$118 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 12/5. 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
$366
Overall average: $484
Frontier
Thu 11/13Sun 11/16
SJU - MSN • 2 stops
Cheapest one-way
$118
Typical prices: $135-$219
Delta
Fri 12/5
SJU - MSN • 1 stop
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Flight Deals
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Flight Deals

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

Thu, Nov 13 - Sun, Nov 16
Frontier Logo
2:11 am - 7:15 pmSJU-MSN
19h 04m2 stops
Frontier Logo
8:00 pm - 4:10 pmMSN-SJU
18h 10m2 stops
$366Frontier
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Thu, Mar 12 - Mon, Mar 16
American Airlines Logo
9:26 am - 9:27 pmSJU-MSN
13h 01m2 stops
American Airlines Logo
5:25 pm - 2:35 pmMSN-SJU
20h 10m2 stops
$382American Airlines
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Tue, Dec 16 - Tue, Dec 30
American Airlines Logo
5:56 pm - 11:40 pmSJU-MSN
7h 44m1 stop
American Airlines Logo
8:10 pm - 3:08 pmMSN-SJU
16h 58m1 stop
$407American Airlines
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Sat, Nov 15 - Thu, Jan 15
American Airlines Logo
3:43 pm - 11:26 pmSJU-MSN
9h 43m1 stop
American Airlines Logo
7:20 am - 9:39 pmMSN-SJU
12h 19m1 stop
$432American Airlines
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Thu, Mar 12 - Mon, Mar 16
American Airlines Logo
6:20 am - 2:02 pmSJU-MSN
8h 42m1 stop
American Airlines Logo
6:53 pm - 12:35 pmMSN-SJU
16h 42m2 stops
$435American Airlines
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Thu, Dec 25 - Sat, Jan 3
United Airlines Logo
4:25 pm - 10:57 pmNAS-MSN
7h 32m1 stop
United Airlines Logo
3:46 pm - 1:33 pmMSN-NAS
20h 47m2 stops
$436United Airlines
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Sat, Nov 15 - Thu, Jan 15
Delta Logo
7:15 am - 5:08 pmSJU-MSN
11h 53m2 stops
Delta Logo
11:15 am - 11:44 pmMSN-SJU
10h 29m1 stop
$477Delta
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Fri, Nov 14 - Sun, Nov 16
United Airlines Logo
8:30 am - 7:21 pmSJU-MSN
12h 51m2 stops
United Airlines Logo
10:35 am - 9:00 pmMSN-SJU
8h 25m1 stop
$489United Airlines
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Fri, Nov 14 - Thu, Jan 15
United Airlines Logo
2:05 am - 2:00 pmSJU-MSN
13h 55m2 stops
United Airlines Logo
6:30 am - 3:40 pmMSN-SJU
7h 10m1 stop
$512United Airlines
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Thu, Apr 23 - Sun, Apr 26
Delta Logo
1:50 pm - 10:35 pmSXM-MSN
9h 45m1 stop
Delta Logo
5:45 am - 2:09 pmMSN-SXM
7h 24m1 stop
$879Delta
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Useful Info

Good to know

Low seasonFebruary
Cheapest flight$118
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 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.

Reviews of the 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 11030 reviews
7.2Comfort
6.9Entertainment
8.0Crew
7.5Boarding
6.4Food
Airline reviews

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

10.0 ExcellentMax, Oct 2025DCA - SAV
Read more American Airlines reviews

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.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

Flight delayed and missed connection. Rescheduled flight cancelled after 6 hrs wait. Rerouted thru ORD, flight cancelled, overnight stay in ORD. Still in the air on new flight!

We are too tired and frustrated to comment politely at this point

Terrible. Our luggage was delayed and couldn’t be delivered for several days. We got bad information from the airline agents at baggage claim. We had to pick up our car so we wouldn’t be charged for an extra day. We got lost in the maze of airport parking. The baggage claim agents didn’t offer us any compensation for our extra time and expense. We are tired, hungry and very frustrated.

The flight was flawless and we even arrived between 20 and 25 minutes early!

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

Delayed delayed delayed and no offer for food or vouchers

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Everything you need to know for your flight to Madison

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Madison (MSN)

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