$125 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 4/25. 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$459
Santo Domingo
Santo Domingo2 stops$613
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$653
Nassau
Nassau1 stop$551
Simpson Bay
Simpson Bay2 stops$499
Providenciales
Providenciales2 stops$403
Port of Spain
Port of Spain2 stops$824
Bridgetown
Bridgetown2 stops$872
George Town
George Town2 stops$384
St. John's
St. John's2 stops$1,537
Aguadilla
Aguadilla2 stops$726
Punta Cana
Punta Cana1 stop$459
Santo Domingo
Santo Domingo2 stops$613
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$653
Nassau
Nassau1 stop$551
Simpson Bay
Simpson Bay2 stops$499
Providenciales
Providenciales2 stops$403
Port of Spain
Port of Spain2 stops$824
Bridgetown
Bridgetown2 stops$872
George Town
George Town2 stops$384
St. John's
St. John's2 stops$1,537
Aguadilla
Aguadilla2 stops$726

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

Mon, Apr 27 - Fri, May 1
United Airlines Logo
6:30 am - 2:44 pm
MSN
-
SJU
7h 14m
1 stop
United Airlines Logo
1:00 am - 10:12 am
SJU
-
MSN
10h 12m
2 stops
$329United Airlines
Wed, Apr 22 - Wed, Apr 29
American Airlines Logo
11:35 am - 8:51 pm
MSN
-
SJU
8h 16m
1 stop
American Airlines Logo
6:00 am - 11:28 pm
SJU
-
MSN
18h 28m
1 stop
$331American Airlines
Wed, Apr 22 - Tue, Apr 28
United Airlines Logo
10:05 am - 9:24 pm
MSN
-
SJU
10h 19m
2 stops
United Airlines Logo
1:00 am - 10:11 am
SJU
-
MSN
10h 11m
2 stops
$334United Airlines
Tue, May 12 - Wed, May 13
United Airlines Logo
8:10 am - 9:24 pm
MSN
-
SJU
12h 14m
2 stops
United Airlines Logo
7:40 am - 3:00 pm
SJU
-
MSN
8h 20m
1 stop
$335United Airlines
Sun, Sep 6 - Wed, Sep 16
American Airlines Logo
12:52 pm - 10:56 pm
MSN
-
SJU
9h 04m
1 stop
American Airlines Logo
3:55 pm - 12:21 am
SJU
-
MSN
9h 26m
1 stop
$339American Airlines
Sat, Apr 25 - Sun, May 10
American Airlines Logo
7:10 am - 11:02 pm
MSN
-
SJU
14h 52m
1 stop
American Airlines Logo
11:59 pm - 11:05 am
SJU
-
MSN
12h 06m
1 stop
$350American Airlines
Sat, Apr 25 - Sun, May 10
American Airlines Logo
5:08 pm - 10:48 am
MSN
-
SJU
16h 40m
1 stop
American Airlines Logo
6:00 am - 11:28 pm
SJU
-
MSN
18h 28m
1 stop
$351American Airlines
Sat, Sep 5 - Sat, Sep 12
American Airlines Logo
8:26 pm - 12:31 pm
MSN
-
MBJ
16h 05m
1 stop
American Airlines Logo
12:43 pm - 11:23 pm
MBJ
-
MSN
10h 40m
1 stop
$352American Airlines
Wed, Apr 22 - Wed, Apr 29
American Airlines Logo
8:05 am - 8:51 pm
MSN
-
SJU
11h 46m
2 stops
American Airlines Logo
1:31 pm - 11:28 pm
SJU
-
MSN
10h 57m
2 stops
$355American Airlines
Sat, Apr 11 - Fri, Apr 17
British Airways Logo
5:08 pm - 1:21 pm
MSN
-
SXM
19h 13m
1 stop
British Airways Logo
2:24 pm - 11:55 pm
SXM
-
MSN
10h 31m
1 stop
$630British 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 April and March, when the average cost of round-trip tickets is $661 and $658 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 12% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$125
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 10% lower on average.
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 8302 reviews
8.5Crew
8.1Boarding
7.2Food
7.9Comfort
7.8Entertainment
Airline reviews

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

6.0 GoodCarl, Mar 2026
ATL - ATW
Read more Delta reviews

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

This was a Latam operated flight. Seats seemed a bit narrow in business class. Older aircraft.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

8 hours late and the plane smelled like urine, that smell in the morning when your child wet the bed in the night.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

Miserable. This entire round trip was miserable. I booked evening flights to and from Detroit on consecutive days that should have had me at my destination by 10:30. Instead I arrived after 3am on my flight to Detroit and after midnight on my return. Multiple unforced errors like awaiting bags to get put on the plane for almost an hour in Detroit and a 20 minute delay to pull up to the gate in Atlanta has me rethinking my assumption that delta is the best and most reliable airline

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Experience was great - no complaints. Took off on time, landed early. Got to the gate relatively quickly - took a little bit of extra time to deplane but nothing excessive.

Business class seats felt very cramped compared to other airlines.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

OK, we were delayed and had to de plane and reboard.

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Both my flight where delayed Had 25min to make it to my transfer flight

Everything was on time and service on the flight was great!

Wifi Bluetooth features for watching in flight movie was horrible. Screen kept blacking out no connection of sound although it said connected. Other than that smooth trip .

The 777’s economy seat’s legroom was more tolerable than expected. I appreciate the reclining mechanism which slides the seat forward to minimize cannibalizing the space behind. The food was terrible: very salty.

I rated the experience "mediocre" because of the 2 hour delay in take off. This is the 4th flight from DFW on AA where there was a delay and in one of the instances (after 13 delays), the flight was cancelled. I understand weather but for the March 18th flight, there was no weather issue in Dallas or Detroit. I called Concierge Key and they were wonderful, booking me on a later flight in case my flight was cancelled. I have flown with American for many years and never has there been this consistent pattern of delays. Very disappointing.

They put me on an earlier and I got home sooner

Not good. One of my luggage is missing. And until now they can’t find it

Horrible experience upon landing. Probably more due to DCA utter incompetence than AA.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

Really good. I accidentally left my duffel on the plane and the reps were so friendly in retrieving it.

My 9:50AM flight was delayed to 3:40PM "due to incoming aircraft delay". No aircraft is "delayed" that long. Found out once we did board (after several changes in times) that the aircraft had a maintenance issue and we had to wait for another aircraft. Just tell us that. The aircraft we did get was old and the seats need to be updated. I have been traveling for several weeks with AA and you should refresh your entertainment content as frequent flyers have gone through most of your new content. I have Celiac and a shellfish allergy and continue to have struggles with meals on business and first class flights. Please keep this in mind. Sorry - was a long travel day yesterday and a bit cranky this morning with my experience comments. Still an AA fan.

The business steward was absolutely amazing! Smiles and kindness! Wish all AA flights are like this one!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

Not really sure I enjoyed the flight at all. The flight attendants seemed a little tired and rude at times. The snacks were lacking in taste and sustenance. The flight was incredibly turbulent for three plus hours and the pilot had to do a second pass to land at our final destination because he was coming in so fast. He must have taken a short cut and because of it we had to suffer the violent turbulence and the dropping down. It had to be one of if not the worse flights I have ever been on and have traveled vastly all over the world.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports