$452 Find Cheap Flights from Springfield to Caribbean Islands - Compare and Save

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 8/4. 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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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

Tue, Aug 4 - Mon, Aug 10
American Airlines Logo
6:00 am - 11:48 pm
SPI
-
SJU
16h 48m
1 stop
American Airlines Logo
12:55 am - 2:21 pm
SJU
-
SPI
14h 26m
1 stop
$452American Airlines
Tue, Oct 6 - Wed, Oct 14
American Airlines Logo
2:59 pm - 11:18 am
SPI
-
NAS
19h 19m
2 stops
American Airlines Logo
10:27 am - 12:09 am
NAS
-
SPI
14h 42m
2 stops
$482American Airlines
Tue, Aug 4 - Mon, Aug 10
American Airlines Logo
6:00 am - 9:59 pm
SPI
-
SJU
14h 59m
2 stops
American Airlines Logo
12:55 am - 2:21 pm
SJU
-
SPI
14h 26m
1 stop
$498American Airlines
Tue, Aug 4 - Tue, Aug 11
American Airlines Logo
6:00 am - 9:59 pm
SPI
-
SJU
14h 59m
2 stops
American Airlines Logo
7:30 am - 12:12 am
SJU
-
SPI
17h 42m
2 stops
$582American Airlines
Wed, Dec 2 - Tue, Dec 8
American Airlines Logo
2:59 pm - 10:35 am
SPI
-
SJU
17h 36m
2 stops
American Airlines Logo
2:05 pm - 12:09 am
SJU
-
SPI
12h 04m
2 stops
$654American Airlines
Wed, Dec 2 - Tue, Dec 8
American Airlines Logo
6:02 am - 2:57 pm
SPI
-
SJU
6h 55m
1 stop
American Airlines Logo
3:47 pm - 12:09 am
SJU
-
SPI
10h 22m
1 stop
$776American Airlines
Tue, Oct 6 - Wed, Oct 14
American Airlines Logo
6:02 am - 5:56 pm
SPI
-
NAS
10h 54m
2 stops
American Airlines Logo
2:08 pm - 12:09 am
NAS
-
SPI
11h 01m
3 stops
$2,291American 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 $274, prices are generally cheapest when you fly direct.

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 11809 reviews
6.8Entertainment
7.9Crew
6.4Food
7.5Boarding
7.2Comfort
Airline reviews

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

2.0 MediocreAnonymous, Jul 2026
ORD - BWI
Read more American Airlines reviews

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports