$163 Find Cheap Flights from Springfield to Caribbean - Compare and Save

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 8/19. 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.
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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$541
Montego Bay
Montego Bay2 stops$397
Oranjestad
Oranjestad1 stop$485
Nassau
Nassau1 stop$470
Kingston
Kingston2 stops$769
Providenciales
Providenciales2 stops$823
Punta Cana
Punta Cana2 stops$541
Montego Bay
Montego Bay2 stops$397
Oranjestad
Oranjestad1 stop$485
Nassau
Nassau1 stop$470
Kingston
Kingston2 stops$769
Providenciales
Providenciales2 stops$823

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, Jan 19 - Fri, Jan 22
Delta Logo
11:40 am - 11:50 pm
SGF
-
SJU
10h 10m
1 stop
Delta Logo
6:15 am - 11:11 am
SJU
-
SGF
6h 56m
1 stop
$326Delta
Sun, Sep 20 - Sat, Sep 26
American Airlines Logo
7:36 pm - 1:57 pm
SGF
-
SJU
17h 21m
2 stops
American Airlines Logo
3:35 pm - 9:08 am
SJU
-
SGF
18h 33m
1 stop
$346American Airlines
Sat, Sep 26 - Sat, Oct 3
American Airlines Logo
7:51 pm - 1:57 pm
SGF
-
SJU
17h 06m
2 stops
American Airlines Logo
3:35 pm - 9:08 am
SJU
-
SGF
18h 33m
1 stop
$346American Airlines
Sun, Aug 30 - Tue, Sep 1
American Airlines Logo
6:00 am - 2:54 pm
SGF
-
SJU
7h 54m
1 stop
American Airlines Logo
12:55 am - 10:04 am
SJU
-
SGF
10h 09m
1 stop
$346American Airlines
Sun, Sep 20 - Sat, Sep 26
Delta Logo
6:08 am - 1:45 pm
SGF
-
SJU
6h 37m
1 stop
Delta Logo
2:50 pm - 9:16 pm
SJU
-
SGF
7h 26m
1 stop
$386Delta
Sun, Sep 20 - Sat, Sep 26
Delta Logo
6:08 am - 1:45 pm
SGF
-
SJU
6h 37m
1 stop
Delta Logo
2:50 pm - 9:16 pm
SJU
-
SGF
7h 26m
1 stop
$447Delta
Sat, Aug 29 - Thu, Sep 10
Delta Logo
6:06 am - 3:34 pm
SGF
-
MBJ
9h 28m
1 stop
Delta Logo
1:14 pm - 10:08 pm
MBJ
-
SGF
8h 54m
1 stop
$462Delta
Sun, Aug 30 - Wed, Sep 2
United Airlines Logo
6:25 am - 3:42 pm
SGF
-
SJU
8h 17m
1 stop
United Airlines Logo
7:00 am - 2:16 pm
SJU
-
SGF
8h 16m
1 stop
$466United Airlines
Mon, Dec 7 - Mon, Dec 14
United Airlines Logo
6:35 am - 1:33 pm
SGF
-
NAS
5h 58m
1 stop
United Airlines Logo
2:35 pm - 9:28 pm
NAS
-
SGF
7h 53m
1 stop
$470United Airlines
Mon, Dec 7 - Mon, Dec 14
United Airlines Logo
6:35 am - 1:33 pm
SGF
-
NAS
5h 58m
1 stop
United Airlines Logo
2:35 pm - 10:34 am
NAS
-
SGF
20h 59m
2 stops
$491United 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.

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 February, when tickets cost $507 (return) on average. On the other hand, the most expensive months are June and October, when the average cost of round-trip tickets is $844 and $796 respectively.

Good to know

Low season

September

Cheapest flight

$163
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 25% lower on average.
Flight from Springfield to San Juan

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.
7.8
DeltaOverall score based on 8497 reviews
7.8Comfort
8.1Boarding
8.5Crew
7.2Food
7.8Entertainment
Airline reviews

Your survey needs a N/A option. I didn’t use the entertainment or eat food.

10.0 ExcellentJon, Jul 2026
MCI - SLC
Read more Delta reviews

Your survey needs a N/A option. I didn’t use the entertainment or eat food.

Flight was delayed multiple time and for more than 1 hr. My onward flight from BOS to MCI was also delayed. These delays have caused me so much inconvenience and Delta does nothing to ensure flights take off on time. No one knew why the inbound flight was delayed and what was the issue.

Our flight was delayed by over 4 hours due to a maintenance issue. They announced a new plane was on the way. We were given a $12 food voucher ( airport food is quite expensive You can’t even by a water and a small snack for 12:00. 4 hours later we boarded and landed in Atlanta at 10:20 ish pm. Of course we missed our connection and we were given a hotel voucher and another food voucher ! We didn’t make it home until 11:00 the next day ! Unacceptable

From checking to boarding, it was a seamless experience. The service agents were so helpful. The flight crew was so pleasant.

Delta has too many delays now days. It is 1:06 am now. I was supposed to land in Norfolk at 10:30 pm. I got re-booked through Detroit and I’m still in Detroit. I hope to be landed in Norfolk by 3am. I’ve been in airports for 12 hours as of right now. There is a weather delay now but most delays lately have been maintenance.

This is the first time I've been disappointed with Delta. I was called by Delta to see if I would volunteer to change flights since my original flight home was overbooked. I accepted. The modified booking only provided me a 35 minute layover - when you subtract the fact that boarding closes for a flight 15 minutes early, that gave me 20 minutes to run for one end of the airport to the other. I barely made it. On the 2.5 hour flight to Tampa, the crew repeatedly let us know over the intercom that they cannot serve drinks or snacks due to safety/turbulence. I would have accepted this reason if they did not CONTINUALLY SERVE DRINKS AND COOKED FOOD to First class. If safety is the excuse then the entire plane should be strapped in for safety. On top of this the air conditioning vents were not working correctly and the plane was uncomfortably warm. I love Delta and am a loyal Delta traveler, and I have never had an experience like this. I don't know if there's a disconnect between availability among third-party sites like KAYAK and the airlines or what, but when overbooking causes issues like this for travelers it should be reviewed and changes to the booking process should be made. I blame BOTH KAYAK and Delta for this terrible experience.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

They delayed our flight because of bad weather in NY which was completely understandable. Then they cancelled our flight and a later flight that evening. The earliest we could fly was the next morning. We ended up buying last minute tickets on another airline and made it home slightly delayed but safely that evening. Delta kept saying it was weather related but if that was the case how did we make it back on another airline? The weather in NY was cloudy but not bad.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

Our flight was great with an unexpected upgrade. However, four days into our travel we are still without a piece of luggage. The bag tracker has not been accurate, the airline is not communicating with me or the luggage delivery service and no one is willing to take responsibility or guarantee any kind of support or reimbursement. Unfortunately, we do not have the option to easily shop to replace items as we are currently on a cruise. I have been very disappointed by United Airlines response.

Fine not above and beyond as I had a connection that was delayed due to maintenance

HORRIBLE, my initial flight was cancelled, they made me pay $200 extra dollars and that got cancelled as well! After 6 cancellations I decided to get a refund because I needed to get home to my babies. Out of $1000+ dollars they offered me only $40 in refund! Totally unacceptable! The flight that they cancelled I was able to fly it on another airline. I had to spend $400 on one way tickets just to get home! I’m still getting the runaround.

Flight was delayed. De-icing took a while. When we landed had to wait for another plane to vacate our gate. Just an overall bad experience.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Our flight was understandably diverted to a small regional airport in Laramie, Wyoming due to weather conditions, which I fully recognize and appreciate. However, the low rating stems from the experience that followed: passengers remained on board for over an hour without the option to deplane and stretch, despite the aircraft being stationary. Although the pilot opened the cabin door, only he was permitted to exit. Meanwhile, passengers grew increasingly uncomfortable as warm summer air entered the cabin through the open door, and being in the second row meant we were impacted immediately. While the flight attendants made efforts to keep everyone at ease, I believe allowing passengers to deplane briefly, given the extended delay, would have significantly improved the overall experience.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

Flight was canceled 12 hours before take-off due to “weather”

We were told our seats were switched which put us in row 1 instead of 12. We were not able to keep our personal items with us. This caused us not to be able to have our gum to pop our ears and we weren’t able to get our iPads out due to the seat belt sign never turning off.

My luggage was not sent with us. Not sure if this is Envoy Air responsibility but that was a very BAD experience

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

American delayed the flight for a crew rest period. The delay occurred late in the evening - the earliest i can find is 10:20 pm. With a 6 am flight anyone on the flight would have already have been asleep (unless you are insane, a vampire or on drugs) and at least for me i was already on the way to the airport at 445 am the next morning when i discovered they delayed the flight until 9 am. Given the incoming flight was in the air at 6 pm the evening before this should have been figured out a lot more timely that was there only crew to use. Just frustrating given there is no consideration for customer experience anymore in flying.

Good crew and flight was on time. It’s a small plane with limited overhead luggage space. They said the overhead space was full and I had to check my bag. There was still space when I got on. Waiting for my checked luggage added 30 minutes to my trip. Not the end of the world but also not great.

I very rarely fly American and my experience today reenforces that is the correct decision. While the staff were all very courteous, our flight was first thing in the morning so there was no reason to be delayed, yet appropriate maintenance checks weren’t completed prior to our flight so we were delayed multiple times. Not a great showing, American Airlines.

Trip delayed for 2 hours because of rain. We boarded and have to get down the flight and reboard again.

No enough space plus only allowing one laggage instead of two like other airlines.

Qatar airways ,boarding arrangements at Hamid international airport could been better

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Two flight changes before the scheduled flight. On the day of the flight, the flight was delayed, which caused the connecting flight to be missed. Then, I was directed to another airport (CUN) and traveled to Tulum. American gave a $12 voucher for lunch. The least expensive item on the menu at a Mexican restaurant was $9.99. Driving to Tulum was a bad auto crash, and traffic was delayed two-plus hours. The bottom line is that we should have been at the hotel at noon, but it ended up at 11:30 PM.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports