$128 Find Cheap Flights from Caribbean to Madison

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Madison departing on 2/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$281
Typical prices: $481-$574
American Airlines
Thu 2/12Mon 2/16
SJU - MSN • 1 stop
Cheapest one-way
$128
Typical prices: $185-$364
Delta
Fri 2/6
SJU - MSN • 2 stops
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Caribbean to Madison

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean to Madison that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean to Madison

Thu, Feb 12 - Mon, Feb 16
American Airlines Logo
5:18 pm - 11:40 pm
SJU
-
MSN
8h 22m
1 stop
American Airlines Logo
7:00 am - 9:49 pm
MSN
-
SJU
12h 49m
1 stop
$281American Airlines
Wed, Feb 25 - Sat, Feb 28
United Airlines Logo
8:30 am - 2:57 pm
SJU
-
MSN
8h 27m
1 stop
United Airlines Logo
3:53 pm - 6:11 am
MSN
-
SJU
12h 18m
2 stops
$346United Airlines
Sat, Mar 28 - Sat, Apr 4
JetBlue Logo
2:07 pm - 9:06 pm
SJU
-
MSN
7h 59m
1 stop
JetBlue Logo
5:30 am - 1:27 pm
MSN
-
SJU
6h 57m
1 stop
$356JetBlue
Tue, Mar 3 - Sat, Mar 7
American Airlines Logo
5:25 pm - 9:11 am
SJU
-
MSN
17h 46m
1 stop
American Airlines Logo
8:22 pm - 5:24 am
MSN
-
SJU
7h 02m
1 stop
$378American Airlines
Sat, Jan 31 - Wed, Feb 4
Multiple Airlines Logo
6:00 am - 5:36 pm
SJU
-
MSN
13h 36m
1 stop
Multiple Airlines Logo
6:36 pm - 9:47 am
MSN
-
SJU
13h 11m
1 stop
$387Multiple Airlines
Wed, Jan 28 - Wed, Feb 4
United Airlines Logo
8:35 am - 2:52 pm
SJU
-
MSN
8h 17m
1 stop
United Airlines Logo
8:15 am - 9:26 pm
MSN
-
SJU
11h 11m
2 stops
$420United Airlines
Thu, Feb 12 - Mon, Feb 16
American Airlines Logo
2:23 pm - 11:40 pm
SJU
-
MSN
11h 17m
2 stops
American Airlines Logo
7:00 am - 9:49 pm
MSN
-
SJU
12h 49m
1 stop
$444American Airlines
Wed, Mar 4 - Tue, Mar 17
Delta Logo
4:05 pm - 10:48 pm
MBJ
-
MSN
7h 43m
1 stop
Delta Logo
6:00 am - 1:27 pm
MSN
-
MBJ
7h 27m
1 stop
$483Delta
Thu, Jul 9 - Fri, Jul 31
American Airlines Logo
12:39 am - 10:39 am
SJU
-
MSN
11h 00m
1 stop
American Airlines Logo
7:02 am - 10:51 pm
MSN
-
SJU
14h 49m
1 stop
$486American Airlines
Wed, May 27 - Tue, Jun 9
Delta Logo
4:55 pm - 8:46 am
MBJ
-
MSN
15h 51m
2 stops
Delta Logo
5:45 am - 1:05 pm
MSN
-
MBJ
7h 20m
1 stop
$515Delta
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$128
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly with an average 5% increase in price.
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.
7.9
DeltaOverall score based on 8051 reviews
8.1Boarding
7.8Entertainment
7.2Food
7.9Comfort
8.5Crew
Airline reviews

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

10.0 ExcellentEric, Jan 2026
SFO - ATL
Read more Delta reviews

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

Delta flight Delay for ,more that two hours i.e original flight was 6.30 PM and it starts at 8.45 PM, When we connect Delta team for meal vouchers as it is late arrival in designation,But we did not get it as per delta policy , which is not good for mid night arrival,

Inexperienced boarding crew allowed too many bags on to a full flight and delayed takeoff causing a missed connection and unplanned overnight stay. There was a hotel at the airport but Delta would not pay for it offering only to shuttle me to an area hotel. Never even offerred so much as an apology by anyone working for Delta.

Staff was great! Kind and cordial! Middle seat row 28 seat B has a hump in it. Trays were getting stuck when putting down and up. Good flight

Departure was delayed resulting in me missing my connection. Delta did not autimatically find me another flight.

The seats weren’t reclining even though it wasn’t as exit seat

It was good because we traveled without luggage, carry on only.

We departed late, and we arrived to Atlanta late for our connecting flight to Quito. I asked the flight attendant before landing to please make an announcement and let us go out of the plane first she agreed but never did the announcement. We run and arrived 3 minutes late and they closed the gate of the plane. We ended up staying one day in Atlanta for the next flight to Quito. When we arrived to Quito 2 of our 50lbs bags arrived completely broken and destroyed. I made the complaint and so far nobody in Delta wants to help.

I usually get upgraded so my experience is usually amazing. I did not get upgraded this time - which was fine - but the wifi had issues, the monitors were going in & out, & (though not Delta's fault) one of the gentlemen next to me desperately needed a shower.

The entertainment screens were not working and there was no air condition the entire flight. Very uncomfortable.

Delayed, no updates, had a rewards number but was not working

The seats from lax to DFW was so tight that I could not move my legs . No WiFi and had to pay . Not a good selection of entertainment

AA should improve their in air internet & entertainment options. Seems unreasonable to charge $20/hr and should have some form of free connections. The entertainment options are also pretty limited, movies are outdated and the series only show 3-5 episodes.

We were upgraded to First Class and it was a great flight

Amazing I love American. I’ll never fly anyone else if I can help it.

I love American. I’ll never fly anyone else if I can help it.

Flight delay and multiple gate changes including a change near boarding time to another terminal, which in DFW is a pain. Pre-boarding delay and also a further delay on the ground after boarding. About an hour and a half total delay.

On the plus side, crew was attentive, drinks were cold, and in-flight entertainment selection was better than some other airlines. On the negative aide, Plane was delayed almost an hour, either no announcements from the gate crew. Biscoff cookies are gross, appreciate airlines that give a choice. Also, crew had no personality or enthusiasm at all.

Little warm on the plane and delayed for an hour

Tell the crew (when boarding) to yell at the imbeciles blocking us from walking up to scan. I promise everyone crowds around and half of us (most the time I’m group 4) have to push our way through. Your staff is awesome, the public - not so much-

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