$144 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 8/22. 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

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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 Cana1 stop$360
Montego Bay
Montego Bay1 stop$502
Oranjestad
Oranjestad2 stops$615
Nassau
Nassau2 stops$544
Kingston
Kingston1 stop$651
Providenciales
Providenciales1 stop$468
Punta Cana
Punta Cana1 stop$360
Montego Bay
Montego Bay1 stop$502
Oranjestad
Oranjestad2 stops$615
Nassau
Nassau2 stops$544
Kingston
Kingston1 stop$651
Providenciales
Providenciales1 stop$468

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

Mon, Nov 10 - Thu, Nov 20
United Airlines Logo
9:00 am - 9:26 pmSGF-SJU
10h 26m1 stop
United Airlines Logo
8:10 am - 2:39 pmSJU-SGF
8h 29m1 stop
$258United Airlines
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Tue, Jan 13 - Fri, Jan 16
American Airlines Logo
5:49 am - 8:50 pmSGF-SJU
13h 01m2 stops
American Airlines Logo
7:20 am - 7:19 pmSJU-SGF
13h 59m1 stop
$290American Airlines
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Sat, Jan 24 - Sat, Jan 31
American Airlines Logo
4:34 pm - 11:45 amSGF-SJU
17h 11m1 stop
American Airlines Logo
7:20 am - 4:25 pmSJU-SGF
11h 05m1 stop
$295American Airlines
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Tue, Aug 26 - Sat, Aug 30
American Airlines Logo
5:00 am - 2:25 pmSGF-SJU
8h 25m1 stop
American Airlines Logo
8:00 am - 8:19 pmSJU-SGF
13h 19m2 stops
$297American Airlines
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Mon, Nov 10 - Thu, Nov 20
United Airlines Logo
9:00 am - 9:26 pmSGF-SJU
10h 26m1 stop
United Airlines Logo
8:30 am - 5:46 pmSJU-SGF
11h 16m2 stops
$358United Airlines
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Mon, Sep 15 - Mon, Sep 22
Delta Logo
6:00 am - 2:32 pmSGF-PUJ
7h 32m1 stop
Delta Logo
3:59 pm - 10:02 pmPUJ-SGF
7h 03m1 stop
$360Delta
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Sat, Aug 30 - Sat, Sep 6
Delta Logo
6:00 am - 3:10 pmSGF-STT
8h 10m1 stop
Delta Logo
3:23 pm - 10:05 pmSTT-SGF
7h 42m1 stop
$524Delta
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Sat, Nov 8 - Sat, Nov 15
LATAM Airlines Logo
3:23 pm - 5:45 pmSGF-AUA
24h 22m2 stops
LATAM Airlines Logo
6:45 pm - 11:07 amAUA-SGF
18h 22m2 stops
$2,833LATAM Airlines
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Sat, Nov 8 - Sun, Nov 16
LATAM Airlines Logo
3:23 pm - 5:45 pmSGF-AUA
24h 22m2 stops
LATAM Airlines Logo
6:45 pm - 6:08 pmAUA-SGF
25h 23m2 stops
$3,060LATAM Airlines
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Thu, Nov 6 - Sun, Nov 16
WestJet Logo
11:44 am - 3:40 pmSGF-AUA
25h 56m2 stops
WestJet Logo
4:30 pm - 2:50 pmAUA-SGF
24h 20m2 stops
$4,005WestJet
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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 $315 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $882 and $869 respectively.

What’s the cheapest day of the week to fly from Springfield to Caribbean?

The average price of all round-trip flights from Springfield to Caribbean clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Springfield to Caribbean, look for departures on Thursdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Caribbean, Friday is the cheapest day to fly and Sunday is the most expensive.

How far in advance should I book a flight from Springfield to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Springfield to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.


Good to know

Low seasonJune
Cheapest flight$144
Best time to beat the crowds but there is an average 23% increase in price.
Most popular time to fly with an average 6% increase in price.
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.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally in the evening, when round-trip flights cost $370 on average. Morning departures are around 60% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally at night, which is peak travel time and where the average cost of a ticket is $789.

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.
8.0
DeltaOverall score based on 7981 reviews
7.3Food
8.2Boarding
8.5Crew
7.9Entertainment
7.9Comfort
Airline reviews

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

2.0 MediocreGim, Jul 2025BGM - DTW
Read more Delta reviews

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Terrible. Delayed 7 hours, and cancelled the flight, leaving me stranded and out of pocket $500 for an alternative last minute flight

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

the delay for 3 hours was understandable due to weather conditions but the flight should’ve provided some on flight compensations or at least provide more food.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

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.

I never flew. Flight was canceled. DIA worst airport in the country. Avoid at all costs.

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

The best airline I have ever travel , really good customer service, attention and service !!

United could have one single once of customer service. No human United employee would help me with the invalid mileage plus number, they said I had to speak with the computer.

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

We had to turn around and head back to Manchester. Problem with a plane engine.

Flight was delayed. Staff at the gate effectively and proactively communicated about the delay.

Very poor delay in dfw was really bad n long

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

Everything you need to know for your flight to Caribbean

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