$129 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

Tue, Oct 20 - Tue, Oct 27
Multiple Airlines Logo
8:45 am - 9:58 amSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
26h 13m2 stops Fort Lauderdale Tampa
Multiple Airlines Logo
10:30 am - 1:50 amMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
14h 20m1 stop Orlando
$328Multiple Airlines
Fri, Dec 4 - Sun, Dec 6
United Airlines Logo
8:25 am - 2:50 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
8h 25m1 stop Chicago O'Hare Intl
United Airlines Logo
6:30 am - 9:24 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
12h 54m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
$356United Airlines
Tue, Oct 20 - Tue, Oct 27
Delta Logo
2:59 pm - 11:03 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
9h 04m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 10:18 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
14h 18m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$356Delta
Tue, Oct 20 - Tue, Oct 27
Delta Logo
2:59 pm - 11:03 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
9h 04m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:14 am - 10:18 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
10h 04m1 stop Atlanta Hartsfield-Jackson
$356Delta
Thu, Dec 3 - Sun, Dec 6
United Airlines Logo
4:55 pm - 11:13 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
8h 18m1 stop Chicago O'Hare Intl
United Airlines Logo
6:30 am - 9:24 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
12h 54m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
$356United Airlines
Thu, Dec 3 - Mon, Dec 7
Delta Logo
1:58 pm - 9:24 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
9h 26m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
11:45 am - 11:13 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
9h 28m1 stop Atlanta Hartsfield-Jackson
$356Delta
Tue, Oct 20 - Tue, Oct 27
United Airlines Logo
1:25 pm - 8:15 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
7h 50m1 stop Newark
United Airlines Logo
6:25 am - 2:40 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
7h 15m1 stop Chicago O'Hare Intl
$356United Airlines
Sat, Oct 17 - Sat, Oct 24
American Airlines Logo
6:00 am - 10:32 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
17h 32m1 stop Dallas/Fort Worth
American Airlines Logo
7:05 pm - 2:03 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
17h 58m1 stop Chicago O'Hare Intl
$386American Airlines
Fri, Dec 11 - Sat, Jan 9
American Airlines Logo
10:32 am - 8:07 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
11h 35m2 stops Miami Chicago O'Hare Intl
American Airlines Logo
9:04 pm - 2:52 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
15h 48m1 stop Chicago O'Hare Intl
$386American Airlines
Fri, Dec 11 - Sat, Jan 9
American Airlines Logo
1:18 pm - 11:59 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
12h 41m2 stops Miami Charlotte Douglas
American Airlines Logo
9:04 pm - 2:52 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
15h 48m1 stop Chicago O'Hare Intl
$386American Airlines
Useful Info

Good to know

Low season

February

Cheapest flight

$129
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 17% 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 10230 reviews
7.7Boarding
7.3Comfort
8.1Crew
6.7Food
7.1Entertainment
Airline reviews

Plane congestion resulted in a 1 hr wait from landing to arrival at the gate. This was in addition to also experiencing extreme delays on my incoming flight.

2.0 MediocreKristel, Sep 2026
Read more United Airlines reviews

Plane congestion resulted in a 1 hr wait from landing to arrival at the gate. This was in addition to also experiencing extreme delays on my incoming flight.

Delayed too much. 1.5 hrs in the airport and another 1 hr in the runway. Got too late in the night. There was no proper food available.

awesome team work seen since on board till off plane in my destination. thanks you so much.

Job well done, being treated for good and helping a lot . thanks you so much till will meet against.

For the Singapore to CA flight, nearly 16 hours long was miserable. We sat on the tarmac for one hour to burn fuel. The flight attendant girls were mean. They would yell at people who stood up to try to stretch their legs. One time the drinks came thru and the lady judged us and made a comment about how much sugar was in apple juice when we ordered it once. She was rude and inappropriate. The entire flight was frustrating. You'd think a long haul like that the airline would try to make you comfortable. I just don't understand why the ladies were so snappy. I have never experienced rude flight attendants like that. It was the longest flight I've had to sit on before. We were not impressed. Raymond on the other hand was amazing! By far the best person working that flight!

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.

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