$141 Find Cheap Flights from Caribbean Islands 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 9/1. 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 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, Aug 25 - Thu, Sep 3
American Airlines Logo
10:33 am - 11:09 pm
SJU
-
MSN
13h 36m
2 stops
American Airlines Logo
11:33 am - 11:59 pm
MSN
-
SJU
11h 26m
1 stop
$346American Airlines
Sun, Aug 23 - Wed, Sep 2
Multiple Airlines Logo
3:28 pm - 8:25 am
SJU
-
MSN
17h 57m
1 stop
Multiple Airlines Logo
10:27 am - 12:56 am
MSN
-
SJU
13h 29m
1 stop
$349Multiple Airlines
Tue, Oct 20 - Tue, Oct 27
Multiple Airlines Logo
5:12 pm - 9:53 am
SJU
-
MSN
17h 41m
2 stops
Multiple Airlines Logo
10:30 am - 1:50 am
MSN
-
SJU
14h 20m
1 stop
$351Multiple Airlines
Sun, Aug 23 - Wed, Sep 2
Multiple Airlines Logo
3:28 pm - 8:25 am
SJU
-
MSN
17h 57m
1 stop
Multiple Airlines Logo
10:27 am - 12:56 am
MSN
-
SJU
13h 29m
1 stop
$352Multiple Airlines
Tue, Oct 20 - Tue, Oct 27
American Airlines Logo
12:59 pm - 11:17 pm
SJU
-
MSN
11h 18m
1 stop
American Airlines Logo
6:16 am - 2:03 pm
MSN
-
SJU
6h 47m
1 stop
$353American Airlines
Tue, Oct 20 - Tue, Oct 27
American Airlines Logo
12:59 pm - 12:12 am
SJU
-
MSN
12h 13m
2 stops
American Airlines Logo
7:00 am - 10:22 pm
MSN
-
SJU
14h 22m
2 stops
$353American Airlines
Tue, Aug 25 - Fri, Sep 4
American Airlines Logo
6:00 am - 3:24 pm
SJU
-
MSN
10h 24m
2 stops
American Airlines Logo
6:00 am - 6:33 pm
MSN
-
SJU
11h 33m
2 stops
$386American Airlines
Thu, Oct 8 - Mon, Oct 12
American Airlines Logo
3:51 pm - 11:57 pm
SJU
-
MSN
9h 06m
1 stop
American Airlines Logo
7:15 am - 3:01 pm
MSN
-
SJU
6h 46m
1 stop
$386American Airlines
Mon, Aug 24 - Thu, Sep 3
American Airlines Logo
12:55 am - 9:17 am
SJU
-
MSN
9h 22m
1 stop
American Airlines Logo
11:33 am - 11:59 pm
MSN
-
SJU
11h 26m
1 stop
$386American Airlines
Tue, Aug 25 - Thu, Sep 3
American Airlines Logo
10:33 am - 8:27 pm
SJU
-
MSN
10h 54m
2 stops
American Airlines Logo
9:48 am - 11:59 pm
MSN
-
SJU
13h 11m
2 stops
$386American Airlines
Useful Info

Good to know

Low season

January

Cheapest flight

$141
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 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.
7.1
American AirlinesOverall score based on 11845 reviews
7.2Comfort
6.4Food
6.8Entertainment
7.9Crew
7.5Boarding
Airline reviews

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

6.0 GoodSanta, Jul 2026
ORD - MKE
Read more American Airlines reviews

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

there are no options s for snack besides cookies would ve nice to have a salty option n

Never ontime and always delays. Long waits for customer service and often app doesn’t work

We were upgraded to First Class and it was a great flight

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

We loved the steward on the plane. He made the night enjoyable

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

American cancelled our flight home. Zero option for hotel, alternative transportation and took 3 hours to find our bags so we could take a 3 hour UBER ride home on our dime. Never flying AA again.

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Everything you need to know for your flight to Madison

Information on the airport you'll fly into in Madison

Madison (MSN)