$182 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

Thu, Dec 3 - Wed, Dec 9
Multiple Airlines Logo
5:01 am - 5:30 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
14h 29m2 stops Atlanta Hartsfield-Jackson Orlando
Multiple Airlines Logo
10:38 am - 7:57 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
7h 19m1 stop Tampa
$419Multiple Airlines
Wed, Nov 25 - Tue, Dec 1
American Airlines Logo
6:23 am - 4:55 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
12h 32m1 stop Dallas/Fort Worth
American Airlines Logo
12:20 pm - 9:27 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
7h 07m1 stop Charlotte Douglas
$426American Airlines
Thu, Apr 8 - Thu, Apr 15
American Airlines Logo
11:59 pm - 11:03 amSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
12h 04m1 stop Dallas/Fort Worth
American Airlines Logo
11:35 am - 8:51 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
8h 16m1 stop Charlotte Douglas
$426American Airlines
Wed, Nov 25 - Tue, Dec 1
American Airlines Logo
4:42 pm - 11:59 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
9h 17m1 stop Charlotte Douglas
American Airlines Logo
12:20 pm - 9:27 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
7h 07m1 stop Charlotte Douglas
$426American Airlines
Wed, Dec 2 - Wed, Dec 9
United Airlines Logo
2:05 am - 1:51 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
13h 46m2 stops Newark Chicago O'Hare Intl
United Airlines Logo
9:12 am - 12:36 amMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
13h 24m2 stops Chicago O'Hare Intl Newark
$516United Airlines
Sat, Nov 21 - Sat, Nov 28
United Airlines Logo
1:07 pm - 9:05 pmSTT  Saint Thomas Island Cyril E King-MSN Madison Truax Field
9h 58m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl
United Airlines Logo
5:00 am - 2:31 pmMSN  Madison Truax Field-STT Saint Thomas Island Cyril E King
7h 31m1 stop Chicago O'Hare Intl
$528United Airlines
Sat, Nov 21 - Sat, Nov 28
United Airlines Logo
3:00 pm - 11:07 pmSTT  Saint Thomas Island Cyril E King-MSN Madison Truax Field
10h 07m1 stop Chicago O'Hare Intl
United Airlines Logo
5:00 am - 2:31 pmMSN  Madison Truax Field-STT Saint Thomas Island Cyril E King
7h 31m1 stop Chicago O'Hare Intl
$528United Airlines
Wed, Dec 30 - Tue, Jan 5
JetBlue Logo
4:20 pm - 9:47 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
7h 27m1 stop Atlanta Hartsfield-Jackson
JetBlue Logo
11:26 am - 11:58 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
10h 32m1 stop Atlanta Hartsfield-Jackson
$732JetBlue
Wed, Dec 30 - Tue, Jan 5
Multiple Airlines Logo
10:51 pm - 5:30 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
20h 39m1 stop Orlando
Multiple Airlines Logo
12:15 pm - 10:15 amMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
20h 00m2 stops Orlando Philadelphia
$758Multiple Airlines
Sun, Dec 20 - Mon, Dec 28
WestJet Logo
12:45 pm - 2:05 pmMBJ  Montego Bay Sangster Intl-MSN Madison Truax Field
50h 20m2 stops Winnipeg Minneapolis St Paul
WestJet Logo
2:45 pm - 7:35 pmMSN  Madison Truax Field-MBJ Montego Bay Sangster Intl
51h 50m2 stops Minneapolis St Paul Toronto Pearson Intl
$2,116WestJet
Useful Info

Good to know

Low season

January

Cheapest flight

$182
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 13% 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.
7.3
United AirlinesOverall score based on 10451 reviews
7.7Boarding
7.3Comfort
8.1Crew
7.1Entertainment
6.7Food
Airline reviews

I need to note that this flight experience was generally fine but the boarding situation was absolutely a mess and there wasn’t any actual priority boarding. I rated the experience poorly because I’m am genuinely so frustrated with the crew on United taking the baggage space in first class. This flight it didn’t happen, but the last few flights (when I ironically don’t get an opportunity to provide feedback) have been spoiled because upon entering the first class cabin as one of the first few seated passengers, the overhead bins are full and ‘crew’’ tags are on the bags of those taking space. I don’t intend to infer some sort of a class or caste system but it’s absolutely ridiculous that the crew takes the overhead storage above and beyond their most loyal and lucrative customers. They should not even have economy space IMO. And I’ve gotten grief when I’ve noted to the crew the ridiculousness of the notion that the crew (who are the last off the plane) should have priority over flyers who pay. I hope you find a way to convey this message to United because it’s happening with increasing frequency and I intend to find a way to expose the specific crew members who are doing this on a flight by flight basis. (And I have a day job)

10.0 ExcellentKristi, Oct 2026
Read more United Airlines reviews

I need to note that this flight experience was generally fine but the boarding situation was absolutely a mess and there wasn’t any actual priority boarding. I rated the experience poorly because I’m am genuinely so frustrated with the crew on United taking the baggage space in first class. This flight it didn’t happen, but the last few flights (when I ironically don’t get an opportunity to provide feedback) have been spoiled because upon entering the first class cabin as one of the first few seated passengers, the overhead bins are full and ‘crew’’ tags are on the bags of those taking space. I don’t intend to infer some sort of a class or caste system but it’s absolutely ridiculous that the crew takes the overhead storage above and beyond their most loyal and lucrative customers. They should not even have economy space IMO. And I’ve gotten grief when I’ve noted to the crew the ridiculousness of the notion that the crew (who are the last off the plane) should have priority over flyers who pay. I hope you find a way to convey this message to United because it’s happening with increasing frequency and I intend to find a way to expose the specific crew members who are doing this on a flight by flight basis. (And I have a day job)

I had bad experience with United airline. No live rep, they only have AI that respond to customers concern

Great flight and crew. Need more legroom and DO NOT allow seats to recline.

Flight and crew were great. Need more legroom and do not allow seats to recline.

The guy in front of me was talking constantly, even when the pilot was making announcements. I found this very disrespectful to the pilot and to others.

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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