$143 Find Cheap Flights from Springfield to Caribbean Islands

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 Islands departing on 8/19. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Springfield to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$449
Montego Bay
Montego Bay2 stops$362
Oranjestad
Oranjestad2 stops$660
Nassau
Nassau1 stop$596
Providenciales
Providenciales1 stop$629
Punta Cana
Punta Cana2 stops$449
Montego Bay
Montego Bay2 stops$362
Oranjestad
Oranjestad2 stops$660
Nassau
Nassau1 stop$596
Providenciales
Providenciales1 stop$629

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

Sat, Aug 8 - Tue, Aug 18
United Airlines Logo
11:19 am - 8:34 pm
SGF
-
SJU
8h 15m
1 stop
United Airlines Logo
7:00 am - 4:11 pm
SJU
-
SGF
10h 11m
1 stop
$341United Airlines
Sun, Nov 8 - Sat, Nov 14
American Airlines Logo
7:26 pm - 12:55 pm
SGF
-
MBJ
16h 29m
2 stops
American Airlines Logo
4:05 pm - 8:55 am
MBJ
-
SGF
17h 50m
2 stops
$362American Airlines
Sun, Sep 20 - Sat, Sep 26
American Airlines Logo
4:20 pm - 11:00 am
SGF
-
SJU
17h 40m
2 stops
American Airlines Logo
10:16 am - 10:32 pm
SJU
-
SGF
13h 16m
2 stops
$366American Airlines
Fri, Sep 18 - Sat, Sep 26
American Airlines Logo
5:35 pm - 11:02 am
SGF
-
MBJ
17h 27m
2 stops
American Airlines Logo
2:09 pm - 9:08 am
MBJ
-
SGF
18h 59m
2 stops
$367American Airlines
Sun, Sep 20 - Sat, Sep 26
American Airlines Logo
4:20 pm - 11:00 am
SGF
-
SJU
17h 40m
2 stops
American Airlines Logo
10:16 am - 10:32 pm
SJU
-
SGF
13h 16m
2 stops
$384American Airlines
Sat, Oct 10 - Tue, Oct 20
American Airlines Logo
7:48 pm - 3:02 pm
SGF
-
SJU
18h 14m
1 stop
American Airlines Logo
8:35 am - 5:49 pm
SJU
-
SGF
10h 14m
1 stop
$393American Airlines
Tue, Oct 13 - Tue, Oct 20
Delta Logo
11:40 am - 9:59 pm
SGF
-
SJU
9h 19m
1 stop
Delta Logo
2:31 pm - 10:32 pm
SJU
-
SGF
9h 01m
1 stop
$398Delta
Fri, Sep 11 - Sat, Sep 19
United Airlines Logo
6:00 am - 2:44 pm
SGF
-
SJU
7h 44m
1 stop
United Airlines Logo
7:00 am - 4:11 pm
SJU
-
SGF
10h 11m
1 stop
$411United Airlines
Sat, Jul 4 - Fri, Jul 10
Delta Logo
6:00 am - 2:04 pm
SGF
-
NAS
7h 04m
1 stop
Delta Logo
1:16 pm - 6:08 pm
NAS
-
SGF
5h 52m
1 stop
$596Delta
Sun, Dec 6 - Fri, Dec 11
Delta Logo
6:00 am - 12:45 pm
SGF
-
PLS
5h 45m
1 stop
Delta Logo
2:10 pm - 10:32 pm
PLS
-
SGF
9h 22m
1 stop
$629Delta
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 $344, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Springfield to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Springfield to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Springfield to Caribbean Islands is August, when tickets cost $209 (return) on average. On the other hand, the most expensive months are March and July, when the average cost of round-trip tickets is $599 and $496 respectively.

Good to know

Low seasonSeptember
Cheapest flight$143
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Springfield to San Juan

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 airlines 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.
7.9
DeltaOverall score based on 8399 reviews
7.8Entertainment
7.2Food
8.5Crew
8.1Boarding
7.8Comfort
Airline reviews

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

4.0 OkayMichelle, Jun 2026
ATL - PIT
Read more Delta reviews

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Average seat comfort, a drink and chips were provided, early boarding because we checked a carryon at the gate was nice. Ticket pricing shenanigans, including fees to pick a seat, check a bag, and get food onboard - evidence the industry is reinvigorating last century’s strategies- destroys the experience before one ever arrives at the airport. It’s difficult to recognize any value or sustain loyalty in the end-to-end process making air travel more drudgery than pleasure.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

The gate experience at LAX was abysmal (same for the arrival experience two days prior). Despite the LAX -> SAT schedule of two flights daily, our departure gate was at a smaller hub that we had to be bussed to from Terminal 4. Fortunately, I arrived at LAX extra early and had time to spare, but if I had not known, I might have missed my flight. I looked at the LAX airport map in the AA app and there was no indication of the additional boarding process. Lastly the gate area we were bussed to was crowded with limited food and beverage options. On flight, the fight attendant was hospitable and attentive, the flight was smooth, and AA's free (and working) wifi for AA members were all on the positive side.

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.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight back to Dallas was delayed, which has happened to me several times with American Airlines. There was no announcement, no update sent out, no compensation offered for the inconvenience.

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

Our flight from JFK to Madrid was delayed. We had to go from one side of the Madrid airport (Terminal 4s to the far end of terminal 4 - Gate K98) to our gate in less than 30 minutes. Put passport control and security/baggage check and that’s very hard unless you’re Usain Bolt. I called Iberia Airlines and the telephone customer service told me that I was going to have to pay to re-book. Luckily the help desk in the airport (who was dealing with dozens of people from the same JFK-Madrid flight) did not charge us extra to reschedule to a flight 8 hours later. They also gave us a voucher for breakfast and lunch. Glad the actual person at the airport had some actual sense.

As always, most AA flights that we fly are almost ALWAYS delayed and that too multiple times. Very frustrating

Boarding was smooth and seamless and the flight was without incident.

For an long range economy flight I feel more space and more meal options need to be offered for flights over 5 hours

Our flight was repeatedly delayed for maintenance problems: scheduled for 9.30am, eventually delayed to 7pm! Very very inconvenient! AA should have provided a substitute plane much earlier.. On the other hand, Customer Service crew in Charlotte helped us to reach NY (LGA) by late afternoon. Thank you Patricia!! The actual flight was quick and very comfortable. As always a. excellent, professional crew. [no food on a a short hop).

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports