$158 Find Cheap Flights from Caribbean to Madison - Compare and Save

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Cheap Flights from Caribbean to Madison

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

Recent round-trip flight deals from Caribbean to Madison

Wed, Oct 14 - Mon, Oct 19
United Airlines Logo
1:00 am - 1:37 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
13h 37m2 stops Newark Chicago O'Hare Intl
United Airlines Logo
6:49 am - 2:44 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
6h 55m1 stop Chicago O'Hare Intl
$406United Airlines
Wed, Oct 14 - Mon, Oct 19
United Airlines Logo
1:00 am - 1:37 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
13h 37m2 stops Newark Chicago O'Hare Intl
United Airlines Logo
6:49 am - 2:44 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
6h 55m1 stop Chicago O'Hare Intl
$431United Airlines
Thu, Oct 15 - Mon, Oct 19
United Airlines Logo
3:56 pm - 10:35 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
7h 39m1 stop Chicago O'Hare Intl
United Airlines Logo
6:49 am - 2:44 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
6h 55m1 stop Chicago O'Hare Intl
$431United Airlines
Thu, Oct 15 - Mon, Oct 19
United Airlines Logo
3:56 pm - 10:35 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
7h 39m1 stop Chicago O'Hare Intl
United Airlines Logo
6:49 am - 2:44 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
6h 55m1 stop Chicago O'Hare Intl
$462United Airlines
Wed, Oct 7 - Wed, Oct 14
United Airlines Logo
2:35 pm - 1:37 pmNAS  Nassau Intl-MSN Madison Truax Field
24h 02m2 stops Newark Chicago O'Hare Intl
United Airlines Logo
5:00 am - 1:47 pmMSN  Madison Truax Field-NAS Nassau Intl
31h 47m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
$541United Airlines
Wed, Oct 7 - Wed, Oct 14
American Airlines Logo
12:20 pm - 9:31 pmNAS  Nassau Intl-MSN Madison Truax Field
10h 11m1 stop Charlotte Douglas
American Airlines Logo
7:00 am - 5:56 pmMSN  Madison Truax Field-NAS Nassau Intl
9h 56m2 stops New York LaGuardia Miami
$559American Airlines
Wed, Oct 7 - Wed, Oct 14
American Airlines Logo
12:20 pm - 9:31 pmNAS  Nassau Intl-MSN Madison Truax Field
10h 11m1 stop Charlotte Douglas
American Airlines Logo
7:14 am - 1:23 pmMSN  Madison Truax Field-NAS Nassau Intl
5h 09m1 stop Charlotte Douglas
$593American Airlines
Sat, Dec 19 - Sat, Dec 26
American Airlines Logo
7:00 am - 3:56 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
10h 56m2 stops Miami Charlotte Douglas
American Airlines Logo
8:32 pm - 2:48 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
16h 16m1 stop Chicago O'Hare Intl
$939American Airlines
Fri, Dec 18 - Sat, Dec 26
American Airlines Logo
1:20 am - 10:45 amSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
11h 25m1 stop Dallas/Fort Worth
American Airlines Logo
8:32 pm - 2:48 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
16h 16m1 stop Chicago O'Hare Intl
$1,005American Airlines
Useful Info

Good to know

Low season

January

Cheapest flight

$158
Best time to beat the crowds but there is an average 33% increase in price.
Most popular time to fly and prices are also 12% 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.

Reviews of the top airline flying from Caribbean to Madison

 
Need help choosing which airline to fly with from Caribbean 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 11998 reviews
6.4Food
7.2Comfort
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
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)