$145 Find Cheap Flights from Madison to Caribbean Islands - Compare and Save

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Cheap Flights from Madison to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$556
Santo Domingo
Santo Domingo2 stops$625
Montego Bay
Montego Bay1 stop$392
Oranjestad
Oranjestad2 stops$452
Nassau
Nassau1 stop$478
Simpson Bay
Simpson Bay2 stops$564
Providenciales
Providenciales1 stop$435
Port of Spain
Port of Spain2 stops$1,387
George Town
George Town2 stops$427
Aguadilla
Aguadilla2 stops$471
St. John's
St. John's2 stops$813
Punta Cana
Punta Cana1 stop$556
Santo Domingo
Santo Domingo2 stops$625
Montego Bay
Montego Bay1 stop$392
Oranjestad
Oranjestad2 stops$452
Nassau
Nassau1 stop$478
Simpson Bay
Simpson Bay2 stops$564
Providenciales
Providenciales1 stop$435
Port of Spain
Port of Spain2 stops$1,387
George Town
George Town2 stops$427
Aguadilla
Aguadilla2 stops$471
St. John's
St. John's2 stops$813
Booking Insights

KAYAK's insights & trends for Madison to Caribbean Islands flights

Get data-powered insights and trends into flights from Madison 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 Madison to Caribbean Islands?

No, with an average price for the route of $472, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Madison to Caribbean Islands is May, when tickets cost $581 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $790 and $745 respectively.

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

To get a below average price on the flight from Madison to Caribbean Islands, you should book around 2 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low season

September

Cheapest flight

$145
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly with an average 7% increase in price.
Flight from Madison to Nassau

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Madison 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 Madison to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Madison to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Madison 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 Madison 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 Madison 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 Madison 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 Madison 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 3 airlines serving from Madison to Caribbean Islands

 
Need help choosing which airline to fly with from Madison 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.
7.8
DeltaOverall score based on 8564 reviews
7.2Food
8.1Boarding
8.5Crew
7.8Entertainment
7.8Comfort
Airline reviews

Flight was delayed at airport with large backlog and WiFi was spotty

6.0 GoodAnn, Sep 2026
Read more Delta reviews

Flight was delayed at airport with large backlog and WiFi was spotty

The flights were on time; all went as expected which is a big positive! No delays! There was no food or drink service in any legs, which I understand due to the short flight time.

The Delta assistsed services were awesome for my aunt. So very helpful.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Pretty standard flight. Delta has a good selection of movies.

The flight was so late that I had to change connecting flights, turning a five-hour trip into a fourteen-hour nightmare.

Despite being delayed, we would still give a high score for this flight experience. For the first time in quite some time we had excellent customer service throughout our entire round trip. The flight attendants were the most polite we have experienced in our last ten flights at least (non of which were Delta and include business class). The food offered was a better selection than most—we just didn’t have any of it. Overall, almost as good as flying used to be. Thank you to Delta.

Very disappointing that on an international business class flight they would not give me access to the lounge in Boston. They said it was because it was a codeshare flight. International business class should include lounge access regardless of codeshare.

They did not have free WIFI and I was not okay with that!

Food was very bad Crew was not so welcoming. Chairs was so uncomfortable

Flight was on time, clean, etc. Despite connecting to your wi fi I was unable to use your app to watch entertainment.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

All good except paid for wifi that did not work

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

American Airlines put the food on the wrong plane which had already taken off by the time we took off so we had no food on the plane.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

There were several different delays but we ended up being delayed a total of 40 mins or so. It was annoying we had a gate change which made it take longer to leave DFW, and we had to check our carry on. Ugh

The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.

Our flight was changed from Madison to DC to Madison to Charlotte.

We were told we had no flights before our flight was continually delayed then cancelled.

Boarding was relatively fast and easy and the crew was attentive throughout.

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental