$144 Find Cheap Flights from Caribbean to Madison - Compare and Save

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 10/30. 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

Sat, Sep 5 - Sat, Sep 12
Multiple Airlines Logo
12:11 pm - 7:15 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
8h 04m1 stop Orlando
Multiple Airlines Logo
10:33 am - 1:34 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
26h 01m2 stops Tampa Fort Lauderdale
$335Multiple Airlines
Fri, Sep 4 - Sat, Sep 12
Multiple Airlines Logo
5:37 pm - 9:47 amSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
17h 10m1 stop Tampa
Multiple Airlines Logo
10:33 am - 1:34 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
26h 01m2 stops Tampa Fort Lauderdale
$345Multiple Airlines
Mon, Sep 7 - Sun, Sep 13
American Airlines Logo
1:38 pm - 11:29 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
10h 51m2 stops Miami Philadelphia
American Airlines Logo
4:21 pm - 11:00 amMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
17h 39m2 stops Charlotte Douglas Miami
$346American Airlines
Sun, Sep 6 - Fri, Sep 11
Delta Logo
2:59 pm - 10:38 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
8h 39m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:32 am - 10:19 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
11h 47m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$346Delta
Sun, Sep 6 - Thu, Sep 10
Delta Logo
2:59 pm - 10:38 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
8h 39m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:50 am - 4:49 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
9h 59m1 stop Atlanta Hartsfield-Jackson
$346Delta
Fri, Sep 25 - Sat, Oct 3
United Airlines Logo
12:52 pm - 11:53 amMBJ  Montego Bay Sangster Intl-MSN Madison Truax Field
23h 01m2 stops Newark Chicago O'Hare Intl
United Airlines Logo
2:49 pm - 11:43 amMSN  Madison Truax Field-MBJ Montego Bay Sangster Intl
20h 54m2 stops Chicago O'Hare Intl Newark
$352United Airlines
Fri, Sep 18 - Fri, Sep 25
American Airlines Logo
2:22 pm - 11:30 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
10h 08m1 stop Philadelphia
American Airlines Logo
2:17 pm - 9:24 amMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
18h 07m2 stops Charlotte Douglas Miami
$354American Airlines
Fri, Sep 18 - Fri, Sep 25
American Airlines Logo
6:00 am - 3:51 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
10h 51m2 stops Miami Washington, D.C. Reagan-National
American Airlines Logo
2:17 pm - 9:24 amMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
18h 07m2 stops Charlotte Douglas Miami
$354American Airlines
Wed, Sep 2 - Wed, Sep 9
American Airlines Logo
2:33 pm - 11:29 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
9h 56m1 stop Philadelphia
American Airlines Logo
6:00 am - 8:47 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
13h 47m2 stops Washington, D.C. Reagan-National Miami
$358American Airlines
Wed, Sep 2 - Wed, Sep 9
American Airlines Logo
3:47 pm - 11:59 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
9h 12m2 stops Charlotte Douglas Washington, D.C. Reagan-National
American Airlines Logo
6:57 am - 8:47 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
12h 50m2 stops New York LaGuardia Miami
$358American Airlines
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Good to know

Low season

January

Cheapest flight

$144
Best time to beat the crowds but there is an average 34% increase in price.
Most popular time to fly and prices are also 10% lower on average.
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.

Everything you need to know for your flight to Madison

Information on the airport you'll fly into in Madison

Madison (MSN)