands, such as American Airlines. 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
11,032 reviews

Food

6.4

Crew

8.0

Entertainment

6.9

Comfort

7.2

Boarding

7.5

Overall

7.2

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
11,032 reviews
American Airlines
7.2
Good
11,032 reviews

Food

6.4

Crew

8.0

Entertainment

6.9

Comfort

7.2

Boarding

7.5

Overall

7.2

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 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 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 Islands.

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

    A quick flight from Springfield, Illinois to Caribbean Islands can take about 14h 35m. American Airlines provides one of the quickest options available for as low as $295. Springfield, Illinois and Caribbean Islands are separated by a distance of 2042 mi.

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

    When deciding which route to take from Springfield, Illinois to Caribbean Islands 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 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, Illinois to Caribbean Islands?

    Currently, May is the cheapest month in which you can book a flight from Springfield, Illinois to Caribbean Islands (average of $140). Flying from Springfield, Illinois to Caribbean Islands in December is currently the most expensive (average of $261). 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.

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Top airline flying from Springfield to Caribbean Islands

Discover the top airline 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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$225Average$485FlexibilityNo cancel feeOn-time71%

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