$256 Find Cheap Flights from Springfield to Caribbean

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Springfield to Caribbean departing on 5/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Book Cheap Springfield to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Springfield to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Springfield to Caribbean

Mon, May 4 - Sat, May 9
American Airlines Logo
2:49 pm - 12:03 pm
SPI
-
SJU
20h 14m
2 stops
American Airlines Logo
7:25 am - 11:38 pm
SJU
-
SPI
17h 13m
2 stops
$256American Airlines
Mon, May 4 - Sat, May 9
American Airlines Logo
5:45 am - 2:20 pm
SPI
-
SJU
7h 35m
1 stop
American Airlines Logo
7:25 am - 11:38 pm
SJU
-
SPI
17h 13m
2 stops
$319American Airlines
Mon, May 4 - Sat, May 9
American Airlines Logo
5:45 am - 2:20 pm
SPI
-
SJU
7h 35m
1 stop
American Airlines Logo
3:09 pm - 11:38 pm
SJU
-
SPI
9h 29m
1 stop
$441American Airlines
Thu, Mar 5 - Sun, Mar 8
American Airlines Logo
5:00 am - 9:49 pm
SPI
-
SJU
14h 49m
2 stops
American Airlines Logo
6:00 am - 11:32 pm
SJU
-
SPI
18h 32m
2 stops
$619American Airlines
Thu, Mar 5 - Sun, Mar 8
American Airlines Logo
6:54 pm - 5:24 am
SPI
-
SJU
8h 30m
1 stop
American Airlines Logo
6:00 am - 11:32 pm
SJU
-
SPI
18h 32m
2 stops
$620American Airlines
Fri, Mar 13 - Mon, Mar 16
American Airlines Logo
6:37 pm - 3:36 pm
SPI
-
NAS
19h 59m
2 stops
American Airlines Logo
1:56 pm - 11:32 pm
NAS
-
SPI
10h 36m
1 stop
$632American Airlines
Fri, Mar 13 - Mon, Mar 16
American Airlines Logo
5:00 am - 1:00 pm
SPI
-
NAS
7h 00m
1 stop
American Airlines Logo
1:56 pm - 11:32 pm
NAS
-
SPI
10h 36m
1 stop
$699American Airlines
Thu, Mar 5 - Sun, Mar 8
American Airlines Logo
5:00 am - 9:49 pm
SPI
-
SJU
14h 49m
2 stops
American Airlines Logo
7:40 am - 11:32 pm
SJU
-
SPI
16h 52m
2 stops
$711American Airlines
Thu, Mar 5 - Sun, Mar 8
American Airlines Logo
5:00 am - 9:49 pm
SPI
-
SJU
14h 49m
2 stops
American Airlines Logo
7:11 am - 11:32 pm
SJU
-
SPI
17h 21m
2 stops
$715American Airlines
Thu, Mar 5 - Sun, Mar 8
American Airlines Logo
6:54 pm - 5:24 am
SPI
-
SJU
8h 30m
1 stop
American Airlines Logo
6:00 am - 11:32 pm
SJU
-
SPI
18h 32m
2 stops
$754American Airlines
Booking Insights

KAYAK's insights & trends for Springfield to Caribbean flights

Get data-powered insights and trends into flights from Springfield to Caribbean to help you find the cheapest flights, the best time to fly and much more.

How long does a flight from Springfield to Caribbean take?

The duration of a flight to Caribbean depends on your arrival airport. The shortest route to Caribbean from Springfield is to Saint Thomas Island, which takes 20h 54m.

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Springfield to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Springfield to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Springfield to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Springfield to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Springfield to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Springfield to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Springfield to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Springfield to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Springfield to Caribbean

 
Need help choosing which airline to fly with from Springfield to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 11267 reviews
7.2Comfort
8.0Crew
6.4Food
7.5Boarding
6.9Entertainment
Airline reviews

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

2.0 MediocreAndrew, Feb 2026
ORD - LGA
Read more American Airlines reviews

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

The seats from lax to DFW was so tight that I could not move my legs . No WiFi and had to pay . Not a good selection of entertainment

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Kayak was among the missing. There was not the usual advice regarding next gate after arriving in Dallas. No communication after the reminder to check in before the Moline flight. What happened?

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports