$161 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 2/27. 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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Everything you should know

Cheapest round-trip
$295
Overall average: $582
American Airlines
Thu 1/29Sun 2/1
SJU - MSN • 1 stop
Cheapest one-way
$161
Typical prices: $194-$382
Delta
Fri 2/27
SJU - MSN • 1 stop
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Flight Deals
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Flight Deals

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

Thu, Jan 29 - Sun, Feb 1
American Airlines Logo
6:00 am - 4:52 pmSJU-MSN
12h 52m1 stop
American Airlines Logo
3:09 pm - 10:48 amMSN-SJU
17h 39m2 stops
$295American Airlines
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Wed, Jan 28 - Sun, Feb 1
United Airlines Logo
2:05 am - 2:52 pmSJU-MSN
14h 47m2 stops
United Airlines Logo
3:48 pm - 6:11 amMSN-SJU
12h 23m2 stops
$325United Airlines
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Wed, Jan 28 - Sun, Feb 1
United Airlines Logo
2:05 am - 12:03 pmSJU-MSN
11h 58m2 stops
United Airlines Logo
2:56 pm - 6:11 amMSN-SJU
13h 15m2 stops
$368United Airlines
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Sun, Dec 7 - Sun, Dec 14
American Airlines Logo
8:18 am - 11:49 pmSJU-MSN
17h 31m1 stop
American Airlines Logo
10:20 am - 11:52 pmMSN-SJU
11h 32m1 stop
$380American Airlines
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Thu, Dec 4 - Mon, Dec 8
American Airlines Logo
4:41 pm - 11:49 pmSJU-MSN
9h 08m1 stop
American Airlines Logo
6:13 am - 10:09 pmMSN-SJU
13h 56m2 stops
$399American Airlines
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Mon, Feb 23 - 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
$402United Airlines
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Sat, Dec 27 - Sat, Jan 3
American Airlines Logo
6:15 pm - 11:59 pmSJU-MSN
7h 44m1 stop
American Airlines Logo
8:10 pm - 5:00 amMSN-SJU
6h 50m1 stop
$406American Airlines
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Thu, Dec 4 - Sun, Dec 7
Delta Logo
3:38 pm - 12:50 pmMBJ-MSN
22h 12m2 stops
Delta Logo
5:38 am - 1:04 pmMSN-MBJ
6h 26m1 stop
$441Delta
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Tue, Dec 9 - Sat, Dec 13
Delta Logo
2:55 pm - 10:26 pmNAS-MSN
8h 31m1 stop
Delta Logo
5:38 am - 1:30 pmMSN-NAS
6h 52m1 stop
$445Delta
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Tue, Dec 9 - Sat, Dec 13
Delta Logo
5:08 pm - 12:50 pmNAS-MSN
20h 42m2 stops
Delta Logo
5:38 am - 1:30 pmMSN-NAS
6h 52m1 stop
$449Delta
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Useful Info

Good to know

Low seasonFebruary
Cheapest flight$161
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly with an average 9% 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 11047 reviews
6.4Food
7.2Comfort
8.0Crew
6.9Entertainment
7.5Boarding
Airline reviews

We were told the flight was delayed 5 times, then it was moved to the next day.

2.0 MediocreAnonymous, Nov 2025DCA - LAX
Read more American Airlines reviews

We were told the flight was delayed 5 times, then it was moved to the next day.

More choices on snacks. Built-in video screen to enjoy entertainment choices.

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.

flight was good until we arrived at cmh ten minutes early but then sat on tarmac for twenty minutes because a plane was at our gate, so we had to wait despite the pilot tellling us 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.

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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)