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.

Which airlines provide the cheapest flights from Madison to Caribbean?

In the past 5 days, the cheapest round-trip tickets from Madison to Caribbean were found on United Airlines ($296) and Delta ($296).

Which airlines provide the cheapest flights from Madison to Caribbean?

In the past 5 days, the cheapest round-trip tickets from Madison to Caribbean were found on United Airlines ($296) and Delta ($296).

How long does a flight from Madison to Caribbean take?

The duration of a flight to Caribbean depends on your arrival airport. The shortest routes to Caribbean from Madison are to Nassau , which takes 5h 08m , Montego Bay , which takes 6h 23m, and Santo Domingo , which takes 6h 37m.

How long does a flight from Madison to Caribbean take?

The duration of a flight to Caribbean depends on your arrival airport. The shortest routes to Caribbean from Madison are to Nassau , which takes 5h 08m , Montego Bay , which takes 6h 23m, and Santo Domingo , which takes 6h 37m.

$168 CHEAP FLIGHTS from Madison to Caribbean

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Flight Deals

One-wayRound-trip

Punta Cana1 stop$521

Santo Domingo2 stops$605

Montego Bay2 stops$397

Oranjestad1 stop$586

Nassau1 stop$434

Saint Thomas Island2 stops$450

Simpson Bay2 stops$499

Providenciales2 stops$406

Port of Spain1 stop$770

Bridgetown2 stops$972

George Town2 stops$402

Aguadilla2 stops$426

St. John's2 stops$3,715

Punta Cana1 stop$521

Santo Domingo2 stops$605

Montego Bay2 stops$397

Oranjestad1 stop$586

Nassau1 stop$434

Saint Thomas Island2 stops$450

Simpson Bay2 stops$499

Providenciales2 stops$406

Port of Spain1 stop$770

Bridgetown2 stops$972

George Town2 stops$402

Aguadilla2 stops$426

St. John's2 stops$3,715

Book Cheap Madison to Caribbean Plane Tickets

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Recent round-trip flight deals from Madison to Caribbean

Sun, Sep 6 - Tue, Sep 15

6:30 am - 8:38 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 08m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

1:00 am - 12:03 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

12h 03m2 stops Newark Chicago O'Hare Intl

$296United Airlines

Sun, Sep 6 - Tue, Sep 15

6:30 am - 2:44 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

7h 14m1 stop Chicago O'Hare Intl

1:00 am - 12:03 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

12h 03m2 stops Newark Chicago O'Hare Intl

$296United Airlines

Sun, Sep 6 - Wed, Sep 16

1:45 pm - 10:29 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

7h 44m1 stop Atlanta Hartsfield-Jackson

2:59 pm - 10:41 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

8h 42m1 stop Atlanta Hartsfield-Jackson

$296Delta

Tue, Jan 19 - Fri, Jan 22

11:00 am - 11:50 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

10h 50m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

5:15 pm - 10:55 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

7h 40m1 stop Minneapolis St Paul

$296Delta

Tue, Sep 15 - Mon, Sep 21

5:00 am - 2:44 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

8h 44m1 stop Chicago O'Hare Intl

1:00 am - 10:14 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

10h 14m1 stop Newark

$296United Airlines

Tue, Jan 19 - Fri, Jan 22

11:00 am - 11:50 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

10h 50m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

6:15 am - 8:45 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

16h 30m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County

$296Delta

Wed, Sep 2 - Tue, Sep 8

10:27 am - 12:56 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 29m1 stop Tampa

6:35 am - 9:53 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

28h 18m2 stops Fort Lauderdale Tampa

$311Multiple Airlines

Wed, Sep 2 - Tue, Sep 8

10:27 am - 12:56 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 29m1 stop Tampa

5:37 pm - 9:53 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

17h 16m1 stop Tampa

$321Multiple Airlines

Fri, Sep 11 - Mon, Sep 14

8:05 pm - 2:50 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

17h 45m2 stops Chicago O'Hare Intl Charlotte Douglas

11:51 am - 11:30 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

12h 39m2 stops Miami Philadelphia

$346American Airlines

Thu, Nov 12 - Tue, Nov 17

6:38 pm - 9:42 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 04m2 stops Charlotte Douglas Miami

8:00 am - 4:53 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

10h 53m2 stops Miami Philadelphia

$346American Airlines

Recent last minute flight deals from Madison to Caribbean

Sat, Aug 15 - Fri, Aug 21

10:27 am - 12:41 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 14m1 stop Tampa

6:35 am - 9:47 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

28h 12m2 stops Fort Lauderdale Tampa

$396Multiple Airlines

Sat, Aug 15 - Tue, Aug 18

10:27 am - 12:41 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 14m1 stop Tampa

3:10 am - 5:25 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

15h 15m1 stop Orlando

$425Multiple Airlines

Sat, Aug 15 - Tue, Aug 25

10:27 am - 12:41 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 14m1 stop Tampa

6:35 am - 9:47 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

28h 12m2 stops Fort Lauderdale Tampa

$427Multiple Airlines

Sat, Aug 15 - Sat, Aug 22

9:32 am - 10:29 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

11h 57m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson

12:56 pm - 10:38 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

10h 42m1 stop Atlanta Hartsfield-Jackson

$580Delta

Wed, Aug 12 - Fri, Aug 14

9:48 am - 11:15 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

12h 27m1 stop Chicago O'Hare Intl

3:47 pm - 11:09 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

8h 22m1 stop Charlotte Douglas

$585American Airlines

Wed, Aug 12 - Fri, Aug 14

7:47 am - 9:55 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 08m2 stops Chicago O'Hare Intl Miami

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

$585American Airlines

Sat, Aug 15 - Tue, Aug 25

6:30 am - 8:38 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 08m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

3:56 pm - 10:41 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

7h 45m1 stop Chicago O'Hare Intl

$658United Airlines

Sat, Aug 15 - Tue, Aug 25

6:30 am - 8:38 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 08m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

1:00 am - 11:58 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

11h 58m2 stops Newark Chicago O'Hare Intl

$658United Airlines

Sat, Aug 15 - Wed, Aug 19

8:10 am - 8:38 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

11h 28m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

7:00 am - 8:56 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

14h 56m2 stops Houston George Bush Intcntl Chicago O'Hare Intl

$670United Airlines

Sat, Aug 15 - Fri, Aug 21

1:26 pm - 11:43 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

9h 17m2 stops Washington, D.C. Reagan-National Charlotte Douglas

10:33 am - 8:27 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

10h 54m2 stops Miami Dallas/Fort Worth

$688American 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.

Prices

Airlines

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

The cheapest month for flights from Madison to Caribbean is August, when tickets cost $449 (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 $738 respectively.

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

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 18% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Find deals

Low season	July
High season	January
Cheapest flight	$168

Best time to beat the crowds but there is an average 4% increase in price.

Most popular time to fly and prices are also 9% lower on average.

Flight from Madison to San Juan

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

Airports

Cabin class

Complete your trip

Flights to other cities

Origins

Popular routes

Return flight deals

Information on your arrival and departure airports

Madison (MSN)

$168 Find Cheap Flights from Madison to Caribbean - Compare and Save

Cheap Flights from Madison to Caribbean

Book Cheap Madison to Caribbean Plane Tickets

Recent round-trip flight deals from Madison to Caribbean

Recent one-way flight deals from Madison to Caribbean

Recent last minute flight deals from Madison to Caribbean

KAYAK's insights & trends for Madison to Caribbean flights

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

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

Which airlines provide the cheapest flights from Madison to Caribbean?

How long does a flight from Madison to Caribbean take?

Good to know

Low season

High season

Cheapest flight

FAQs - booking Caribbean flights

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Cabin class types available on flights to Madison

Complete your trip to Caribbean with a hotel stay or car rental

Flights to other popular destinations

Flights from domestic origins to Madison

Flights to popular destinations in Caribbean

Find deals for your return flight