$160 Find Cheap Flights from Caribbean to Madison - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Useful Info
Flight Deals

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 30 - Tue, Nov 3
Multiple Airlines Logo
6:15 am - 9:58 amSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
28h 43m2 stops Fort Lauderdale Tampa
Multiple Airlines Logo
10:30 am - 10:15 amMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
21h 45m1 stop Orlando
$325Multiple Airlines
Fri, Oct 30 - Tue, Nov 3
Multiple Airlines Logo
4:36 pm - 9:58 amSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
18h 22m1 stop Tampa
Multiple Airlines Logo
10:30 am - 10:15 amMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
21h 45m1 stop Orlando
$351Multiple Airlines
Tue, Nov 10 - Tue, Nov 17
Multiple Airlines Logo
8:45 am - 9:58 amSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
27h 13m2 stops Fort Lauderdale Tampa
Multiple Airlines Logo
10:30 am - 2:46 amMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
14h 16m1 stop Orlando
$374Multiple Airlines
Tue, Nov 10 - Tue, Nov 17
United Airlines Logo
4:55 pm - 11:07 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
8h 12m1 stop Chicago O'Hare Intl
United Airlines Logo
5:00 am - 3:40 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
8h 40m1 stop Chicago O'Hare Intl
$376United Airlines
Tue, Nov 10 - Tue, Nov 17
United Airlines Logo
7:40 am - 5:02 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
11h 22m2 stops Houston George Bush Intcntl Chicago O'Hare Intl
United Airlines Logo
8:15 am - 9:24 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
11h 09m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
$376United Airlines
Fri, Dec 11 - Sat, Jan 9
American Airlines Logo
2:28 pm - 11:19 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
10h 51m2 stops Charlotte Douglas Chicago O'Hare Intl
American Airlines Logo
6:00 am - 9:11 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
13h 11m2 stops Washington, D.C. Reagan-National Charlotte Douglas
$406American Airlines
Fri, Dec 11 - Sat, Jan 9
American Airlines Logo
7:00 am - 11:56 amSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
6h 56m1 stop Charlotte Douglas
American Airlines Logo
6:00 am - 9:11 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
13h 11m2 stops Washington, D.C. Reagan-National Charlotte Douglas
$406American Airlines
Mon, Nov 2 - Mon, Nov 16
American Airlines Logo
3:22 pm - 11:00 pmMBJ  Montego Bay Sangster Intl-MSN Madison Truax Field
8h 38m1 stop Charlotte Douglas
American Airlines Logo
6:02 am - 2:52 pmMSN  Madison Truax Field-MBJ Montego Bay Sangster Intl
7h 50m1 stop Chicago O'Hare Intl
$416American Airlines
Mon, Nov 2 - Mon, Nov 16
United Airlines Logo
2:54 pm - 9:05 pmMBJ  Montego Bay Sangster Intl-MSN Madison Truax Field
7h 11m1 stop Chicago O'Hare Intl
United Airlines Logo
7:00 pm - 12:13 pmMSN  Madison Truax Field-MBJ Montego Bay Sangster Intl
16h 13m2 stops Chicago O'Hare Intl Newark
$416United Airlines
Tue, Nov 3 - Thu, Nov 5
Multiple Airlines Logo
8:45 am - 9:58 amSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
27h 13m2 stops Fort Lauderdale Tampa
Multiple Airlines Logo
6:00 pm - 10:15 amMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
14h 15m1 stop Orlando
$457Multiple Airlines
Useful Info

Good to know

Low season

January

Cheapest flight

$160
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 11% 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 airlines 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.
7.4
United AirlinesOverall score based on 10366 reviews
8.1Crew
6.7Food
7.7Boarding
7.1Entertainment
7.3Comfort
Airline reviews

Requested for warm or hot water because of throat pain, it was denied. The entertainment system was hung, requested the crew to turn it off, instead of turning it off they rebooted the device. It was stuck again, no one bothered to check.

2.0 MediocreKranthi Kumar, Oct 2026
Read more United Airlines reviews

Requested for warm or hot water because of throat pain, it was denied. The entertainment system was hung, requested the crew to turn it off, instead of turning it off they rebooted the device. It was stuck again, no one bothered to check.

Horrible on the chicago end. They change hates then there is a plane at the new gate so we can’t pull in. Then that plane has mechanical issue and needs to be pulled back to the gate but we can’t get to another new gate due the other plane being in the way. Horrible gate management which will cause many customers to miss connections.

- delayed because video screens not working - delayed getting a gate at DCA Just continued bad experience IAH to DCA.

Bag got checked but I thought one personal item was guaranteed.

I couldn’t give an honest evaluation, because the Houston airport has a problem and I was stand up for several hours and after a long trip from Munich I feel really very tired

Really delayed, no effort to support customers other than “sometimes we run late.”

Deplaning was delayed because of Jetbridge equipment issues in MKE, causing an issue on an otherwise great flight.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

No real agent onsite helping you for missing luggage there. Not like the other airline next to UA desk, they have staff attending in their desk assisting answer/helping luggage issue, even after midnight.

The wi-fi was awful. I paid $8 each way and got little , except frustration. .

Our gate was changed several times, and the gate agents were just as in the dark as all of us in knowing when our plane would arrive at PHL.

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.

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.

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Baraboo
Windsor
Evansville
Waterloo
Oxford
Cambridge

More options for your flight to Madison