$326 Find Cheap Flights from Springfield to Caribbean Islands

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 Islands departing on 5/10. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Springfield to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Springfield to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Book Cheap Springfield to Caribbean Islands 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 Islands 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 Islands

Sun, May 10 - Fri, May 15
American Airlines Logo
5:45 am - 2:18 pm
SPI
-
SJU
7h 33m
1 stop
American Airlines Logo
7:25 am - 11:43 pm
SJU
-
SPI
17h 18m
2 stops
$326American Airlines
Sun, May 10 - Fri, May 15
American Airlines Logo
2:49 pm - 10:48 am
SPI
-
SJU
18h 59m
2 stops
American Airlines Logo
11:43 am - 11:43 pm
SJU
-
SPI
13h 00m
2 stops
$366American Airlines
Sun, May 10 - Fri, May 15
American Airlines Logo
5:45 am - 2:18 pm
SPI
-
SJU
7h 33m
1 stop
American Airlines Logo
3:08 pm - 11:43 pm
SJU
-
SPI
9h 35m
1 stop
$369American Airlines
Sun, May 10 - Fri, May 15
American Airlines Logo
2:49 pm - 10:48 am
SPI
-
SJU
18h 59m
2 stops
American Airlines Logo
3:08 pm - 11:43 pm
SJU
-
SPI
9h 35m
1 stop
$379American Airlines
Sun, May 10 - Fri, May 15
American Airlines Logo
5:45 am - 2:18 pm
SPI
-
SJU
7h 33m
1 stop
American Airlines Logo
3:08 pm - 11:43 pm
SJU
-
SPI
9h 35m
1 stop
$406American Airlines
Sun, May 10 - Fri, May 15
American Airlines Logo
5:45 am - 2:18 pm
SPI
-
SJU
7h 33m
1 stop
American Airlines Logo
3:08 pm - 11:43 pm
SJU
-
SPI
9h 35m
1 stop
$412American Airlines
Sun, May 10 - Fri, May 15
American Airlines Logo
5:45 am - 2:18 pm
SPI
-
SJU
7h 33m
1 stop
American Airlines Logo
3:08 pm - 11:43 pm
SJU
-
SPI
9h 35m
1 stop
$418American Airlines
Wed, Aug 12 - Sat, Aug 15
American Airlines Logo
6:00 am - 6:15 pm
SPI
-
SJU
11h 15m
2 stops
American Airlines Logo
8:00 am - 11:04 pm
SJU
-
SPI
16h 04m
2 stops
$466American Airlines
Sun, May 10 - Fri, May 15
American Airlines Logo
5:45 am - 2:18 pm
SPI
-
SJU
7h 33m
1 stop
American Airlines Logo
3:08 pm - 11:43 pm
SJU
-
SPI
9h 35m
1 stop
$468American Airlines
Sat, Apr 25 - Wed, Apr 29
American Airlines Logo
2:49 pm - 10:48 am
SPI
-
SJU
18h 59m
2 stops
American Airlines Logo
3:10 pm - 11:38 pm
SJU
-
SPI
9h 28m
1 stop
$490American Airlines
Booking Insights

KAYAK's insights & trends for Springfield to Caribbean Islands flights

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

Can I save money by flying with a layover from Springfield to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $318, prices are generally cheapest when you fly direct.

Find deals

FAQs - booking Caribbean Islands flights

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

    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 Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Springfield to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands 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 Islands

 
See real verified KAYAK customer reviews for airlines flying from Springfield to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Springfield to Caribbean Islands? 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.
7.1
American AirlinesOverall score based on 11569 reviews
6.9Entertainment
7.5Boarding
6.4Food
7.9Crew
7.2Comfort
Airline reviews

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

4.0 OkayMichelle, Apr 2026
ORD - TYS
Read more American Airlines reviews

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Springfield (SPI)