Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Madison to Caribbean Islands from $207

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Madison to Caribbean Islands departing on 3/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

Find the cheapest flights from Madison to Caribbean Islands

Cheap round-trip flights

These are some of the best round-trip flight deals from Madison to Caribbean Islands that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Madison to Caribbean Islands.

Cheap last minute flights

Planning a quick getaway from Madison to Caribbean Islands? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Caribbean Islands, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Madison to Caribbean Islands

Find recent round-trip train or bus tickets from Madison to Caribbean Islands.

All round-trip flight deals to Caribbean Islands

The cheapest plane tickets to Caribbean Islands found on KAYAK recently.
5:30 am - 10:07 pmMSN-SJU
14h 37m2 stops
2:25 pm - 11:50 pmSJU-MSN
11h 25m2 stops
$263American Airlines
Find Deal
Tue, Jan 21 - Thu, Jan 23
5:30 am - 10:07 pmMSN-SJU
14h 37m2 stops
8:05 am - 11:50 pmSJU-MSN
17h 45m1 stop
$264American Airlines
Find Deal
Tue, Jan 21 - Thu, Jan 23
6:35 am - 4:24 pmMSN-SJU
7h 49m1 stop
4:25 pm - 10:39 pmSJU-MSN
8h 14m1 stop
$288Delta
Find Deal
Sat, Jan 11 - Tue, Jan 14
7:00 am - 3:50 pmMSN-SJU
6h 50m1 stop
4:25 pm - 10:39 pmSJU-MSN
8h 14m1 stop
$311Delta
Find Deal
Wed, Jan 1 - Tue, Jan 14
6:30 am - 10:22 pmMSN-SJU
13h 52m2 stops
2:05 am - 11:54 amSJU-MSN
11h 49m2 stops
$354United Airlines
Find Deal
Sun, Jan 12 - Mon, Jan 13
12:40 pm - 12:36 amMSN-SJU
9h 56m2 stops
2:05 am - 11:54 amSJU-MSN
11h 49m2 stops
$399United Airlines
Find Deal
Tue, Jan 21 - Wed, Jan 22
5:46 pm - 3:45 pmMSN-PUJ
19h 59m2 stops
4:50 pm - 9:08 amPUJ-MSN
18h 18m2 stops
Sat, Jan 11 - Fri, Jan 17
3:59 pm - 1:49 amMSN-SJU
8h 50m1 stop
5:45 am - 2:59 pmSJU-MSN
10h 14m1 stop
$414Frontier
Find Deal
Mon, Mar 10 - Mon, Mar 17
7:10 pm - 12:57 amMSN-SJU
27h 47m3 stops
9:34 pm - 5:36 pmSJU-MSN
22h 02m2 stops
Sun, Feb 9 - Fri, Feb 14
3:59 pm - 1:49 amMSN-SJU
8h 50m1 stop
5:45 am - 6:18 pmSJU-MSN
13h 33m1 stop
$546Frontier
Find Deal
Mon, Mar 10 - Sat, Mar 15
3:59 pm - 1:49 amMSN-SJU
8h 50m1 stop
$207Frontier
Find Deal
Mon, Mar 17
5:30 am - 5:41 pmMSN-STT
10h 11m2 stops
$277American Airlines
Find Deal
Tue, Jan 21
4:24 pm - 10:15 amMSN-MBJ
16h 51m1 stop
$336American Airlines
Find Deal
Fri, Feb 14
6:15 am - 8:43 pmMSN-SJU
13h 28m2 stops
$362United Airlines
Find Deal
Mon, Mar 17
6:15 am - 9:22 pmMSN-SJU
14h 07m2 stops
$373United Airlines
Find Deal
Mon, Mar 17
6:15 am - 9:22 pmMSN-SJU
14h 07m3 stops
$426United Airlines
Find Deal
Mon, Mar 17
5:25 pm - 3:40 pmMSN-STT
20h 15m1 stop
$462United Airlines
Find Deal
Tue, Jan 21
6:15 am - 9:22 pmMSN-SJU
14h 07m3 stops
$465United Airlines
Find Deal
Mon, Mar 17
6:30 am - 1:56 pmMSN-STT
29h 26m3 stops
$483United Airlines
Find Deal
Tue, Jan 21
1:25 pm - 2:49 amMSN-SDQ
11h 24m1 stop
7:05 am - 3:18 pmSDQ-MSN
10h 13m1 stop
$673Delta
Find Deal
Tue, Dec 24 - Tue, Jan 7
1:10 pm - 2:49 amMSN-SDQ
11h 39m1 stop
7:05 am - 3:18 pmSDQ-MSN
10h 13m1 stop
$743Delta
Find Deal
Wed, Dec 25 - Tue, Jan 7
6:21 am - 5:00 pmMSN-PUJ
8h 39m1 stop
5:40 pm - 10:12 amPUJ-MSN
18h 32m1 stop
$786American Airlines
Find Deal
Mon, Dec 23 - Wed, Jan 8
5:18 pm - 12:14 pmMSN-PUJ
16h 56m2 stops
5:40 pm - 10:12 amPUJ-MSN
18h 32m1 stop
$791American Airlines
Find Deal
Mon, Dec 23 - Wed, Jan 8
5:47 am - 2:25 pmMSN-PUJ
6h 38m1 stop
3:29 pm - 10:39 pmPUJ-MSN
9h 10m1 stop
$805Delta
Find Deal
Mon, Dec 23 - Tue, Jan 7
3:50 pm - 4:15 pmMSN-PUJ
22h 25m2 stops
3:15 pm - 3:15 pmPUJ-MSN
26h 00m2 stops
$1,245United Airlines
Find Deal
Sun, Dec 22 - Sun, Jan 5
10:51 am - 10:55 amMSN-NAS
23h 04m2 stops
11:30 am - 3:15 pmNAS-MSN
28h 45m3 stops
$1,382
Find Deal
Tue, Dec 24 - Thu, Dec 26
6:19 am - 4:25 pmMSN-GCM
33h 06m2 stops
6:00 pm - 3:15 pmGCM-MSN
22h 15m2 stops
$1,406United Airlines
Find Deal
Thu, Dec 26 - Sat, Jan 4
6:40 pm - 7:25 amMSN-SDQ
34h 45m3 stops
2:00 pm - 2:55 pmSDQ-MSN
26h 55m3 stops
$1,508
Find Deal
Tue, Dec 24 - Sun, Jan 5
12:15 pm - 4:15 pmMSN-SXM
26h 00m2 stops
4:55 pm - 9:17 pmSXM-MSN
30h 22m2 stops
$3,423Air Canada
Find Deal
Sun, Dec 22 - Sun, Jan 5

American Airlines flights from Madison to Caribbean Islands

Our best American Airlines deals on Madison to Caribbean Islands flight tickets
American Airlines
Jan 21
MSN5:30 amMadison Truax Field
14h 37m
2 stops
SJU10:07 pmSan Juan Luis Munoz Marin Intl
Jan 23
SJU2:25 pmSan Juan Luis Munoz Marin Intl
11h 25m
2 stops
MSN11:50 pmMadison Truax Field
American Airlines
Jan 21
MSN5:30 amMadison Truax Field
14h 37m
2 stops
SJU10:07 pmSan Juan Luis Munoz Marin Intl
Jan 23
SJU8:05 amSan Juan Luis Munoz Marin Intl
17h 45m
1 stop
MSN11:50 pmMadison Truax Field
American Airlines
Jan 21
MSN11:43 amMadison Truax Field
10h 15m
1 stop
SJU11:58 pmSan Juan Luis Munoz Marin Intl
Jan 28
SJU12:50 pmSan Juan Luis Munoz Marin Intl
10h 20m
2 stops
MSN9:10 pmMadison Truax Field

Delta flights from Madison to Caribbean Islands

Our best Delta deals on Madison to Caribbean Islands flight tickets
Delta
Jan 11
MSN6:35 amMadison Truax Field
7h 49m
1 stop
SJU4:24 pmSan Juan Luis Munoz Marin Intl
Jan 14
SJU4:25 pmSan Juan Luis Munoz Marin Intl
8h 14m
1 stop
MSN10:39 pmMadison Truax Field
Delta
Jan 1
MSN7:00 amMadison Truax Field
6h 50m
1 stop
SJU3:50 pmSan Juan Luis Munoz Marin Intl
Jan 14
SJU4:25 pmSan Juan Luis Munoz Marin Intl
8h 14m
1 stop
MSN10:39 pmMadison Truax Field
Delta
Feb 25
MSN7:00 amMadison Truax Field
14h 46m
2 stops
SJU11:46 pmSan Juan Luis Munoz Marin Intl
Mar 3
SJU4:10 pmSan Juan Luis Munoz Marin Intl
8h 32m
1 stop
MSN10:42 pmMadison Truax Field

See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Madison to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Caribbean Islands?

The month of August is, on average, the cheapest month to fly to Caribbean Islands from Madison, with most prices found around $399. The month of January is another great option to travel to Caribbean Islands, with average flight prices from Madison averaging around $464.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Madison to Caribbean Islands is on a Monday. Travelers who choose to depart for Caribbean Islands on a Monday will often find tickets for as low as $494. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $609. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the afternoon. momondo users have found flights departing from Madison to Caribbean Islands in the afternoon for as low as $370. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets at noon because they tend to be around $701. Of course, these prices can vary depending on the time of year and what airport you fly to.

How far in advance should I book a flight to Caribbean Islands?

The ideal time to book your flight to Caribbean Islands is 57 days in advance when prices tend to average $540. Keep in mind that you might be able to find cheaper flights to Caribbean Islands at any time. In fact, our users found flights for as low as $264 in the past 72 hours.

Can stopping save me money on Madison to Caribbean Islands flights?

You could potentially save up to 20% on your flight if you consider stops on a Madison to Caribbean Islands flight.

Cheap Madison to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to Caribbean Islands

Best Price Found

$207

Fastest flight time

5h 43m

Direct flights

None

Airports in Caribbean Islands

7 airports
The best one-way flight to Caribbean Islands from Madison in the past 72 hours is $207. The best round-trip flight deal from Madison to Caribbean Islands found on momondo in the last 72 hours is $263.
The fastest flight from Madison to Caribbean Islands takes 5h 43m
There are no direct flights from Madison to Caribbean Islands. Popular non-direct routes for this connection are Madison Truax Field Airport - Saint Thomas Island Cyril E King Airport, Madison Truax Field Airport - San Juan Luis Munoz Marin Intl Airport and Madison Truax Field Airport - Montego Bay Sangster Intl Airport.
There are 7 airports near Caribbean Islands: George Town Owen Roberts Intl (GCM), Santo Domingo Las Americas (SDQ), Saint Thomas Island Cyril E King (STT), Montego Bay Sangster Intl (MBJ), Punta Cana (PUJ), Simpson Bay Princess Juliana (SXM), San Juan Luis Munoz Marin Intl (SJU)

  • When did momondo last update prices for flights from Madison Truax Field Airport to Caribbean Islands?

    Prices for flights from Madison Truax Field Airport to Caribbean Islands are updated daily.

  • How many operators does momondo search for flights from Madison Truax Field Airport to Caribbean Islands?

  • How old do you have to be to fly from Madison Truax Field Airport to Caribbean Islands?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Madison Truax Field Airport to Caribbean Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

    The necessary travel and health documents for your Caribbean Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Madison to Caribbean Islands?


Best airlines flying from Madison to Caribbean Islands

Compare and see reviews for airlines that fly from Madison to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $234Free CancellationRating
6.1
3,474 reviews
Search Frontier flights
DeltaPriceFrom $284Free CancellationRating
8.0
8,597 reviews
Search Delta flights
American AirlinesPriceFrom $335Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $358Free CancellationRating
7.4
9,039 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Madison to Caribbean Islands?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Madison to Caribbean Islands. momondo saves you time and could save you money on your trip.

Can I find flights from Madison to Caribbean Islands with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Madison to Caribbean Islands flights to just show those with flexible booking policies.

How can momondo help me find flights from Madison to Caribbean Islands?

Once all potential Madison to Caribbean Islands flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Madison to Caribbean Islands right now. Can momondo alert me if prices change?

Price alerts on flights to Caribbean Islands from Madison are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Thu 12/26
Thu 1/2
Email me momondo's favorite deals

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Popular flights according to clicks in the last 7 days on momondo