$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 Cana2 stops$419
Santo Domingo
Santo Domingo2 stops$580
Montego Bay
Montego Bay1 stop$312
Oranjestad
Oranjestad1 stop$582
Nassau
Nassau2 stops$546
Simpson Bay
Simpson Bay2 stops$503
Providenciales
Providenciales1 stop$439
Port of Spain
Port of Spain2 stops$610
Bridgetown
Bridgetown1 stop$657
George Town
George Town1 stop$445
St. John's
St. John's2 stops$735
Aguadilla
Aguadilla1 stop$356
Punta Cana
Punta Cana2 stops$419
Santo Domingo
Santo Domingo2 stops$580
Montego Bay
Montego Bay1 stop$312
Oranjestad
Oranjestad1 stop$582
Nassau
Nassau2 stops$546
Simpson Bay
Simpson Bay2 stops$503
Providenciales
Providenciales1 stop$439
Port of Spain
Port of Spain2 stops$610
Bridgetown
Bridgetown1 stop$657
George Town
George Town1 stop$445
St. John's
St. John's2 stops$735
Aguadilla
Aguadilla1 stop$356

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, May 9 - Sat, May 16
American Airlines Logo
8:24 pm - 12:13 pm
MSN
-
MBJ
15h 49m
1 stop
American Airlines Logo
3:20 pm - 11:28 pm
MBJ
-
MSN
8h 08m
1 stop
$312American Airlines
Sat, May 9 - Sat, May 16
American Airlines Logo
8:24 pm - 12:13 pm
MSN
-
MBJ
15h 49m
1 stop
American Airlines Logo
3:20 pm - 11:28 pm
MBJ
-
MSN
8h 08m
1 stop
$317American Airlines
Thu, May 14 - Fri, May 22
United Airlines Logo
8:40 pm - 1:30 pm
MSN
-
MBJ
16h 50m
2 stops
United Airlines Logo
12:52 pm - 8:55 am
MBJ
-
MSN
20h 03m
2 stops
$322United Airlines
Fri, Apr 10 - Fri, Apr 17
American Airlines Logo
8:24 pm - 12:13 pm
MSN
-
MBJ
15h 49m
1 stop
American Airlines Logo
4:37 pm - 10:55 am
MBJ
-
MSN
18h 18m
2 stops
$326American Airlines
Tue, Mar 24 - Tue, Mar 31
United Airlines Logo
6:30 am - 12:46 pm
MSN
-
MBJ
6h 16m
1 stop
United Airlines Logo
4:12 pm - 10:07 am
MBJ
-
MSN
17h 55m
2 stops
$329United Airlines
Tue, Apr 7 - 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
$346Delta
Tue, Mar 10 - Tue, Mar 17
Delta Logo
6:00 am - 2:50 pm
MSN
-
PUJ
7h 50m
1 stop
Delta Logo
2:30 pm - 10:58 pm
PUJ
-
MSN
9h 28m
1 stop
$475Delta
Sat, Apr 25 - Sat, May 2
Multiple Airlines Logo
6:36 pm - 4:25 pm
MSN
-
NAS
20h 49m
1 stop
Multiple Airlines Logo
12:00 pm - 5:56 pm
NAS
-
MSN
6h 56m
1 stop
$583Multiple Airlines
Sat, Mar 28 - Sat, Apr 4
JetBlue Logo
5:30 am - 2:26 pm
MSN
-
SDQ
7h 56m
1 stop
JetBlue Logo
2:37 pm - 10:34 pm
SDQ
-
MSN
8h 57m
1 stop
$730JetBlue
Sat, Mar 21 - Sat, Mar 28
Multiple Airlines Logo
6:36 pm - 1:15 pm
MSN
-
SDQ
17h 39m
2 stops
Multiple Airlines Logo
10:56 am - 5:56 pm
SDQ
-
MSN
8h 00m
1 stop
$926Multiple 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 $660 and $623 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 with an average 5% 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 8237 reviews
7.9Comfort
7.8Entertainment
8.1Boarding
8.5Crew
7.2Food
Airline reviews

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

10.0 ExcellentBob, Feb 2026
FLL - MSP
Read more Delta reviews

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Flight was delayed due to crew being not on time

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

Never got on it. Was re-routed through Detroit and am still in airports 12 hours later waiting for my connecting plane to arrive.

Delta has too many delays now days. It is 1:06 am now. I was supposed to land in Norfolk at 10:30 pm. I got re-booked through Detroit and I’m still in Detroit. I hope to be landed in Norfolk by 3am. I’ve been in airports for 12 hours as of right now. There is a weather delay now but most delays lately have been maintenance.

We got delayed three hours and nobody thought to have the bathroom fixed while we were sitting waiting to board? took a full hour to have maintenance come and check it off. Had to shut the bathroom down twice so that the pilots could go to the bathroom. Everyone missed their connections.

Flight left on time and we arrived 25 minutes early! There was a gate available when we arrived so early on a busy Sunday afternoon! Flight attendants came around twice with the drinks cart.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Flight on time. Excellent service in Premium Economy. Great food served and cleaned up promptly. Unfortunately the climate control was malfunctioning and it was very cold and felt a bit like camping. Cold helps with sleep though so not complaining too much. Slept well. It asks to rate "entertainment". I do not like any IFE, don't shove a big screen in my face—I have my own phone if I want it. So this will always get low ratings.

We had turbulence ever 1/2 hr or so and the captains announcements were SOOOO LOUD

Everything was great except for the boarding process. Everyone is lining up all at the same time and it’s hard to tell between the groups as they are way too large.

Women boarding passengers at the gate was absolutely rude and disrespectful of passengers. The flight attendant was absolutely delightful! Smiling and connected with the passengers. So happy. The seats are cramped and uncomfortable but I guess that’s just the way it is Communication regarding flight was excellent

Overall we had a good experience during our flight from San Francisco to Houston.

Airport terminal was outdated, flight was on a small jet with no wifi

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Arrived early picked up my bag in a few minutes- great trip - thank you

Flight boarded, departed and landed on time. Excellent service from flight attendant in FIRST

Boarding is always an ordeal. Less dogs on flights. I am highly allergic to dogs and cats. Why are there so many animals these days?

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

Massimo, flight attendant was very authentic, attentive - wonderful. Food/wrap was just okay.

Worst experience ever. Flight could not land in Charlotte for what we were told was a ground stop. Had to be diverted to Raleigh to refuel. Strangely during ground stop, our connecting flight had no issue taking off on time causing us to miss our flight. We were told there were no other flights that day to our final destination and that two days out was the next one. The only flights to get us there were from Chicago the next morning. Completely opposite direction but it was a direct flight. So we get flown to Chicago and have to find a hotel in our own dime. The flight in the morning was also delayed. Thankfully only a short time. The non too of all this, our luggage did not arrive by the time we were there. Communication was terrible, through the entire trip. Complete incompetence. Will never fly American again.

Horrible. Got delayed many hours because their pilot wasn't trained for night landing at the airport and a rain delay made it a night landing. We have to wait hours for a qualified crew. They give us 12 dollar meal vouchers but most everything in the airport was closed and definitely more expensive than the vouchers.

I am an AA flyer for a very long time... AA has yet to disappoint.

Flight was delayed. Not much information on when the flight would take off. Eventually we were told it was maintenance. App was not giving updates.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports