$203 Find Cheap Flights from Caribbean Islands to Madison - Compare and Save

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 7/8. 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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Cheap Flights from Caribbean Islands to Madison

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean Islands 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 Islands to Madison

Thu, Sep 17 - Mon, Sep 21
Delta Logo
7:00 am - 9:15 pm
SJU
-
MSN
15h 15m
2 stops
Delta Logo
6:00 am - 1:16 pm
MSN
-
SJU
6h 16m
1 stop
$256Delta
Mon, Sep 14 - Tue, Sep 22
Multiple Airlines Logo
6:31 pm - 4:00 pm
SJU
-
MSN
22h 29m
1 stop
Multiple Airlines Logo
4:40 pm - 1:50 am
MSN
-
SJU
8h 10m
1 stop
$341Multiple Airlines
Thu, Sep 17 - Mon, Sep 21
Delta Logo
7:30 am - 4:18 pm
SJU
-
MSN
9h 48m
1 stop
Delta Logo
6:00 am - 1:16 pm
MSN
-
SJU
6h 16m
1 stop
$357Delta
Mon, Sep 14 - Tue, Sep 22
American Airlines Logo
10:16 am - 7:46 pm
SJU
-
MSN
10h 30m
2 stops
American Airlines Logo
8:05 pm - 2:50 pm
MSN
-
SJU
17h 45m
2 stops
$366American Airlines
Wed, Sep 30 - Sat, Oct 3
United Airlines Logo
3:56 pm - 10:35 pm
SJU
-
MSN
7h 39m
1 stop
United Airlines Logo
5:00 am - 2:44 pm
MSN
-
SJU
8h 44m
1 stop
$381United Airlines
Wed, Jul 8 - Tue, Jul 14
American Airlines Logo
7:00 am - 9:41 pm
SJU
-
MSN
15h 41m
1 stop
American Airlines Logo
7:00 am - 10:59 pm
MSN
-
SJU
14h 59m
1 stop
$406American Airlines
Mon, Sep 14 - Mon, Oct 19
American Airlines Logo
2:22 pm - 11:24 pm
SJU
-
MSN
10h 02m
1 stop
American Airlines Logo
8:25 pm - 1:45 pm
MSN
-
SJU
16h 20m
1 stop
$409American Airlines
Tue, Sep 29 - Sat, Oct 3
United Airlines Logo
1:00 am - 1:37 pm
SJU
-
MSN
13h 37m
2 stops
United Airlines Logo
6:42 am - 8:38 pm
MSN
-
SJU
12h 56m
2 stops
$430United Airlines
Wed, Jul 8 - Tue, Jul 14
American Airlines Logo
7:00 am - 9:41 pm
SJU
-
MSN
15h 41m
1 stop
American Airlines Logo
6:00 am - 6:24 pm
MSN
-
SJU
11h 24m
2 stops
$449American Airlines
Fri, Aug 21 - Tue, Aug 25
United Airlines Logo
7:00 am - 8:53 pm
SJU
-
MSN
14h 53m
2 stops
United Airlines Logo
6:30 am - 2:44 pm
MSN
-
SJU
7h 14m
1 stop
$451United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$203
Best time to beat the crowds but there is an average 38% 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 Islands to Madison

  • How does KAYAK find such low prices on flights from Caribbean Islands 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 Islands to Madison.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean Islands to Madison?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Madison from Caribbean Islands 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 Islands 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 Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands 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 Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Caribbean Islands to Madison

 
Need help choosing which airline to fly with from Caribbean Islands 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.
7.1
American AirlinesOverall score based on 11670 reviews
6.4Food
7.5Boarding
6.8Entertainment
7.2Comfort
7.9Crew
Airline reviews

We sat on plane at gate delayed without communication as to why we were just sitting there

4.0 OkayMICHAEL, Jun 2026
MIA - TPA
Read more American Airlines reviews

We sat on plane at gate delayed without communication as to why we were just sitting there

Agency very bad had to cancelled my booking too many changes in the flight changed my flight to 1 week

Trash. Sat on the runway for 40 mins…missed connecting flight because of it now I’m stuck. Thanks…a whole fkn lot.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The plane was comfortable but the crew wasn’t friendly.

Awfully rude American worker at door when we started boarding flight. Then, walk into a blazing hot airplane with no air conditioning until twenty minutes into the flight. Free entertainment was non existent! My husband, along with the fellow passenger in our row, and I could not get entertainment to work, no WIFI! Really?? Been flying American a long time. Was very disappointed.

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

Leave on time. We waited on the plane for hour hours and it was hot and smelly

Check in was easy. Flights were smooth. Flight attendants were courteous and friendly.

Two hours delay, probably one hour because they didn’t bring catering and they had to bring water in board. There a change of aircraft. But delays galore at CLT so it must be a CLT and/or AA operation issue. The 1 hr additional delays because nobody could bring 2 packs of water sooner is probably the best example of this airline operates

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