$128 Find Cheap Flights from Madison 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 Madison to Caribbean departing on 3/24. 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 Madison to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$439
Santo Domingo
Santo Domingo1 stop$650
Montego Bay
Montego Bay1 stop$488
Oranjestad
Oranjestad1 stop$539
Nassau
Nassau1 stop$404
Simpson Bay
Simpson Bay2 stops$613
Providenciales
Providenciales2 stops$379
Port of Spain
Port of Spain2 stops$737
Bridgetown
Bridgetown2 stops$627
George Town
George Town1 stop$461
St. John's
St. John's2 stops$828
Aguadilla
Aguadilla1 stop$363
Punta Cana
Punta Cana1 stop$439
Santo Domingo
Santo Domingo1 stop$650
Montego Bay
Montego Bay1 stop$488
Oranjestad
Oranjestad1 stop$539
Nassau
Nassau1 stop$404
Simpson Bay
Simpson Bay2 stops$613
Providenciales
Providenciales2 stops$379
Port of Spain
Port of Spain2 stops$737
Bridgetown
Bridgetown2 stops$627
George Town
George Town1 stop$461
St. John's
St. John's2 stops$828
Aguadilla
Aguadilla1 stop$363

Book Cheap Madison 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 Madison 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 Madison to Caribbean

Tue, Feb 24 - Wed, Mar 4
United Airlines Logo
6:30 am - 9:26 pm
MSN
-
SJU
12h 56m
2 stops
United Airlines Logo
8:30 am - 2:07 pm
SJU
-
MSN
7h 37m
1 stop
$256United Airlines
Wed, Apr 8 - Wed, Apr 15
Delta Logo
6:00 am - 2:15 pm
MSN
-
SJU
7h 15m
1 stop
Delta Logo
6:15 am - 4:17 pm
SJU
-
MSN
11h 02m
1 stop
$304Delta
Tue, Apr 14 - Tue, Apr 21
American Airlines Logo
6:10 am - 8:51 pm
MSN
-
SJU
13h 41m
2 stops
American Airlines Logo
7:25 am - 11:01 pm
SJU
-
MSN
16h 36m
1 stop
$319American Airlines
Mon, Apr 20 - Wed, Apr 29
American Airlines Logo
8:25 pm - 2:08 pm
MSN
-
SJU
16h 43m
1 stop
American Airlines Logo
4:30 pm - 11:55 pm
SJU
-
MSN
8h 25m
1 stop
$324American Airlines
Sat, Feb 28 - Tue, Mar 3
United Airlines Logo
5:44 pm - 6:11 am
MSN
-
SJU
10h 27m
2 stops
United Airlines Logo
2:05 am - 11:53 am
SJU
-
MSN
11h 48m
2 stops
$325United Airlines
Wed, Apr 8 - Sat, May 2
Delta Logo
6:00 am - 2:15 pm
MSN
-
SJU
7h 15m
1 stop
Delta Logo
7:15 am - 9:15 pm
SJU
-
MSN
15h 00m
2 stops
$338Delta
Tue, Apr 21 - Tue, Apr 28
United Airlines Logo
6:30 am - 2:44 pm
MSN
-
SJU
7h 14m
1 stop
United Airlines Logo
1:00 am - 10:11 am
SJU
-
MSN
10h 11m
2 stops
$346United Airlines
Thu, Feb 19 - Thu, Feb 26
JetBlue Logo
5:38 am - 2:32 pm
MSN
-
SJU
6h 54m
1 stop
JetBlue Logo
7:30 am - 4:17 pm
SJU
-
MSN
10h 47m
1 stop
$356JetBlue
Sat, Mar 28 - Sat, Apr 4
JetBlue Logo
5:30 am - 1:10 pm
MSN
-
SDQ
6h 40m
1 stop
JetBlue Logo
2:37 pm - 10:34 pm
SDQ
-
MSN
8h 57m
1 stop
$650JetBlue
Mon, Feb 23 - Tue, Mar 3
British Airways Logo
5:17 pm - 2:16 pm
MSN
-
SXM
18h 59m
1 stop
British Airways Logo
4:01 pm - 9:53 am
SXM
-
MSN
19h 52m
1 stop
$737British Airways
Booking Insights

KAYAK's insights & trends for Madison to Caribbean flights

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Madison 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 Madison to Caribbean is September, when tickets cost $310 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $658 and $621 respectively.

How far in advance should I book a flight from Madison 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 Madison 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 Madison to Caribbean, you should book around 2 weeks before departure, which saves you about 14% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$128
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 28% increase in price.
Flight from Madison to San Juan

FAQs - booking Caribbean flights

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

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

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

 
Need help choosing which airline to fly with from Madison 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 8124 reviews
7.2Food
7.9Comfort
8.1Boarding
8.5Crew
7.8Entertainment
Airline reviews

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

2.0 MediocreJulia, Jan 2026
MSP - BOS
Read more Delta reviews

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

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.

First class ticket gets you a choice of chips or nuts. . Just like economy Southwest. Also no screen in the seats. This is first class???!

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

The food was terrible this time. Otherwise pleasant, quiet, on-time.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Flight arrived 30 min early and bag was waiting at the baggage pickup. United Club HNL was one of the nicest in the system

Unfortunately weather delayed our flight waiting for our plane to arrive and due to a little snow time was needed to deice the plane so departure was very delayed and I missed the connecting flight

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

I wish there were outlets to charge my iPhone. The crew was great; we had a female pilot who was great with explaining what was happening and delays,

The flight crew where really good. Better then the crew from BNE to SFO

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.

My flight to London from Philadelphia was cancelled due to weather.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

one crew said "he" didn't serve double alcohol drinks for travelers in exit rows. crew on prior flight did. Is this a AA rule, and the prior crew was being nice? Also, I think we deserve more than a 25% refund for losing first class seats when rescheduling a flight due to weather

It was a little concerning to hear the ground crew arguing with the flight crew over baggage space. Instead of taking them and checking them, they started checking for space in the first class cabin moving items around like the flight crew didn't know what they were doing. I was embarrassed for them.

2 hour delay due to equipment failure. No updates via the app and airport screens (which continued to show a departure time in the past). AA eventually switched planes and the new plane was not catered or cleaned correctly.

I booked an aisle seat and was given a middle. At 6'4" 230lbs, it is not ideal to fly in the middle row for myself and passengers.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports