$152 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 8/29. 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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Cheap Flights from Springfield to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$491
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad2 stops$711
Nassau
Nassau1 stop$440
Kingston
Kingston2 stops$859
Providenciales
Providenciales2 stops$388
Punta Cana
Punta Cana2 stops$491
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad2 stops$711
Nassau
Nassau1 stop$440
Kingston
Kingston2 stops$859
Providenciales
Providenciales2 stops$388

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

Tue, Apr 28 - Tue, May 5
American Airlines Logo
6:00 am - 6:10 pm
SGF
-
SJU
11h 10m
2 stops
American Airlines Logo
6:45 am - 8:46 pm
SJU
-
SGF
15h 01m
1 stop
$351American Airlines
Thu, Apr 23 - Wed, Apr 29
American Airlines Logo
6:24 pm - 11:51 am
SGF
-
MBJ
17h 27m
2 stops
American Airlines Logo
2:29 pm - 9:24 am
MBJ
-
SGF
18h 55m
2 stops
$357American Airlines
Tue, Apr 28 - Tue, May 5
American Airlines Logo
7:08 am - 6:10 pm
SGF
-
SJU
10h 02m
2 stops
American Airlines Logo
6:45 am - 8:46 pm
SJU
-
SGF
15h 01m
1 stop
$357American Airlines
Wed, May 27 - Mon, Jun 1
American Airlines Logo
6:12 pm - 11:45 am
SGF
-
MBJ
17h 33m
2 stops
American Airlines Logo
5:17 pm - 10:57 am
MBJ
-
SGF
17h 40m
2 stops
$362American Airlines
Tue, Apr 28 - Tue, May 5
American Airlines Logo
5:27 pm - 10:48 am
SGF
-
SJU
16h 21m
1 stop
American Airlines Logo
6:45 am - 8:46 pm
SJU
-
SGF
15h 01m
1 stop
$367American Airlines
Tue, May 5 - Tue, May 12
Delta Logo
3:59 pm - 11:13 pm
SGF
-
SJU
6h 14m
1 stop
Delta Logo
2:48 pm - 10:19 pm
SJU
-
SGF
8h 31m
1 stop
$368Delta
Tue, Apr 7 - Tue, Apr 14
United Airlines Logo
6:15 am - 1:47 pm
SGF
-
NAS
6h 32m
1 stop
United Airlines Logo
3:59 pm - 10:04 pm
NAS
-
SGF
7h 05m
1 stop
$440United Airlines
Fri, Apr 17 - Fri, Apr 24
United Airlines Logo
6:00 am - 2:57 pm
SGF
-
NAS
7h 57m
1 stop
United Airlines Logo
3:59 pm - 12:36 am
NAS
-
SGF
9h 37m
1 stop
$465United Airlines
Mon, Jun 8 - Tue, Jun 16
Multiple Airlines Logo
3:26 pm - 4:40 pm
SGF
-
PUJ
24h 14m
1 stop
Multiple Airlines Logo
9:25 am - 12:04 pm
PUJ
-
SGF
27h 39m
1 stop
$537Multiple Airlines
Wed, Aug 26 - Tue, Sep 1
Delta Logo
6:00 am - 11:48 am
SGF
-
NAS
4h 48m
1 stop
Delta Logo
3:00 pm - 10:29 pm
NAS
-
SGF
8h 29m
1 stop
$546Delta
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.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Springfield to Caribbean, 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 is April, when tickets cost $336 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $933 and $869 respectively.

Good to know

Low seasonSeptember
Cheapest flight$152
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly and prices are also 19% lower on average.
Flight from Springfield to Montego Bay

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 3 airlines serving 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.
7.9
DeltaOverall score based on 8286 reviews
7.8Entertainment
8.5Crew
7.9Comfort
7.2Food
8.1Boarding
Airline reviews

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

10.0 ExcellentDebra, Mar 2026
PBI - ATL
Read more Delta reviews

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

OK, we were delayed and had to de plane and reboard.

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Both my flight where delayed Had 25min to make it to my transfer flight

Everything was on time and service on the flight was great!

Wifi Bluetooth features for watching in flight movie was horrible. Screen kept blacking out no connection of sound although it said connected. Other than that smooth trip .

The 777’s economy seat’s legroom was more tolerable than expected. I appreciate the reclining mechanism which slides the seat forward to minimize cannibalizing the space behind. The food was terrible: very salty.

The travel company that you have on your site did me so wrong. I don’t know how it happened, but they put my son‘s name on my plane ticket flying to Vietnam. Along with his birthday. They would not have let me fly from Fort Myers to Ho Chi Minh City. I don’t think that I can ever use your service again. I typed my information into the browser along with my passport number and four days before I’m leaving I have to quickly search another ticket to fly out here.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

The flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

Not really sure I enjoyed the flight at all. The flight attendants seemed a little tired and rude at times. The snacks were lacking in taste and sustenance. The flight was incredibly turbulent for three plus hours and the pilot had to do a second pass to land at our final destination because he was coming in so fast. He must have taken a short cut and because of it we had to suffer the violent turbulence and the dropping down. It had to be one of if not the worse flights I have ever been on and have traveled vastly all over the world.

Delay after delay with little communication then AA lost my luggage and at airport would not assist just said scan this QR code to track your luggage and submit a claim. However QR code provided did not work so have to go back to airport

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

It would have been nice if American tried to care.

American Airlines did everything they could with the high Spring Break crowd. I was frustrated to be changed from 1st class to a middle seat at the back of the plane. This has happened before, not sure booking 1st class and paying the extra actually works.

I booked 1st class, my flights were changed and I was sitting in the middle at the back of the plane. A far cry from the 1st class I purchased for my flights. I am grateful I arrived on time.

Aging planer and NO wifi on a 14 hour day flight. Unless you are retired or don't need to work or be in touch with the world... The lack of Wifif really ruined the flight. And the old plane - really showing it's age, wasn't great

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports