$398 Find Cheap Flights from Springfield to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Springfield to Caribbean departing on 6/15. 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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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

Th. 3, Thg. 3 24 - Th. 5, Thg. 3 26
American Airlines Logo
5:00 am - 10:58 pm
SPI
-
SJU
16h 58m
2 stops
American Airlines Logo
7:40 am - 6:03 pm
SJU
-
SPI
11h 23m
2 stops
$512American Airlines
Th. 3, Thg. 3 24 - Th. 3, Thg. 3 31
American Airlines Logo
5:00 am - 10:58 pm
SPI
-
SJU
16h 58m
2 stops
American Airlines Logo
4:25 pm - 11:32 pm
SJU
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SPI
8h 07m
1 stop
$562American Airlines
Th. 2, Thg. 3 23 - Th. 4, Thg. 4 1
American Airlines Logo
6:37 pm - 7:39 pm
SPI
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SJU
24h 02m
2 stops
American Airlines Logo
7:40 am - 6:03 pm
SJU
-
SPI
11h 23m
2 stops
$604American Airlines
Th. 2, Thg. 3 30 - Th. 4, Thg. 4 1
American Airlines Logo
5:00 am - 9:00 am
SPI
-
SJU
27h 00m
2 stops
American Airlines Logo
3:00 pm - 11:32 pm
SJU
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SPI
9h 32m
1 stop
$632American Airlines
CN, Thg. 3 22 - Th. 4, Thg. 4 1
American Airlines Logo
6:37 pm - 8:34 pm
SPI
-
SJU
24h 57m
2 stops
American Airlines Logo
7:11 am - 6:03 pm
SJU
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SPI
11h 52m
2 stops
$650American Airlines
Th. 3, Thg. 3 31 - Th. 4, Thg. 4 1
American Airlines Logo
5:00 am - 3:28 pm
SPI
-
SJU
9h 28m
1 stop
American Airlines Logo
7:40 am - 11:32 pm
SJU
-
SPI
16h 52m
2 stops
$653American Airlines
Th. 2, Thg. 3 23 - Th. 6, Thg. 3 27
American Airlines Logo
6:37 pm - 7:39 pm
SPI
-
SJU
24h 02m
2 stops
American Airlines Logo
7:40 am - 6:03 pm
SJU
-
SPI
11h 23m
2 stops
$654American Airlines
Th. 4, Thg. 3 18 - Th. 3, Thg. 3 31
American Airlines Logo
5:00 am - 8:34 pm
SPI
-
SJU
14h 34m
2 stops
American Airlines Logo
7:40 am - 7:45 pm
SJU
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SPI
13h 05m
2 stops
$686American Airlines
CN, Thg. 3 22 - Th. 3, Thg. 3 31
American Airlines Logo
6:37 pm - 8:34 pm
SPI
-
SJU
24h 57m
2 stops
American Airlines Logo
4:25 pm - 11:32 pm
SJU
-
SPI
8h 07m
1 stop
$700American Airlines
Th. 3, Thg. 3 31 - Th. 5, Thg. 4 2
American Airlines Logo
5:00 am - 3:28 pm
SPI
-
SJU
9h 28m
1 stop
American Airlines Logo
5:28 am - 6:03 pm
SJU
-
SPI
13h 35m
1 stop
$703American 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.

Find deals

Good to know

Cheapest flight$398
Flight from Springfield to Saint Thomas Island

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 11338 reviews
6.9Entertainment
7.2Comfort
8.0Crew
6.4Food
7.5Boarding
Airline reviews

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.

2.0 MediocreThomas, Feb 2026
ORD - CVG
Read more American Airlines reviews

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.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

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

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Springfield (SPI)