$133 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 4/8. 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$449
Santo Domingo
Santo Domingo1 stop$673
Montego Bay
Montego Bay2 stops$323
Oranjestad
Oranjestad1 stop$549
Nassau
Nassau1 stop$514
Simpson Bay
Simpson Bay2 stops$586
Providenciales
Providenciales1 stop$363
Bridgetown
Bridgetown2 stops$672
George Town
George Town1 stop$468
St. John's
St. John's2 stops$660
Aguadilla
Aguadilla2 stops$796
Punta Cana
Punta Cana1 stop$449
Santo Domingo
Santo Domingo1 stop$673
Montego Bay
Montego Bay2 stops$323
Oranjestad
Oranjestad1 stop$549
Nassau
Nassau1 stop$514
Simpson Bay
Simpson Bay2 stops$586
Providenciales
Providenciales1 stop$363
Bridgetown
Bridgetown2 stops$672
George Town
George Town1 stop$468
St. John's
St. John's2 stops$660
Aguadilla
Aguadilla2 stops$796

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

Wed, Mar 18 - Tue, Mar 24
American Airlines Logo
5:17 pm - 12:27 pm
MSN
-
MBJ
19h 10m
2 stops
American Airlines Logo
1:27 pm - 9:08 am
MBJ
-
MSN
19h 41m
2 stops
$323American Airlines
Wed, Mar 18 - Tue, Mar 24
American Airlines Logo
5:17 pm - 9:07 am
MSN
-
MBJ
15h 50m
2 stops
American Airlines Logo
1:14 pm - 9:08 am
MBJ
-
MSN
19h 54m
1 stop
$328American Airlines
Tue, Apr 14 - Tue, Apr 21
American Airlines Logo
6:20 am - 6:10 pm
MSN
-
SJU
10h 50m
2 stops
American Airlines Logo
5:45 am - 3:42 pm
SJU
-
MSN
10h 57m
2 stops
$329American Airlines
Sat, Mar 7 - Fri, Mar 13
Frontier Logo
6:50 pm - 10:45 pm
MSN
-
SJU
25h 55m
1 stop
Frontier Logo
3:19 pm - 5:27 pm
SJU
-
MSN
27h 08m
1 stop
$336Frontier
Wed, Apr 8 - Wed, Apr 15
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
$340Delta
Sat, Apr 11 - Fri, Apr 17
United Airlines Logo
10:05 am - 9:24 pm
MSN
-
SJU
10h 19m
2 stops
United Airlines Logo
3:56 pm - 11:49 pm
SJU
-
MSN
8h 53m
1 stop
$399United Airlines
Tue, Mar 17 - Wed, Mar 25
Delta Logo
1:24 pm - 11:59 pm
MSN
-
SJU
9h 35m
2 stops
Delta Logo
3:30 pm - 10:58 pm
SJU
-
MSN
8h 28m
1 stop
$414Delta
Wed, Mar 18 - Tue, Mar 24
United Airlines Logo
6:30 am - 12:46 pm
MSN
-
MBJ
6h 16m
1 stop
United Airlines Logo
1:48 pm - 10:32 pm
MBJ
-
MSN
8h 44m
1 stop
$434United Airlines
Wed, Mar 4 - Tue, Mar 10
Multiple Airlines Logo
6:36 pm - 2:31 pm
MSN
-
STT
17h 55m
1 stop
Multiple Airlines Logo
2:36 pm - 5:56 pm
STT
-
MSN
28h 20m
1 stop
$530Multiple Airlines
Sat, Aug 1 - Fri, Aug 7
Multiple Airlines Logo
7:55 pm - 2:06 pm
MSN
-
STT
17h 11m
1 stop
Multiple Airlines Logo
3:12 pm - 7:15 pm
STT
-
MSN
29h 03m
1 stop
$621Multiple 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 $640 and $622 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 10% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$133
Best time to beat the crowds but there is an average 7% increase 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 8204 reviews
7.8Entertainment
8.5Crew
7.2Food
8.1Boarding
7.9Comfort
Airline reviews

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

10.0 ExcellentSoosnata, Feb 2026
LAX - HNL
Read more Delta reviews

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Good experience and the flight landed early. There was no food I had or entertainment.

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

Flight was delayed. No information on why it was delayed. After we boarded the flight, , the crew made announcement that the captain hs not arrived and he will take 15 mins more to arrive. Passengers were just sitting patiently for the captain to arrive and start, Terrible experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Smallest leg room I've ever had on a plane.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Excellent!!! Aeromexico is a great airline. What was not that good is the service provided by Kayak. It is never clear and not easy to manage.

Entertainment kept turning itself off. Gave up on watching a movie.

Both the WIFI and entertainment did not work for 2.5h

The crew made our experience extremely bad. They were rude and didn’t have anything for kids.

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Very disappointing given gate agent behavior. Filed a formal complaint with United.

Do not like the size of the overhead bin. I think staff should monitor the size of suitcases that are being carried on by passengers to ensure they meet the size requirement.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Flight delayed. WiFi connectivity very poor if not existant. Last minute arrival forced me to run to catch my connection.

Both of my flights arrived early and check in process was smooth

Overall it was a good flight. Because we traveled on a Saturday we were upgraded to FC since my wife and I are both Executive Platinum. The only areas for improvement we noted are better snack assortment and perhaps a little nicer plane as American is flying some older planes now. Everything else on this flight was excellent, which is frankly not the norm for American since we have had multiple issues on prior AA flights.

The smell from the bathroom kept wafting through the cabin. It made people sick.

The flight was really crowded. Flight attendants were just ok.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Didn't get a seat assignment until the last minute even though i picked a seat.

American has been able to implement an algorithm that makes it possible for nearly every one of my evening flights to be late. Congratulations!

I was on a small regional flight from Detroit to Philadelphia. When we landed the outside cruise needed to turn something off with the engine, which took quite a long time. Then, when they allowed us to get off the plane it was outside. They took their time, unloading all the luggage and waited till they unloaded all the luggage before they brought it over to us. It was 9 o’clock at night freezing cold out, and there was no proactive hustle to try to get people their luggage. It was really one of the worst experiences I think I’ve ever had with American until a manager came over. I don’t think they were going to even consider pulling the luggage over to the people that had been waiting outside for at least 10 minutes in the freezing cold.

The flight was fine, once we got underway. It was more than hour delayed

Beverage service was not good. Also just one service in 5 hr 30 min flight. No ask fir water ir anything beside one time beverage service.

Waited for oxygen tanks for 30 minutes after boarding was complete.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports