$148 Find Cheap Flights from Madison to Caribbean - 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 from Madison to Caribbean departing on 9/6. 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 Madison to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$526
Santo Domingo
Santo Domingo1 stop$600
Montego Bay
Montego Bay1 stop$392
Oranjestad
Oranjestad2 stops$490
Nassau
Nassau1 stop$470
Saint Thomas Island
Saint Thomas Island2 stops$450
Simpson Bay
Simpson Bay2 stops$470
Providenciales
Providenciales1 stop$423
Port of Spain
Port of Spain2 stops$774
Bridgetown
Bridgetown2 stops$752
George Town
George Town1 stop$419
Aguadilla
Aguadilla2 stops$426
St. John's
St. John's2 stops$815
Punta Cana
Punta Cana1 stop$526
Santo Domingo
Santo Domingo1 stop$600
Montego Bay
Montego Bay1 stop$392
Oranjestad
Oranjestad2 stops$490
Nassau
Nassau1 stop$470
Saint Thomas Island
Saint Thomas Island2 stops$450
Simpson Bay
Simpson Bay2 stops$470
Providenciales
Providenciales1 stop$423
Port of Spain
Port of Spain2 stops$774
Bridgetown
Bridgetown2 stops$752
George Town
George Town1 stop$419
Aguadilla
Aguadilla2 stops$426
St. John's
St. John's2 stops$815

Book Cheap Madison to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Madison to Caribbean 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 Madison to Caribbean

Mon, Sep 14 - Tue, Sep 22
Delta Logo
6:00 am - 10:19 pm
MSN
-
SJU
15h 19m
2 stops
Delta Logo
2:59 pm - 10:41 pm
SJU
-
MSN
8h 42m
1 stop
$296Delta
Tue, Sep 15 - Mon, Sep 21
United Airlines Logo
6:30 am - 8:38 pm
MSN
-
SJU
13h 08m
2 stops
United Airlines Logo
1:00 am - 10:14 am
SJU
-
MSN
10h 14m
1 stop
$296United Airlines
Tue, Sep 15 - Mon, Sep 21
United Airlines Logo
6:30 am - 2:44 pm
MSN
-
SJU
7h 14m
1 stop
United Airlines Logo
1:00 am - 10:14 am
SJU
-
MSN
10h 14m
1 stop
$296United Airlines
Wed, Sep 16 - Tue, Sep 22
Multiple Airlines Logo
10:33 am - 1:34 pm
MSN
-
SJU
26h 01m
2 stops
Multiple Airlines Logo
6:05 pm - 9:53 am
SJU
-
MSN
16h 48m
1 stop
$307Multiple Airlines
Sat, Sep 12 - Tue, Sep 22
Multiple Airlines Logo
10:33 am - 1:34 pm
MSN
-
SJU
26h 01m
2 stops
Multiple Airlines Logo
6:05 pm - 9:53 am
SJU
-
MSN
16h 48m
1 stop
$311Multiple Airlines
Fri, Sep 11 - Tue, Sep 22
Delta Logo
11:33 am - 10:19 pm
MSN
-
SJU
9h 46m
1 stop
Delta Logo
2:59 pm - 10:41 pm
SJU
-
MSN
8h 42m
1 stop
$321Delta
Fri, Sep 11 - Tue, Sep 22
Delta Logo
9:32 am - 10:19 pm
MSN
-
SJU
11h 47m
2 stops
Delta Logo
2:59 pm - 10:41 pm
SJU
-
MSN
8h 42m
1 stop
$321Delta
Sat, Oct 31 - Fri, Nov 6
United Airlines Logo
10:46 am - 11:36 pm
MSN
-
SJU
11h 50m
2 stops
United Airlines Logo
4:55 pm - 10:59 pm
SJU
-
MSN
8h 04m
1 stop
$321United Airlines
Sun, Sep 6 - Wed, Sep 16
American Airlines Logo
9:48 am - 11:15 pm
MSN
-
SJU
12h 27m
1 stop
American Airlines Logo
6:00 am - 3:51 pm
SJU
-
MSN
10h 51m
2 stops
$346American Airlines
Mon, Oct 19 - Wed, Oct 28
American Airlines Logo
6:00 am - 10:57 pm
MSN
-
SJU
15h 57m
1 stop
American Airlines Logo
10:36 am - 9:16 pm
SJU
-
MSN
11h 40m
2 stops
$346American Airlines
Booking Insights

KAYAK's insights & trends for Madison to Caribbean flights

Get data-powered insights and trends into flights from Madison to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Madison to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Madison to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Madison to Caribbean is August, when tickets cost $422 (return) on average. On the other hand, the most expensive months are June and March, when the average cost of round-trip tickets is $745 and $724 respectively.

How far in advance should I book a flight from Madison to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Madison to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Madison to Caribbean, you should book around 2 weeks before departure, which saves you about 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Find deals

Good to know

Low season

July

Cheapest flight

$148
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Madison to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Madison to Caribbean?

    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 Madison to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Madison to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Madison to 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 Madison to Caribbean?

    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 from Madison to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Madison to Caribbean?

    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 from Madison to 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 Caribbean

Information on your arrival and departure airports

Madison (MSN)