$123 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

Fri, Oct 16 - Sun, Oct 18
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
$316United 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
$328United Airlines
Sat, Sep 26 - Tue, Sep 29
Multiple Airlines Logo
6:42 pm - 5:20 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
23h 38m1 stop Orlando
Multiple Airlines Logo
12:15 pm - 1:52 amMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
12h 37m1 stop Orlando
$334Multiple Airlines
Sat, Sep 26 - Wed, Oct 7
Multiple Airlines Logo
9:50 pm - 5:20 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
20h 30m1 stop Orlando
Multiple Airlines Logo
10:33 am - 1:31 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
25h 58m2 stops Tampa Fort Lauderdale
$345Multiple Airlines
Sat, Sep 26 - Wed, Oct 7
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
$359United 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
$361United Airlines
Thu, Oct 15 - Mon, Oct 19
American Airlines Logo
3:51 pm - 11:57 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
9h 06m1 stop Charlotte Douglas
American Airlines Logo
6:00 am - 10:57 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
15h 57m1 stop Philadelphia
$366American Airlines
Fri, Sep 25 - Sun, Sep 27
American Airlines Logo
3:35 pm - 10:57 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
8h 22m1 stop Dallas/Fort Worth
American Airlines Logo
4:20 pm - 11:00 amMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
17h 40m2 stops Washington, D.C. Reagan-National Miami
$366American Airlines
Sat, Sep 26 - Tue, Sep 29
American Airlines Logo
2:22 pm - 9:43 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
8h 21m1 stop Philadelphia
American Airlines Logo
8:05 pm - 1:57 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
16h 52m2 stops Chicago O'Hare Intl Miami
$372American Airlines
Fri, Sep 25 - Sun, Sep 27
Multiple Airlines Logo
4:39 pm - 9:53 amSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
18h 14m1 stop Tampa
Multiple Airlines Logo
6:00 pm - 5:43 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
22h 43m1 stop Orlando
$418Multiple Airlines
Useful Info

Good to know

Low season

January

Cheapest flight

$123
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 11969 reviews
7.2Comfort
6.8Entertainment
7.5Boarding
7.9Crew
6.4Food
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)