$166 Find Cheap Flights from Caribbean 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 11/10. 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.
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1 adult
Economy
0 bags
Round-trip
1 adult, Economy, 0 bags
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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.
Round-trip
One-way
Last minute
Recent round-trip flight deals from Caribbean to Madison
Wed, Nov 25 - Tue, Dec 1
2:05 am - 11:55 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
11h 50m2 stops Newark Chicago O'Hare Intl
5:30 am - 10:22 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
14h 52m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
$416United Airlines
Wed, Nov 25 - Tue, Dec 1
6:23 am - 9:40 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
17h 17m1 stop Dallas/Fort Worth
6:33 pm - 1:04 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
16h 31m1 stop Charlotte Douglas
$426American Airlines
Wed, Nov 25 - Tue, Dec 1
6:23 am - 4:55 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
12h 32m1 stop Dallas/Fort Worth
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
11:59 pm - 11:03 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
12h 04m1 stop Dallas/Fort Worth
11:35 am - 8:51 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
8h 16m1 stop Charlotte Douglas
$426American Airlines
Thu, Dec 10 - Sat, Jan 9
2:05 am - 2:50 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
14h 45m2 stops Newark Chicago O'Hare Intl
3:47 pm - 6:15 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
12h 28m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
$521United Airlines
Fri, Dec 11 - Sat, Jan 9
8:25 am - 2:50 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
8h 25m1 stop Chicago O'Hare Intl
2:55 pm - 6:15 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
13h 20m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
$521United Airlines
Thu, Dec 10 - Sun, Dec 13
8:25 am - 2:50 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
8h 25m1 stop Chicago O'Hare Intl
9:20 am - 12:36 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
13h 16m2 stops Chicago O'Hare Intl Newark
$591United Airlines
Sun, Nov 15 - Wed, Nov 18
7:23 am - 5:20 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
11h 57m1 stop Orlando
10:38 am - 1:25 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
24h 47m2 stops Tampa Fort Lauderdale
$714Multiple Airlines
Wed, Nov 18 - Sun, Nov 22
3:20 pm - 9:13 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
7h 53m1 stop Detroit Metropolitan Wayne County
5:30 am - 3:05 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
7h 35m1 stop Atlanta Hartsfield-Jackson
$731Delta
Sun, Nov 15 - Wed, Nov 18
7:23 am - 5:20 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
11h 57m1 stop Orlando
10:38 am - 7:27 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
30h 49m1 stop Tampa
$794Multiple Airlines
Recent one-way flight deals from Caribbean to Madison
Tue, Nov 10
8:45 am - 9:58 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
27h 13m2 stops Fort Lauderdale Tampa
$166Multiple Airlines
Fri, Nov 13
7:00 am - 9:58 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
28h 58m2 stops Fort Lauderdale Tampa
$197Multiple Airlines
Sat, Dec 5
1:18 pm - 11:09 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
11h 51m2 stops Miami Charlotte Douglas
$213American Airlines
Sat, Dec 5
7:20 am - 5:00 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
11h 40m2 stops Miami Dallas/Fort Worth
$213American Airlines
Sat, Dec 5
6:23 am - 11:36 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
7h 13m1 stop Charlotte Douglas
$213American Airlines
Thu, Feb 25
2:54 pm - 11:10 pmMBJ Montego Bay Sangster Intl-MSN Madison Truax Field
9h 16m1 stop Chicago O'Hare Intl
$257United Airlines
Wed, Feb 24
3:20 pm - 11:10 pmMBJ Montego Bay Sangster Intl-MSN Madison Truax Field
32h 50m2 stops Newark Chicago O'Hare Intl
$257United Airlines
Wed, Feb 24
1:25 pm - 9:37 pmMBJ Montego Bay Sangster Intl-MSN Madison Truax Field
9h 12m1 stop Newark
$257United Airlines
Fri, Nov 13
4:39 pm - 9:58 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
19h 19m1 stop Tampa
$267Multiple Airlines
Fri, Nov 13
7:00 am - 4:18 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
35h 18m3 stops Fort Lauderdale Raleigh-Durham Fort Myers SW Florida Intl
$272Multiple Airlines
Recent last minute flight deals from Caribbean to Madison
Wed, Nov 4 - Sat, Nov 7
3:17 pm - 11:00 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
9h 43m2 stops Miami Charlotte Douglas
9:15 am - 9:13 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
9h 58m2 stops Chicago O'Hare Intl Charlotte Douglas
$628American Airlines
Wed, Nov 4 - Sat, Nov 7
3:53 pm - 11:00 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
9h 07m1 stop Charlotte Douglas
12:23 pm - 9:13 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
6h 50m1 stop Charlotte Douglas
$628American Airlines
Wed, Nov 4 - Sat, Nov 7
7:45 am - 7:06 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
13h 21m2 stops New York John F Kennedy Intl Minneapolis St Paul
6:00 am - 4:10 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
8h 10m1 stop Minneapolis St Paul
$628Delta
Thu, Nov 5 - Mon, Nov 9
3:55 pm - 11:03 pmPUJ Punta Cana-MSN Madison Truax Field
9h 08m1 stop Atlanta Hartsfield-Jackson
5:30 am - 2:28 pmMSN Madison Truax Field-PUJ Punta Cana
6h 58m1 stop Atlanta Hartsfield-Jackson
$822Delta
Thu, Nov 5 - Mon, Nov 9
2:55 pm - 11:07 pmPUJ Punta Cana-MSN Madison Truax Field
10h 12m1 stop Chicago O'Hare Intl
5:00 am - 11:45 amMSN Madison Truax Field-PUJ Punta Cana
28h 45m2 stops Chicago O'Hare Intl Newark
$842United Airlines
Thu, Nov 5 - Mon, Nov 9
5:10 pm - 9:05 pmPUJ Punta Cana-MSN Madison Truax Field
29h 55m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl
7:00 pm - 5:28 pmMSN Madison Truax Field-PUJ Punta Cana
20h 28m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
$842United Airlines
Useful Info
Good to know
Low season
January
High season
April
Cheapest flight
$166
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.
1 person checking us as we boarded, left gate on time, 12.30 we are told we were held for 15 mins as other flights were waiting to take off, captain due to rain … they were having a longer gap between take offs , 3pm we took off , they went land route via New Orleans in to Florida landed at 5.45pm offered coffee and a biscuit
1 person checking us as we boarded, left gate on time, 12.30 we are told we were held for 15 mins as other flights were waiting to take off, captain due to rain … they were having a longer gap between take offs , 3pm we took off , they went land route via New Orleans in to Florida landed at 5.45pm offered coffee and a biscuit
Service was slow Flight was very loud at back of plane
There was no internet on the flight. As an executive flying during prime business hours, having internet is critical for a smooth experience. This impacted productivity and time that will need to be spent later to do the work I could have done on flight.
Terrible boarding - 4 flights boarded from the same gate. Chaos there; long ramps to the plane.
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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The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
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