$113 Find Cheap Flights from Caribbean Islands to Madison

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Madison departing on 10/7. 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

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Cheap Flights from Caribbean Islands to Madison

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean Islands to Madison 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 Caribbean Islands to Madison

Fri, Jul 4 - Tue, Jul 8
American Airlines Logo
6:05 am - 4:21 pmSJU-MSN
11h 16m2 stops
American Airlines Logo
2:09 pm - 10:50 pmMSN-SJU
7h 41m1 stop
$387American Airlines
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Thu, Oct 30 - Mon, Dec 1
American Airlines Logo
3:05 pm - 10:00 amMBJ-MSN
18h 55m2 stops
American Airlines Logo
6:26 am - 2:48 pmMSN-MBJ
7h 22m1 stop
$409American Airlines
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Thu, Oct 30 - Mon, Dec 1
American Airlines Logo
2:20 pm - 10:00 amMBJ-MSN
19h 40m1 stop
American Airlines Logo
6:26 am - 2:48 pmMSN-MBJ
7h 22m1 stop
$410American Airlines
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Thu, Oct 30 - Mon, Dec 1
American Airlines Logo
4:25 pm - 10:00 amMBJ-MSN
17h 35m2 stops
American Airlines Logo
6:48 pm - 11:50 amMSN-MBJ
16h 02m2 stops
$458American Airlines
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Fri, Jul 4 - Tue, Jul 8
American Airlines Logo
6:05 am - 4:21 pmSJU-MSN
11h 16m2 stops
American Airlines Logo
12:59 pm - 12:27 amMSN-SJU
10h 28m2 stops
$462American Airlines
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Thu, Jul 3 - Tue, Jul 8
American Airlines Logo
12:59 am - 7:12 pmSJU-MSN
19h 13m1 stop
American Airlines Logo
6:27 am - 10:50 pmMSN-SJU
15h 23m1 stop
$504American Airlines
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Sun, Aug 10 - Sun, Aug 31
United Airlines Logo
7:00 am - 8:58 pmSJU-MSN
14h 58m2 stops
United Airlines Logo
6:30 am - 2:44 pmMSN-SJU
7h 14m1 stop
$667United Airlines
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Tue, Jul 15 - Sun, Jul 20
United Airlines Logo
1:10 am - 1:54 pmSJU-MSN
13h 44m2 stops
United Airlines Logo
6:40 am - 11:54 pmMSN-SJU
16h 14m1 stop
$712United Airlines
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Tue, Jul 15 - Sun, Jul 20
United Airlines Logo
1:10 am - 11:43 amSJU-MSN
11h 33m2 stops
United Airlines Logo
6:40 am - 2:44 pmMSN-SJU
7h 04m1 stop
$720United Airlines
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Sat, Jul 19 - Fri, Jul 25
Delta Logo
2:36 pm - 11:27 pmSJU-MSN
9h 51m2 stops
Delta Logo
6:45 am - 8:39 pmMSN-SJU
12h 54m2 stops
$904Delta
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Good to know

Low seasonFebruary
High seasonDecember
Cheapest flight$113
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from San Juan to Madison

FAQs for booking flights from Caribbean Islands to Madison

  • How does KAYAK find such low prices on flights from Caribbean Islands to Madison?

    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 Caribbean Islands to Madison.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean Islands to Madison?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Madison from Caribbean Islands 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 Caribbean Islands to Madison?

    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 to Madison with an airline and back to Caribbean Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands to Madison?

    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 to Madison from Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top airline flying from Caribbean Islands to Madison

 
Need help choosing which airline to fly with from Caribbean Islands to Madison? 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.
7.2
American AirlinesOverall score based on 10000 reviews
8.0Crew
7.2Comfort
6.9Entertainment
7.5Boarding
6.5Food
Airline reviews

Loved the staff, boarding and drink options! Wish the comfort of the seat could have been better nevertheless

8.0 ExcellentVictor, Jun 2025AUS - LAX
Read more American Airlines reviews

Loved the staff, boarding and drink options! Wish the comfort of the seat could have been better nevertheless

The flight crew were friendly and attentive. Food was good and they passed out ice cream and drinks awhile after Lunch was done. The ice cream was a nice treat! I found several movies to watch during the flight. There was many movies and tv shows to choose from. We flew Premium economy and there was enough leg room to be comfortable. The seats were also comfortable. I would fly AA again if the airfare isn’t expensive.

The chair cushions may need an upgrade. I have been noticing they are so worn out, thin so you’d sit in a dip 😄. Other than that, all was an enjoyable trip. Thanks AA!

I’m impressed that we were on time in Sacramento after having a late departure in Newark and our made it. The staff was friendly and warm.

Cramped seats. FAA should make airlines have more legroom, for even short people complain

5.5 hour delay with no explanation on why, along with no proactive effort to reaccomodate me.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Everything you need to know for your flight to Madison

Information on the airport you'll fly into in Madison

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