$374 Find Cheap Flights from Springfield to Caribbean - 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 departing on 8/13. 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

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Useful Info
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

Thu, Aug 13 - Sat, Aug 29
American Airlines Logo
2:51 pm - 11:15 pm
SPI
-
SJU
7h 24m
1 stop
American Airlines Logo
12:55 am - 2:06 pm
SJU
-
SPI
14h 11m
1 stop
$374American Airlines
Fri, Aug 14 - Fri, Aug 21
American Airlines Logo
6:08 am - 11:15 pm
SPI
-
SJU
16h 07m
1 stop
American Airlines Logo
3:47 pm - 2:17 pm
SJU
-
SPI
23h 30m
2 stops
$412American Airlines
Thu, Aug 13 - Sun, Aug 30
American Airlines Logo
2:51 pm - 9:43 am
SPI
-
SJU
17h 52m
2 stops
American Airlines Logo
7:30 am - 12:12 am
SJU
-
SPI
17h 42m
2 stops
$421American Airlines
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
Wed, Aug 5 - Tue, Aug 11
American Airlines Logo
2:51 pm - 11:15 pm
SPI
-
SJU
7h 24m
1 stop
American Airlines Logo
12:55 am - 2:21 pm
SJU
-
SPI
14h 26m
1 stop
$457American Airlines
Wed, Aug 5 - Wed, Aug 12
American Airlines Logo
6:08 am - 11:15 pm
SPI
-
SJU
16h 07m
1 stop
American Airlines Logo
7:30 am - 12:12 am
SJU
-
SPI
17h 42m
2 stops
$496American 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
Wed, Aug 5 - Wed, Aug 12
American Airlines Logo
6:08 am - 6:33 pm
SPI
-
SJU
11h 25m
2 stops
American Airlines Logo
7:30 am - 12:12 am
SJU
-
SPI
17h 42m
2 stops
$581American 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
Sat, Jul 18 - Wed, Jul 22
American Airlines Logo
2:44 pm - 10:01 am
SPI
-
NAS
18h 17m
2 stops
American Airlines Logo
12:29 pm - 12:09 am
NAS
-
SPI
12h 40m
1 stop
$768American Airlines
Useful Info

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.
7.1
American AirlinesOverall score based on 11785 reviews
6.8Entertainment
7.2Comfort
6.4Food
7.9Crew
7.5Boarding
Airline reviews

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.

4.0 OkayDoug, Jul 2026
ORD - PHX
Read more American Airlines reviews

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

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

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

Information on your arrival and departure airports