$113 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 4/21. 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 Cana2 stops$433
Santo Domingo
Santo Domingo2 stops$618
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$653
Nassau
Nassau1 stop$552
Simpson Bay
Simpson Bay2 stops$380
Providenciales
Providenciales2 stops$476
Bridgetown
Bridgetown2 stops$697
George Town
George Town2 stops$354
St. John's
St. John's2 stops$740
Aguadilla
Aguadilla1 stop$565
Punta Cana
Punta Cana2 stops$433
Santo Domingo
Santo Domingo2 stops$618
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$653
Nassau
Nassau1 stop$552
Simpson Bay
Simpson Bay2 stops$380
Providenciales
Providenciales2 stops$476
Bridgetown
Bridgetown2 stops$697
George Town
George Town2 stops$354
St. John's
St. John's2 stops$740
Aguadilla
Aguadilla1 stop$565

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

Sat, Apr 25 - Wed, Apr 29
American Airlines Logo
5:08 pm - 10:47 am
MSN
-
STT
16h 39m
1 stop
American Airlines Logo
11:27 am - 11:28 pm
STT
-
MSN
13h 01m
1 stop
$324American Airlines
Wed, Apr 22 - Wed, Apr 29
American Airlines Logo
6:45 am - 8:51 pm
MSN
-
SJU
13h 06m
1 stop
American Airlines Logo
7:25 am - 11:55 pm
SJU
-
MSN
17h 30m
1 stop
$331American Airlines
Mon, Apr 27 - Mon, May 4
American Airlines Logo
5:08 pm - 12:03 pm
MSN
-
SJU
17h 55m
1 stop
American Airlines Logo
11:59 pm - 11:05 am
SJU
-
MSN
12h 06m
1 stop
$338American 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
Tue, May 26 - Wed, Jun 3
Delta Logo
11:04 am - 8:30 pm
MSN
-
SJU
8h 26m
1 stop
Delta Logo
6:15 am - 9:27 pm
SJU
-
MSN
16h 12m
2 stops
$358Delta
Thu, Sep 24 - Wed, Oct 7
United Airlines Logo
6:45 am - 8:38 pm
MSN
-
SJU
12h 53m
2 stops
United Airlines Logo
3:56 pm - 12:12 am
SJU
-
MSN
9h 16m
1 stop
$369United Airlines
Tue, Apr 14 - Tue, Apr 21
Delta Logo
1:25 pm - 11:12 pm
MSN
-
SJU
8h 47m
2 stops
Delta Logo
6:15 am - 4:17 pm
SJU
-
MSN
11h 02m
1 stop
$380Delta
Wed, Jul 1 - Wed, Jul 8
United Airlines Logo
5:00 am - 3:10 pm
MSN
-
MBJ
10h 10m
2 stops
United Airlines Logo
2:40 pm - 9:59 am
MBJ
-
MSN
19h 19m
2 stops
$417United Airlines
Wed, May 20 - Sat, May 30
Multiple Airlines Logo
6:05 pm - 9:54 am
MSN
-
STT
14h 49m
1 stop
Multiple Airlines Logo
10:49 am - 8:25 am
STT
-
MSN
46h 36m
2 stops
$494Multiple Airlines
Wed, May 20 - Sat, May 30
Multiple Airlines Logo
6:05 pm - 9:54 am
MSN
-
STT
14h 49m
1 stop
Multiple Airlines Logo
10:49 am - 7:15 pm
STT
-
MSN
9h 26m
1 stop
$518Multiple 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 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$113
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 8356 reviews
7.8Entertainment
8.1Boarding
7.9Comfort
8.5Crew
7.2Food
Airline reviews

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

2.0 MediocreJames, Mar 2026
BOS - LGA
Read more Delta reviews

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

Excellent service, I love the soft blush pink mood lighting on the 767-400ER during meal service. The overhead gasper vents on the 767-400ER were also very strong with a lot of airflow to keep me comfortable on my flight.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

I took seat 15A in anticipation of window seat, there is no window.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Overall, the flight was good. Lounge access should be with all business class tickets.

They promise free wi-fi prior to boarding and then once on board you are informed you have to purchase wifi even after being a mileagePlus member.

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

Awful. No counter attendants. No dinner offered due to delays.

Horrible service no Wi-Fi connection on both leg of the flight and they are refusing to fix bad service

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Flights were on time. Free Wifi on plane. Everything was well organized.

During landing. 2 crew members passed 3 times by my lane and didn't notice that people in front of us had their site to the furthermore reclined... That was uncomfortable and could have been dangerous.

They delayed the flight from 9:00 to 11:55 At 11:45 they canceled the flight. I paid a premium price for the tickets with poor service

The flight changed gates multiple times and flight had to be delayed multiple times

We called Kayak for a change due to the TSA situation in Atlanta. What we got was a canceled return flight (in error) and we had to find the mistake. Not happy with Kayak who blamed it on AA.

Tv screens and movie selection v good. Friendly staff. They were really worried about max capacity and room for carryons. That is never fun but i had no problem finding space when I boarded.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Delayed for mechanical and no updates on what was happening and how long the delay might be.

My flight from LGA was cancelled and my rebooked flight from JFK was delayed numerous times. I will now be getting home after 2am.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

On the return flight, arriving in Denver we sat on the tarmac in Denver for over 20 minutes.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The flight attendant in business class was excellent! Professional, friendly and attentive.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports