$118 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 1/26. 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$404
Santo Domingo
Santo Domingo2 stops$582
Montego Bay
Montego Bay1 stop$473
Oranjestad
Oranjestad1 stop$586
Nassau
Nassau1 stop$445
Simpson Bay
Simpson Bay1 stop$536
Providenciales
Providenciales2 stops$369
Port of Spain
Port of Spain2 stops$563
Bridgetown
Bridgetown1 stop$606
George Town
George Town2 stops$417
St. John's
St. John's2 stops$604
Aguadilla
Aguadilla2 stops$235
Punta Cana
Punta Cana1 stop$404
Santo Domingo
Santo Domingo2 stops$582
Montego Bay
Montego Bay1 stop$473
Oranjestad
Oranjestad1 stop$586
Nassau
Nassau1 stop$445
Simpson Bay
Simpson Bay1 stop$536
Providenciales
Providenciales2 stops$369
Port of Spain
Port of Spain2 stops$563
Bridgetown
Bridgetown1 stop$606
George Town
George Town2 stops$417
St. John's
St. John's2 stops$604
Aguadilla
Aguadilla2 stops$235

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, Jan 20 - Tue, Jan 27
Delta Logo
11:31 am - 11:45 pm
MSN
-
SJU
10h 14m2 stops
Delta Logo
4:30 pm - 10:50 pm
SJU
-
MSN
8h 20m1 stop
$235Delta
Sat, Jan 24 - Mon, Feb 2
United Airlines Logo
12:32 pm - 12:36 am
MSN
-
SJU
10h 04m2 stops
United Airlines Logo
2:05 am - 12:03 pm
SJU
-
MSN
11h 58m2 stops
$256United Airlines
Sat, Jan 24 - Tue, Jan 27
United Airlines Logo
12:32 pm - 12:36 am
MSN
-
SJU
10h 04m2 stops
United Airlines Logo
8:35 am - 4:44 pm
SJU
-
MSN
10h 09m1 stop
$265United Airlines
Thu, Jan 22 - Tue, Jan 27
American Airlines Logo
11:23 am - 10:26 pm
MSN
-
SJU
9h 03m1 stop
American Airlines Logo
3:49 pm - 11:47 pm
SJU
-
MSN
9h 58m1 stop
$268American Airlines
Thu, Jan 29 - Tue, Feb 3
American Airlines Logo
7:25 am - 8:50 pm
MSN
-
SJU
11h 25m2 stops
American Airlines Logo
6:05 am - 6:44 pm
SJU
-
MSN
14h 39m1 stop
$298American Airlines
Fri, Jan 23 - Mon, Jan 26
American Airlines Logo
11:29 am - 9:39 pm
MSN
-
SJU
8h 10m1 stop
American Airlines Logo
6:00 am - 12:46 pm
SJU
-
MSN
8h 46m1 stop
$301American Airlines
Fri, Jan 2 - Wed, Jan 21
American Airlines Logo
8:10 pm - 5:00 am
MSN
-
SJU
6h 50m1 stop
American Airlines Logo
6:30 am - 4:20 pm
SJU
-
MSN
11h 50m1 stop
$317American Airlines
Thu, Jan 22 - Fri, Jan 30
United Airlines Logo
7:28 am - 9:26 pm
MSN
-
SJU
11h 58m2 stops
United Airlines Logo
2:05 am - 11:51 am
SJU
-
MSN
11h 46m2 stops
$325United Airlines
Tue, Mar 3 - Tue, Mar 10
Delta Logo
5:38 am - 3:30 pm
MSN
-
PUJ
7h 52m1 stop
Delta Logo
2:30 pm - 10:58 pm
PUJ
-
MSN
9h 28m1 stop
$430Delta
Thu, Jan 15 - Mon, Jan 19
Copa Airlines Logo
8:15 am - 11:32 am
MSN
-
SDQ
25h 17m2 stops
Copa Airlines Logo
7:05 pm - 7:07 pm
SDQ
-
MSN
26h 02m2 stops
$766Copa Airlines
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 $619 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$118
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 14% 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.

  • 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 50% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $701.

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 8014 reviews
7.9Entertainment
8.5Crew
8.1Boarding
7.9Comfort
7.3Food
Airline reviews

Did not realize internet screen was hidden between seats and no info printed!!!!

6.0 GoodAnonymous, Dec 2025
BOS - MSP
Read more Delta reviews

Did not realize internet screen was hidden between seats and no info printed!!!!

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

The flight was delayed for about 2 hrs. Other than it, it was good.

Advertised fruit trays with cheese, but only snacks handed out!

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Pushed back only to get deplaned due to a tire damaged by ground crew. They did at least go pretty fast. The bathrooms should be banned under the Geneva convention. No room to even sit straight on the toilet. The under-seat entertainment units block what little leg room there is.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Sat next to a one year old. She crawled all over the place and made me laugh.

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

They did the one thing that really matters - got to Chicago early.

I liked the snacks and the flight attendants were friendly.

Gate agent at Frankfurt was terrible. She denied PRE boarding even as it was printed on the boarding pass. Refused to look at the boarding pass and literally shouting for no reason. Frankfurt airport has horrible and rude staff who avoids trying to answer any question at all. Overall, horrible experience.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

I requested a low sodium meal. Reason being, I take medicine for high blood pressure and I wear compression socks on long flights to help with leg swelling. Having less sodium in meals really helps me feel better on long flights. I received my initial low sodium meal after takeoff. Just before landing, the crew came through with the meal cart and offered me what was being served. I said no thank you and then noticed my low sodium meal in the meal cart, with my name and seat assignment on it. I motioned to the crew member, but he grabbed the meal cart and proceeded to move to the rear of the aircraft. He didn’t see me or other passengers who had attempted to get this attention. He was more concerned about completing meal service since we were due to land in under 45 minutes. I pressed the call light five times from my seat to receive help, but no crew member responded to me. So, I didn’t receive a second meal, one that I requested (the low sodium option). This led me to have a migraine from only eating one meal on an 11-hour flight. This is why I’m not a fan of flying US-based airlines overseas. The crew members continue to show the absolute worst customer service experience. I would not recommend flying American for overseas flights.

WiFi didn’t work the entire flight. Very disappointing. Minimal food and options - sadly the state of current affairs. All other aspects of the flight were fine.

Great flight - friendly and attentive team! Seats in coach were comfy, but a little cramped - but that is the case with all airlines ;)

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

I don’t know who decides what food to serve on these flights but I would be so embarrassed if I served this to anyone and call it food…

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Not great. Booked Extra seats and got nothing extra at all. It’s basically a big budget airline.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports