$213 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 12/23. 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$366
Santo Domingo
Santo Domingo2 stops$557
Montego Bay
Montego Bay1 stop$473
Oranjestad
Oranjestad1 stop$586
Nassau
Nassau1 stop$445
Simpson Bay
Simpson Bay2 stops$592
Providenciales
Providenciales1 stop$380
Port of Spain
Port of Spain2 stops$793
Bridgetown
Bridgetown2 stops$606
George Town
George Town1 stop$470
St. John's
St. John's2 stops$604
Aguadilla
Aguadilla2 stops$462
Punta Cana
Punta Cana2 stops$366
Santo Domingo
Santo Domingo2 stops$557
Montego Bay
Montego Bay1 stop$473
Oranjestad
Oranjestad1 stop$586
Nassau
Nassau1 stop$445
Simpson Bay
Simpson Bay2 stops$592
Providenciales
Providenciales1 stop$380
Port of Spain
Port of Spain2 stops$793
Bridgetown
Bridgetown2 stops$606
George Town
George Town1 stop$470
St. John's
St. John's2 stops$604
Aguadilla
Aguadilla2 stops$462

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 - Wed, Jan 28
Delta Logo
11:00 am - 11:44 pmMSN-SJU
10h 44m2 stops
Delta Logo
7:30 am - 4:19 pmSJU-MSN
10h 49m1 stop
$235Delta
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Thu, Jan 29 - Tue, Feb 3
American Airlines Logo
11:29 am - 9:39 pmMSN-SJU
8h 10m1 stop
American Airlines Logo
6:00 am - 12:46 pmSJU-MSN
8h 46m1 stop
$268American Airlines
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Tue, Feb 24 - Wed, Mar 4
Delta Logo
11:20 am - 8:30 pmMSN-SJU
7h 10m1 stop
Delta Logo
6:15 am - 4:19 pmSJU-MSN
12h 04m1 stop
$278Delta
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Sat, Jan 31 - Thu, Feb 5
American Airlines Logo
11:23 am - 11:59 pmMSN-SJU
10h 36m2 stops
American Airlines Logo
6:00 am - 3:27 pmSJU-MSN
11h 27m2 stops
$298American Airlines
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Tue, Feb 24 - Wed, Mar 4
American Airlines Logo
8:00 am - 8:36 pmMSN-SJU
10h 36m2 stops
American Airlines Logo
9:25 am - 4:42 pmSJU-MSN
9h 17m1 stop
$301American Airlines
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Tue, Mar 3 - Wed, Mar 11
Delta Logo
7:00 am - 11:49 pmMSN-SJU
14h 49m2 stops
Delta Logo
6:15 am - 4:38 pmSJU-MSN
11h 23m1 stop
$321Delta
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Tue, Jan 20 - Wed, Jan 28
United Airlines Logo
12:38 pm - 12:36 amMSN-SJU
9h 58m2 stops
United Airlines Logo
7:45 am - 5:47 pmSJU-MSN
12h 02m2 stops
$325United Airlines
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Tue, Dec 9 - Tue, Dec 16
American Airlines Logo
12:18 pm - 10:09 pmMSN-SJU
7h 51m1 stop
American Airlines Logo
7:00 am - 4:55 pmSJU-MSN
11h 55m1 stop
$331American Airlines
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Tue, Jan 20 - Tue, Jan 27
United Airlines Logo
10:45 am - 9:00 pmMSN-SJU
8h 15m1 stop
United Airlines Logo
2:05 am - 12:03 pmSJU-MSN
11h 58m2 stops
$333United Airlines
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Thu, Jan 15 - Mon, Jan 19
Copa Airlines Logo
8:15 am - 11:32 amMSN-SDQ
25h 17m2 stops
Copa Airlines Logo
7:05 pm - 7:07 pmSDQ-MSN
26h 02m2 stops
$612Copa Airlines
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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 $661 and $638 respectively.

What’s the cheapest day of the week to fly from Madison to Caribbean?

The average price of all round-trip flights from Madison to Caribbean clicked on KAYAK for each day over the last 12 months.

For Madison to Caribbean, Monday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Caribbean back to Madison, the best deals are generally found on Tuesday, with Saturday being the most expensive.

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$213
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Madison to Montego Bay

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 8009 reviews
7.9Entertainment
8.5Crew
7.9Comfort
8.1Boarding
7.3Food
Airline reviews

Plenty of leg room, temperature was great and staff was excellent. Would do it more often.

10.0 ExcellentJacky, Nov 2025JFK - LHR
Read more Delta reviews

Plenty of leg room, temperature was great and staff was excellent. Would do it more often.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

Older aircraft, no meal, only food was for purchase. Not impressed United.

United needs to step up their game. Delayed flight leaving Seattle, San Francisco. Older aircraft, not very comfortable.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Not pleasant trip cross country when the entertainment and WiFi system not working. No entertainment for entirety of route. Staff was rather nonchalant in that they dismissed the problem due to age of plane. It would have been nice to know this up front so I could have come prepared to read or download movies before boarding Coincidentally or not, there was a similar issue with the entertainment system on my previous flight I took on my fist leg of the trip. There are no seat TVs, so you must rely on the app when it works. United can do better. Also, what use it it to pay for boarding group 2 when half of the passengers are in the same line as you?

Plane boarded early a quickly, was mostly full. We left close to on time. And landed early.

My experience on this United Airlines flight was highly uncomfortable, primarily due to two issues: Cabin Temperature: The temperature on the Boeing 737 MAX 8 was unacceptably high, feeling consistently around 80 degrees throughout the flight. This made sleeping impossible and significantly detracted from the experience. Seating Arrangement: Being stuck in a middle seat for a six-and-a-half-hour overnight flight compounded the discomfort. Moving forward, I will always purchase a seat assignment to avoid this situation.

Premium Plus is a really good idea for longer flights

we landed at cmh ten minutes early but had to sit on tarmac for twenty minutes because a plane was at our gate despite the fact that 3 other gates were open.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so did have any food

I have a gluten allergy so didn't have any food

Loved the crew . Absolutely no complaints. Except for luggage lost

Everything was good The connects, with no blame to crew. Or pilots. I understand they are short staffed. Everything went well for me. I'll be using you guys again in May if not sooner.

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

We were very rushed by a staff member at the gate when transferring from American Airlines to Fijian. Then the plane stayed put for ages anyhow! The plane was delayed and my bag sent to San Francisco instead of Fiji

Baggage handling poor. Second time this has happened. My bag went to San Francisco instead of Fiji. No apology. Luckily Nadi airport staff are fantastic. My bag arrived in Fiji the next day.

We loved the steward on the plane. He made the night enjoyable

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports