$118 Find Cheap Flights from Caribbean 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 12/9. 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 Caribbean to Madison

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

Tue, Nov 11 - Fri, Nov 14
American Airlines Logo
6:00 am - 2:57 pmSJU-MSN
10h 57m2 stops
American Airlines Logo
8:12 pm - 2:53 pmMSN-SJU
16h 41m1 stop
$361American Airlines
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Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
8:35 am - 3:02 pmSJU-MSN
8h 27m1 stop
United Airlines Logo
2:48 pm - 6:11 amMSN-SJU
13h 23m2 stops
$368United Airlines
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Tue, Feb 24 - Sat, Feb 28
American Airlines Logo
7:20 am - 2:05 pmSJU-MSN
8h 45m1 stop
American Airlines Logo
3:26 pm - 4:55 amMSN-SJU
11h 29m1 stop
$399American Airlines
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Tue, Nov 11 - Fri, Nov 14
American Airlines Logo
6:00 am - 2:57 pmSJU-MSN
10h 57m2 stops
American Airlines Logo
6:00 am - 8:48 pmMSN-SJU
12h 48m2 stops
$420American Airlines
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Thu, Mar 12 - Mon, Mar 16
American Airlines Logo
3:45 pm - 10:35 amSJU-MSN
19h 50m2 stops
American Airlines Logo
3:52 pm - 10:55 amMSN-SJU
18h 03m2 stops
$435American Airlines
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Thu, Mar 12 - Mon, Mar 16
American Airlines Logo
5:35 am - 5:14 pmSJU-MSN
12h 39m1 stop
American Airlines Logo
4:22 pm - 10:55 amMSN-SJU
17h 33m2 stops
$480American Airlines
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Mon, Feb 23 - Sat, Feb 28
United Airlines Logo
2:05 am - 2:07 pmSJU-MSN
14h 02m2 stops
United Airlines Logo
2:48 pm - 6:11 amMSN-SJU
13h 23m2 stops
$483United Airlines
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Mon, Nov 10 - Fri, Nov 14
United Airlines Logo
2:05 am - 2:03 pmSJU-MSN
13h 58m2 stops
United Airlines Logo
6:30 am - 3:40 pmMSN-SJU
7h 10m1 stop
$504United Airlines
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Fri, Mar 6 - Tue, Mar 10
United Airlines Logo
3:35 pm - 10:38 pmNAS-MSN
8h 03m1 stop
United Airlines Logo
6:00 am - 2:32 pmMSN-NAS
7h 32m1 stop
$515United Airlines
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Tue, Dec 30 - Wed, Jan 7
Multiple Airlines Logo
2:59 am - 5:28 pmSJU-MSN
16h 29m1 stop
Multiple Airlines Logo
6:16 pm - 9:52 amMSN-SJU
13h 36m1 stop
$557Multiple Airlines
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Everything you should know

Cheapest round-trip
$361
Overall average: $376
American Airlines
Tue 11/11Fri 11/14
SJU - MSN • 2 stops
Cheapest one-way
$118
Typical prices: $135-$219
Delta
Tue 12/9
SJU - MSN • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Madison!
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$118
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly with an average 8% increase in price.
Flight from San Juan to Madison

FAQs for booking flights from Caribbean to Madison

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Madison from 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 Caribbean 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 with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean 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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Caribbean to Madison

 
Need help choosing which airline to fly with from Caribbean 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 11028 reviews
6.9Entertainment
6.4Food
7.2Comfort
8.0Crew
7.5Boarding
Airline reviews

The only thing to like was that we eventually got to our destination

2.0 MediocrePaul T., Oct 2025DFW - ATL
Read more American Airlines reviews

The only thing to like was that we eventually got to our destination

Delayed delayed delayed and no offer for food or vouchers

Typically flights with AA are good. The staff are pleasant, welcoming, and efficient.

A couple ladies from the crew were so rude and nasty. Thought they were mad at having to be there especially if you asked a question. This will make me think twice next time if I book a flight with you.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

Poor seat in rear of aircraft Food at Admiral’s Club Terminal D at DFW inedible

Always seated jammed in rear of aircraft Admirals Club food at DFW terminal D was absolute worst food experience and I pay $600/year to eat this dried out junk

Flight was delayed because of a bird strike. They had another plane available within 45 minutes.

The business class seats are dated and uncomfortable. The space is bare minimum and there is absolutely no privacy. For $4K, this is not what I expect.

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

Traveling to a place near Madison?

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Everything you need to know for your flight to Madison

Information on the airport you'll fly into in Madison

Madison (MSN)

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