$205 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 8/20. 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

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
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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 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 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

Tue, Aug 19 - Sat, Aug 30
American Airlines Logo
5:00 am - 6:15 pmSGF-SJU
12h 15m2 stops
American Airlines Logo
8:00 am - 8:19 pmSJU-SGF
13h 19m2 stops
$261American Airlines
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Mon, Oct 6 - Wed, Oct 15
American Airlines Logo
7:43 pm - 2:25 pmSGF-SJU
17h 42m1 stop
American Airlines Logo
7:00 am - 7:07 pmSJU-SGF
13h 07m2 stops
$290American Airlines
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Mon, Sep 22 - Sat, Sep 27
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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Fri, Sep 12 - Fri, Sep 19
United Airlines Logo
6:20 pm - 3:25 pmSGF-PUJ
20h 05m2 stops
United Airlines Logo
4:35 pm - 10:50 amPUJ-SGF
19h 15m2 stops
$364United Airlines
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Fri, Sep 12 - Fri, Sep 19
United Airlines Logo
6:20 pm - 2:24 pmSGF-PUJ
19h 04m1 stop
United Airlines Logo
4:35 pm - 10:50 amPUJ-SGF
19h 15m2 stops
$371United Airlines
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Mon, Aug 11 - Thu, Aug 21
 Logo
1:21 pm - 3:10 pmSGF-STT
24h 49m2 stops
 Logo
12:18 pm - 8:14 amSTT-SGF
20h 56m2 stops
Sun, Jan 11 - Wed, Jan 21
Delta Logo
6:00 am - 3:15 pmSGF-MBJ
8h 15m1 stop
Delta Logo
12:35 pm - 9:41 pmMBJ-SGF
10h 06m1 stop
$515Delta
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Mon, Aug 11 - Thu, Aug 21
 Logo
12:11 pm - 12:30 pmSGF-STT
23h 19m3 stops
 Logo
12:18 pm - 8:14 amSTT-SGF
20h 56m2 stops
Sun, Dec 21 - Thu, Dec 25
LATAM Airlines Logo
5:03 pm - 3:15 pmSGF-PUJ
20h 12m2 stops
LATAM Airlines Logo
2:45 am - 10:09 pmPUJ-SGF
21h 24m2 stops
$2,790LATAM Airlines
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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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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 $453, 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 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 Islands?

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

If your flying dates are flexible, you should consider flying to Caribbean Islands on a Thursday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Springfield to Caribbean Islands. For your return ticket, we recommend flying on a Friday and avoiding Sundays for the best deals.

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

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 Islands, 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 Islands, 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$205
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 Saint Thomas Island

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.

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

    The cheapest time of day to fly to Caribbean Islands 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 Islands 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 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.
8.0
DeltaOverall score based on 7980 reviews
8.5Crew
7.9Entertainment
8.2Boarding
7.9Comfort
7.3Food
Airline reviews

Delayed and took off even later than the scheduled delay time

8.0 ExcellentAnonymous, Jul 2025DTW - SEA
Read more Delta reviews

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.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

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.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

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"

The plane was broken so we had to change planes.

The flight got delayed 2.5 hrs due to a maintenance issue that cause a domino effect. American should have spare planes for when something like this happens.

Everything you need to know for your flight to Caribbean Islands

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