$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$539
Montego Bay
Montego Bay1 stop$524
Oranjestad
Oranjestad1 stop$539
Nassau
Nassau1 stop$440
Simpson Bay
Simpson Bay1 stop$615
Providenciales
Providenciales1 stop$363
Bridgetown
Bridgetown1 stop$627
George Town
George Town1 stop$477
St. John's
St. John's2 stops$810
Aguadilla
Aguadilla2 stops$593
Punta Cana
Punta Cana1 stop$439
Santo Domingo
Santo Domingo1 stop$539
Montego Bay
Montego Bay1 stop$524
Oranjestad
Oranjestad1 stop$539
Nassau
Nassau1 stop$440
Simpson Bay
Simpson Bay1 stop$615
Providenciales
Providenciales1 stop$363
Bridgetown
Bridgetown1 stop$627
George Town
George Town1 stop$477
St. John's
St. John's2 stops$810
Aguadilla
Aguadilla2 stops$593

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
8:15 am - 10:22 pm
MSN
-
SJU
12h 07m
2 stops
United Airlines Logo
8:30 am - 2:57 pm
SJU
-
MSN
8h 27m
1 stop
$256United Airlines
Sun, Mar 8 - Sun, Mar 15
Frontier Logo
6:29 pm - 8:54 am
MSN
-
SJU
13h 25m
1 stop
Frontier Logo
3:08 am - 11:34 am
SJU
-
MSN
9h 26m
1 stop
$280Frontier
Sun, Feb 22 - Tue, Mar 3
United Airlines Logo
3:53 pm - 6:11 am
MSN
-
SJU
12h 18m
2 stops
United Airlines Logo
8:30 am - 2:57 pm
SJU
-
MSN
8h 27m
1 stop
$304United Airlines
Tue, Mar 3 - Wed, Mar 11
American Airlines Logo
6:00 am - 8:39 pm
MSN
-
SJU
12h 39m
2 stops
American Airlines Logo
6:33 am - 10:50 pm
SJU
-
MSN
17h 17m
1 stop
$319American Airlines
Tue, Apr 14 - Wed, Apr 15
American Airlines Logo
1:05 pm - 10:05 pm
MSN
-
SJU
8h 00m
1 stop
American Airlines Logo
2:42 pm - 11:28 pm
SJU
-
MSN
9h 46m
1 stop
$324American Airlines
Wed, Apr 15 - Tue, Apr 21
Multiple Airlines Logo
6:36 pm - 8:47 am
MSN
-
SJU
13h 11m
1 stop
Multiple Airlines Logo
7:05 pm - 5:56 pm
SJU
-
MSN
23h 51m
1 stop
$339Multiple Airlines
Tue, Mar 3 - Tue, Mar 10
Delta Logo
6:20 am - 4:09 pm
MSN
-
PUJ
7h 49m
1 stop
Delta Logo
2:30 pm - 10:58 pm
PUJ
-
MSN
9h 28m
1 stop
$465Delta
Sun, Feb 15 - Thu, Feb 19
Delta Logo
6:20 am - 4:09 pm
MSN
-
PUJ
7h 49m
1 stop
Delta Logo
4:17 pm - 10:48 pm
PUJ
-
MSN
8h 31m
1 stop
$471Delta
Sat, Jan 31 - Tue, Feb 3
Multiple Airlines Logo
6:16 pm - 2:52 pm
MSN
-
STT
18h 36m
1 stop
Multiple Airlines Logo
3:57 pm - 5:56 pm
STT
-
MSN
27h 59m
1 stop
$511Multiple Airlines
Sat, Mar 28 - Sat, Apr 4
JetBlue Logo
5:30 am - 2:26 pm
MSN
-
SDQ
7h 56m
1 stop
JetBlue Logo
3:55 pm - 10:34 pm
SDQ
-
MSN
7h 39m
1 stop
$650JetBlue
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 $661 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 8089 reviews
8.1Boarding
7.9Comfort
7.8Entertainment
8.5Crew
7.2Food
Airline reviews

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

4.0 OkayJohn, Jan 2026
DAL - ATL
Read more Delta reviews

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

Because I was moved to an exit row, the snacks in economy comfort, the selection of snacks was better.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

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

Easiest airport experience ever in my life at MSP with Delta check-in and flight attendant gave us a bottle of champagne in celebration of our 10-year wedding anniversary, so overall amazing!

