$239 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 11/12. 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
$306
Overall average: $524
American Airlines
Tue 12/23Sun 1/11
SJU - MSN • 1 stop
Cheapest one-way
$200
Typical prices: $169-$233
Delta
Wed 11/12
SJU - MSN • 1 stop
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Flight Deals
Useful Info
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

Tue, Dec 23 - Sun, Jan 11
American Airlines Logo
6:00 am - 7:40 pmSJU-MSN
15h 40m1 stop
American Airlines Logo
6:00 am - 9:39 pmMSN-SJU
13h 39m1 stop
$306American Airlines
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Tue, Nov 18 - Thu, Jan 15
Delta Logo
7:15 am - 5:22 pmSJU-MSN
12h 07m2 stops
Delta Logo
11:00 am - 11:44 pmMSN-SJU
10h 44m2 stops
$317Delta
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Tue, Dec 23 - Sun, Jan 11
American Airlines Logo
6:00 am - 5:41 pmSJU-MSN
13h 41m1 stop
American Airlines Logo
6:00 am - 8:50 pmMSN-SJU
12h 50m2 stops
$339American Airlines
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Mon, Dec 22 - Sun, Jan 11
American Airlines Logo
1:30 am - 10:37 amSJU-MSN
11h 07m1 stop
American Airlines Logo
7:30 am - 9:39 pmMSN-SJU
12h 09m1 stop
$366American 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
6:53 pm - 12:35 pmMSN-SJU
16h 42m2 stops
$382American Airlines
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Thu, Nov 20 - Mon, Nov 24
United Airlines Logo
8:10 am - 2:54 pmSJU-MSN
8h 44m1 stop
United Airlines Logo
8:25 am - 10:22 pmMSN-SJU
11h 57m2 stops
$399United Airlines
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Mon, Dec 22 - Sun, Jan 11
American Airlines Logo
1:30 am - 10:37 amSJU-MSN
11h 07m1 stop
American Airlines Logo
6:00 am - 8:50 pmMSN-SJU
12h 50m2 stops
$400American Airlines
Find Deal
Thu, Dec 25 - Sat, Jan 3
United Airlines Logo
3:35 pm - 10:30 pmNAS-MSN
7h 55m1 stop
United Airlines Logo
10:45 am - 3:22 pmMSN-NAS
27h 37m1 stop
$436United Airlines
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Thu, Dec 25 - Sat, Jan 3
United Airlines Logo
1:05 pm - 4:45 pmNAS-MSN
28h 40m2 stops
United Airlines Logo
2:29 pm - 1:33 pmMSN-NAS
22h 04m2 stops
$471United Airlines
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Tue, Nov 18 - Thu, Jan 15
American Airlines Logo
7:15 am - 4:58 pmSJU-MSN
11h 43m1 stop
American Airlines Logo
11:29 am - 9:39 pmMSN-SJU
8h 10m1 stop
$472American Airlines
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Useful Info

Good to know

Low seasonFebruary
Cheapest flight$200
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly with an average 11% 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 11040 reviews
8.0Crew
6.4Food
7.5Boarding
6.9Entertainment
7.2Comfort
Airline reviews

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

10.0 Excellentchloe, Nov 2025ORD - ATW
Read more American Airlines reviews

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

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

The flight was smooth, the pilot kept us informed about delays and we arrived more of less on time

Flight delay was communicated before leaving for airport which caused it to be a non-event. Great flight and crew!

Did not get any refreshments. Crew was very nice but limited. Small seats

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Wish a flight with more than 2 hours with some snack rather than just cookie/biscuit.

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Nice comfortable flight from Barcelona back to the states. The premium economy offers the extra room we need for my husband. The food was good and our flight attendants were excellent.

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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)