$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
Overall average: $528
American Airlines
Thu 2/12Mon 2/16
SJU - MSN • 1 stop
Cheapest one-way
$201
Typical prices: $185-$364
Multiple Airlines
Fri 2/6
SJU - MSN • 1 stop
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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
8:24 pm - 5:24 am
MSN
-
SJU
7h 00m
1 stop
$281American Airlines
Fri, Feb 13 - Mon, Feb 16
American Airlines Logo
2:23 pm - 11:40 pm
SJU
-
MSN
11h 17m
2 stops
American Airlines Logo
8:24 pm - 5:24 am
MSN
-
SJU
7h 00m
1 stop
$344American Airlines
Wed, Feb 25 - Sat, Feb 28
United Airlines Logo
8:30 am - 2:07 pm
SJU
-
MSN
7h 37m
1 stop
United Airlines Logo
3:53 pm - 6:11 am
MSN
-
SJU
12h 18m
2 stops
$346United Airlines
Tue, Feb 17 - Tue, Feb 24
American Airlines Logo
5:42 pm - 9:53 am
SJU
-
MSN
18h 11m
1 stop
American Airlines Logo
8:09 am - 9:34 pm
MSN
-
SJU
11h 25m
2 stops
$358American Airlines
Tue, Feb 17 - Tue, Feb 24
American Airlines Logo
7:00 am - 3:42 pm
SJU
-
MSN
10h 42m
2 stops
American Airlines Logo
8:09 am - 8:39 pm
MSN
-
SJU
10h 30m
2 stops
$411American Airlines
Thu, Jan 29 - Sun, Feb 1
United Airlines Logo
2:05 am - 11:51 am
SJU
-
MSN
11h 46m
2 stops
United Airlines Logo
5:25 pm - 6:11 am
MSN
-
SJU
10h 46m
2 stops
$420United Airlines
Wed, May 27 - Wed, Jun 3
Delta Logo
4:55 pm - 8:46 am
MBJ
-
MSN
15h 51m
2 stops
Delta Logo
5:45 am - 3:29 pm
MSN
-
MBJ
9h 44m
1 stop
$515Delta
Sat, Jan 31 - Sat, Feb 14
Delta Logo
2:52 pm - 8:54 pm
MBJ
-
MSN
7h 02m
1 stop
Delta Logo
6:20 am - 2:40 pm
MSN
-
MBJ
7h 20m
1 stop
$537Delta
Mon, Feb 2 - Fri, Feb 6
British Airways Logo
4:24 pm - 11:41 pm
SXM
-
MSN
9h 17m
1 stop
British Airways Logo
4:47 pm - 1:37 pm
MSN
-
SXM
18h 50m
1 stop
$681British Airways
Tue, Mar 3 - Tue, Mar 10
WestJet Logo
8:25 pm - 8:52 pm
MBJ
-
MSN
25h 27m
2 stops
WestJet Logo
7:00 am - 6:17 pm
MSN
-
MBJ
11h 17m
2 stops
$3,303WestJet
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$201
Best time to beat the crowds but there is an average 30% 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.
7.9
DeltaOverall score based on 8075 reviews
8.5Crew
7.2Food
7.9Comfort
7.8Entertainment
8.1Boarding
Airline reviews

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

10.0 ExcellentJay, Jan 2026
ATL - BDL
Read more Delta reviews

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

My requested wheelchair never appeared. So many entertainment choices yet, I found little of interest and no internet option to search on my own. Both were minor issues.

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

It would have been better if the flight wasn't delayed by 2.5 hours

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.

It was a good trip. Flight Attendants were friendly and responsive.

Qatar airways ,boarding arrangements at Hamid international airport could been better

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

My seat tv didn’t work the whole trip. And the seat space is too small despite being seated at the front.

The seat cushions were very worn so they were extremely 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.

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