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

It would have been better if the flight wasn't delayed by 2.5 hours

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

Delta flight Delay for ,more that two hours i.e original flight was 6.30 PM and it starts at 8.45 PM, When we connect Delta team for meal vouchers as it is late arrival in designation,But we did not get it as per delta policy , which is not good for mid night arrival,

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

Food should be changed in menu Many muslims travels in this airlime they need to add one Halal meal

Delayed, toilets did not flush, pilot parked to far away from Gate

Was happy we finally got upgraded in 1st class. The seat getting old. The cushiness need some improvement.

Yet another flight in which beverage and snack service was skipped. Other that that, firmly mediocre. Landed early, to gate late due to congestion at the gates. Airline's fault or airports fault: unknown.

Ineffective communication with United resulted in lost baggage. Their Baggage Tracing counter at MUC was shut down from 11:00-14:15 on my arrival. Undertrained, underinformed staff had me Running all over MUC to find someone to help me to no avail. Staff was rude, unhelpful, and unable to effectively use the systems they did have operational. They refused to contact United in any way or provide any accommodation or other resources while I waited for my luggage. This has destroyed my downstream itinerary. If they had even the slightest visibility I may have been able to reschedule/plan, but again, their staff provided nothing, and did nothing more than their website, which doesn’t even work on a standard phone browser. Miserable failure at all levels that weren’t associated with the operation of the aircraft.

Miserable. They moved my seat, but canceled the next leg of my flight. I resolved the issue at my transfer, but that resulted in lost luggage that has taken days off my schedule with no resolution. Worse, they fail to interface effectively with Lufthansa, forcing me to bounce between two equally useless help desks. The apps are unable to handle the situation, the bag dropped off the tracker, and while the call centers are polite, they do not provide written information to assist with cross-airline communication.

left on time, reasonable boarding process arrived early luggage came out quickly

Could we please end the loud announcements about credit card offers on your flights? We are trying to sleep, work, watch videos, etc. and if we need a credit card, we will ask for one. Flying is already not what it used to be.

I would like the crew to talk LESS over the PA and specifically about credit card offers. I am trying to work, sleep, watch a movie and the PA was booming about a credit card offer. Could we go back to the days when the customer was more important than selling a credit card?

Enough space,crew was helpful,food was good.The gates are way far especially for travelers with health issues

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

There were no TV screens - even in Business class. 5 delays, and only given $12 meal voucher! Terrible!

It was good. But the gate team made me check my carry on when there was plenty of space for my luggage on the plane. Otherwise our trip was fine.

The entertainment options were at best, fair. It was exactly the same as my outbound flight. It would have been more entertaining if there were some series from Apple TV, HBO, Showtime or other carriers for me to catch up with.

Concern Regarding Significant Gate Delay and Jet Bridge Issue Dear Customer Relations Team, I am writing to express my disappointment with the experience I had on my recent flight AA 2414 on Sunday January 18, 2026. What should have been a routine departure turned into a frustrating and avoidable delay due to an issue with the jet bridge at the gate. As a result, the flight was delayed by approximately 90 minutes while multiple gate changes were attempted. The lack of clear communication during this period made the situation even more challenging. Passengers were left uncertain about the cause of the delay, the expected timeline, and the next steps. This not only disrupted travel plans but also created unnecessary stress for everyone on board. I understand that operational issues can arise, but a malfunctioning jet bridge and the resulting extended delay suggest an area where procedures or equipment maintenance may need attention. I hope you will review this incident to prevent similar disruptions in the future. I would appreciate acknowledgment of this concern and consideration of appropriate compensation for the inconvenience and lost time caused by this delay. Thank you for taking the time to review my experience. I look forward to hearing from you. Sincerely, Dion Dillard

They made me pay $40 to check a bag that was listed as free when I bought my ticket. Then before boarding they offered to check any bags free.

It was a good trip. Flight Attendants were friendly and responsive.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports