$133 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 10/27. 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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Flight Deals

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

Thu, Sep 24 - Mon, Sep 28
Delta Logo
2:59 pm - 10:53 pm
SJU
-
MSN
8h 54m
1 stop
Delta Logo
6:00 am - 4:49 pm
MSN
-
SJU
9h 49m
1 stop
$266Delta
Wed, Sep 2 - Sat, Sep 5
Delta Logo
7:30 am - 9:19 pm
SJU
-
MSN
14h 49m
2 stops
Delta Logo
1:45 pm - 10:29 pm
MSN
-
SJU
7h 44m
1 stop
$296Delta
Thu, Sep 24 - Mon, Sep 28
American Airlines Logo
4:19 pm - 10:51 am
SJU
-
MSN
19h 32m
1 stop
American Airlines Logo
6:00 am - 8:47 pm
MSN
-
SJU
13h 47m
2 stops
$326American Airlines
Tue, Aug 4 - Tue, Aug 11
United Airlines Logo
1:00 am - 10:09 am
SJU
-
MSN
10h 09m
1 stop
United Airlines Logo
5:00 am - 8:38 pm
MSN
-
SJU
14h 38m
2 stops
$327United Airlines
Thu, Sep 17 - Thu, Sep 24
United Airlines Logo
12:52 pm - 8:53 pm
MBJ
-
MSN
32h 01m
2 stops
United Airlines Logo
2:49 pm - 1:30 pm
MSN
-
MBJ
46h 41m
2 stops
$333United Airlines
Fri, Aug 21 - Wed, Aug 26
JetBlue Logo
7:00 am - 4:20 pm
SJU
-
MSN
10h 20m
1 stop
JetBlue Logo
5:43 am - 4:38 pm
MSN
-
SJU
9h 55m
1 stop
$336JetBlue
Thu, Aug 20 - Wed, Aug 26
American Airlines Logo
12:55 am - 9:22 am
SJU
-
MSN
9h 27m
1 stop
American Airlines Logo
6:30 am - 6:33 pm
MSN
-
SJU
11h 03m
2 stops
$337American Airlines
Thu, Sep 24 - Thu, Oct 1
American Airlines Logo
5:16 pm - 12:26 pm
MBJ
-
MSN
19h 10m
2 stops
American Airlines Logo
5:50 pm - 12:53 pm
MSN
-
MBJ
19h 03m
2 stops
$341American Airlines
Thu, Sep 17 - Thu, Sep 24
American Airlines Logo
5:16 pm - 10:51 am
MBJ
-
MSN
17h 35m
2 stops
American Airlines Logo
5:51 pm - 4:16 pm
MSN
-
MBJ
22h 25m
1 stop
$348American Airlines
Sun, Jul 26 - Sun, Aug 2
JetBlue Logo
6:00 am - 3:51 pm
SJU
-
MSN
10h 51m
1 stop
JetBlue Logo
5:48 am - 1:32 pm
MSN
-
SJU
6h 44m
1 stop
$366JetBlue
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Good to know

Low seasonJanuary
Cheapest flight$133
Best time to beat the crowds but there is an average 35% increase in price.
Most popular time to fly and prices are also 9% 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)