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Caribbean

$500+ 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 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
SPI — SJU
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/27. 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.
Sun 2/16:00 am
SPI
-
SJU
2 stops9h 03m
American Airlines
Sun 2/156:33 am
SJU
-
SPI
1 stop13h 50m
American Airlines
Deal found 1/27$500
This American Airlines deal was found by Cheapflights users on 1/28. 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 5/262:50 pm
SPI
-
STT
2 stops19h 07m
American Airlines
Sat 5/3012:50 pm
STT
-
SPI
2 stops11h 49m
American Airlines
Deal found 1/28$1,147

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 January 29, 2026.

Round-trip from

$1,147
(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 January 29, 2026.
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

SpringfieldSaint Thomas Island

SPI - STT

SPISTT

Springfield Capital

Tue 5/26

2:50 pm-10:57 am

2 stops19h 07m

Saint Thomas Island Cyril E King

Sat 5/30

12:50 pm-11:39 pm

2 stops11h 49m

$1,147

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

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 $143). Flying from Springfield, Illinois to Caribbean in June is currently the most expensive (average of $253). 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 January 29, 2026.
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
11,206 reviews

Crew

8.0

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Food

6.4

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,206 reviews
American Airlines
7.2
Good
11,206 reviews

Crew

8.0

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Food

6.4

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 19h 07m. Your travel time can differ by up to . The distance from Springfield, Illinois to Caribbean is about 2090 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 - Saint Thomas Island Cyril E King, Springfield Capital - Nassau Intl or Springfield Capital - San Juan Luis Munoz Marin Intl 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 $143). Flying from Springfield, Illinois to Caribbean in June is currently the most expensive (average of $253). 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$225Average$609FlexibilityNo cancel feeOn-time71%

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