$183 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 11/7. 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

Tue, Dec 16 - Tue, Jan 13
American Airlines Logo
12:45 pm - 9:09 pmSJU-MSN
10h 24m2 stops
American Airlines Logo
11:43 am - 11:40 pmMSN-SJU
9h 57m1 stop
$255American Airlines
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Fri, Sep 19 - Sun, Sep 21
American Airlines Logo
4:43 pm - 9:05 amSJU-MSN
17h 22m2 stops
American Airlines Logo
6:40 pm - 12:47 pmMSN-SJU
17h 07m2 stops
$260American Airlines
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Tue, Dec 16 - Tue, Jan 13
American Airlines Logo
2:30 pm - 11:41 pmSJU-MSN
11h 11m1 stop
American Airlines Logo
11:43 am - 11:40 pmMSN-SJU
9h 57m1 stop
$295American Airlines
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Sat, Nov 8 - Tue, Nov 11
American Airlines Logo
6:42 pm - 11:58 pmSJU-MSN
7h 16m1 stop
American Airlines Logo
6:33 am - 5:05 pmMSN-SJU
8h 32m1 stop
$301American Airlines
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Fri, Aug 29 - Sun, Aug 31
American Airlines Logo
8:00 am - 11:48 pmSJU-MSN
16h 48m1 stop
American Airlines Logo
5:30 am - 2:05 pmMSN-SJU
7h 35m1 stop
$303American Airlines
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Wed, Sep 24 - Mon, Sep 29
American Airlines Logo
4:43 pm - 9:59 amSJU-MSN
18h 16m2 stops
American Airlines Logo
7:30 am - 3:52 pmMSN-SJU
7h 22m1 stop
$335American Airlines
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Fri, Nov 7 - Tue, Nov 11
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
$380United Airlines
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Mon, Dec 15 - Tue, Jan 13
United Airlines Logo
2:05 am - 2:01 pmSJU-MSN
13h 56m2 stops
United Airlines Logo
10:45 am - 9:00 pmMSN-SJU
8h 15m1 stop
$385United Airlines
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Mon, Dec 22 - Tue, Jan 13
Delta Logo
3:13 am - 1:52 pmSJU-MSN
12h 39m2 stops
Delta Logo
9:26 am - 11:49 pmMSN-SJU
12h 23m2 stops
$565Delta
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Fri, Sep 19 - Sun, Sep 21
Logo
12:06 pm - 5:28 pmSJU-MSN
30h 22m2 stops
Logo
7:59 pm - 2:34 amMSN-SJU
29h 35m3 stops
$703
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Useful Info

Good to know

Low seasonFebruary
Cheapest flight$183
Best time to beat the crowds with an average 4% drop 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 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 10000 reviews
8.0Crew
7.5Boarding
6.9Entertainment
7.2Comfort
6.5Food
Airline reviews

Pathetic check in experience once again. Not enough staff scheduled at bag drop or for special assistance at LHR. Really need to rethink the whole self check in procedure. The crew was good. A very decent selection of special meals in this leg as compared to the JFK-LHR leg.

6.0 GoodA, Jul 2025LHR - JFK
Read more American Airlines reviews

Pathetic check in experience once again. Not enough staff scheduled at bag drop or for special assistance at LHR. Really need to rethink the whole self check in procedure. The crew was good. A very decent selection of special meals in this leg as compared to the JFK-LHR leg.

We had to turn around and head back to Manchester. Problem with a plane engine.

Flight was delayed. Staff at the gate effectively and proactively communicated about the delay.

Very poor delay in dfw was really bad n long

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Very clean and comfortable cabin. Amazing Mediterranean salad for lunch before landing. Great range of films to watch. Really quiet and easy to sleep on the flight also. The initial food was a bit weird: odd fried chicken pieces in some weird white gloop, but that would be my lack of cultural knowledge on the grub. Salad more than made up for it at the other end. Staff were super attentive and helpful. Great and easy flight

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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