$123 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 5/7. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Madison

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

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

Fri, May 8 - Tue, Sep 8
American Airlines Logo
2:29 pm - 11:54 pm
MBJ
-
MSN
9h 25m
1 stop
American Airlines Logo
6:00 am - 1:58 pm
MSN
-
MBJ
7h 58m
1 stop
$316American Airlines
Sat, May 2 - Sat, May 9
American Airlines Logo
1:15 pm - 11:38 pm
MBJ
-
MSN
10h 23m
1 stop
American Airlines Logo
6:45 am - 1:25 pm
MSN
-
MBJ
6h 40m
1 stop
$318American Airlines
Fri, May 8 - Sun, Aug 30
American Airlines Logo
12:56 pm - 11:54 pm
MBJ
-
MSN
10h 58m
2 stops
American Airlines Logo
8:26 pm - 1:28 pm
MSN
-
MBJ
17h 02m
2 stops
$321American Airlines
Sat, May 2 - Sat, May 9
American Airlines Logo
12:56 pm - 11:56 pm
MBJ
-
MSN
11h 00m
2 stops
American Airlines Logo
8:24 pm - 11:24 am
MSN
-
MBJ
15h 00m
2 stops
$323American Airlines
Thu, May 7 - Tue, May 12
American Airlines Logo
1:25 pm - 11:28 pm
SJU
-
MSN
11h 03m
1 stop
American Airlines Logo
6:45 am - 8:51 pm
MSN
-
SJU
13h 06m
1 stop
$326American Airlines
Mon, May 4 - Wed, Sep 2
American Airlines Logo
4:37 pm - 10:53 am
MBJ
-
MSN
18h 16m
2 stops
American Airlines Logo
6:38 am - 1:28 pm
MSN
-
MBJ
6h 50m
1 stop
$327American Airlines
Thu, May 7 - Mon, May 11
Multiple Airlines Logo
7:00 am - 8:25 am
SJU
-
MSN
26h 25m
1 stop
Multiple Airlines Logo
6:50 pm - 2:08 am
MSN
-
SJU
30h 18m
2 stops
$330Multiple Airlines
Thu, May 7 - Mon, May 11
American Airlines Logo
6:00 am - 11:28 pm
SJU
-
MSN
18h 28m
1 stop
American Airlines Logo
8:24 pm - 2:18 pm
MSN
-
SJU
16h 54m
1 stop
$336American Airlines
Tue, May 12 - Tue, May 19
United Airlines Logo
7:20 am - 7:07 pm
SJU
-
MSN
12h 47m
2 stops
United Airlines Logo
6:30 am - 2:44 pm
MSN
-
SJU
7h 14m
1 stop
$384United Airlines
Thu, May 7 - Thu, May 14
United Airlines Logo
2:40 pm - 10:54 pm
MBJ
-
MSN
32h 14m
2 stops
United Airlines Logo
2:30 pm - 1:30 pm
MSN
-
MBJ
23h 00m
2 stops
$432United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$127
Best time to beat the crowds but there is an average 39% increase in price.
Most popular time to fly and prices are also 8% 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 8406 reviews
8.1Boarding
7.9Comfort
7.2Food
8.5Crew
7.8Entertainment
Airline reviews

The tray table was broken and the food was terrible.

4.0 OkayJeremy, Apr 2026
BNA - BOS
Read more Delta reviews

The tray table was broken and the food was terrible.

The gentleman at the gate I think his name is RIE was exceptional

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

No entertainment. Plane was so small had to pink tag a carry on ive used for 20 years easily on board. The fact the flight got in at midnight, had to wait for crew in fort wayne to allow the plane to approach the gate, THEN had to wait for bag on jet bridge made experience irritating at best.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

Would have been better if there was a nonstop flight from Tampa to Norfolk or Tampa to New Port News.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

The flight was smooth, the crew was great but the plane was quite old

Everything was great until I lost my water bottle and they can’t seem to locate it. I know I left it on the plane though.

I almost missed my flight and they helped me out enormously

Business class was very good, one of my best flights

The "on the ground" A/C was not working. It was so hot while waiting to get in the air, a passenger from the rear of the plan declared "I just can't!" and waited in the gangway until time to close the doors. It was miserable. But the crew were champs and had an amazing attitude. I know they were as miserable as we were but didn't let that affect their performance.

The captain announced to the cabin there would be a delay because they observed a "cut" on a tire during precheck that needed to be cleared by maintenance. We were delayed during this inspection and allowed to proceed after maintenance "measured the cut and decided it was acceptable". My complaint is not about the delay or due diligence. I wish the captain had been more generic when making his announcement. I was a nervous wreck all the way to Charlotte worried that we would have a blowout when landing!

The SFO Lounge crew were amazing. The bartender Faris was great. Thanks!

The flight was on time and the landing was very smooth. The crew and flight attendants were all very friendly and professional.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

American Airlines is a miserable experience. It is predictably miserable, in the sense that every time I fly American, I brace myself for the certainty that it will be unpleasant and uncomfortable. But it is unpredictable in the sense that I never know if the flight will be on time or delayed nine hours (both happened to me this week). I never know if I will be able to sit in the seat that I selected when I purchased the ticket or if I will be told by Customer Service (!!!) that I must relocate from first class to a seat in the back of the aircraft with no explanation (both happened to me this week). Will the food be frozen and half defrosted, or scalding hot? Will the drinks be warm? Will the flight attendants be surly and mean? Will the toilets be cramped and foul? Will the seats be narrow and uncomfortable? Will there be a real electric outlet at the seat, or just an unreliable USB-2 port? Will there be enough seats in the boarding lounge or just a few? Will the boarding process be smooth and efficient, or will the gate agents mess it up and delay it needlessly for 30 or 40 minutes? Will the catering and cleaning crew be prompt or will they take an extra 30 minutes? Will the brakes on the aircraft work properly, or will the pilot delay takeoff for four hours while the ground crew attends to what can only be described as routine maintenance that should have been done the night before? I've eexperienced every one of these unpleasant things this year, 2026. The only thing I can reliably count on is that American will find a new way to make the experience of flying as miserable as they possibly can.

Flight was fine, but not having WiFi was a major negative

When I booked my flight a month ago - I selected a seat. That seat was NOT the one I ended up with when I checked into my flight the day before. This is the second time this has occurred. So, I checked my next flight on Wednesday and Thursday and no seat was assigned. Poor, very poor customer service.

Traveling to a place near Madison?

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

Everything you need to know for your flight to Madison

Information on the airport you'll fly into in Madison