When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 19 days in advance, which can save you up to 115% on flights from Caribbean Islands to Madison compared to booking the week you need them. Waiting 19 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $546. For sooner than that we have options available in the next 3 days from $694.
September is one of the best times of the year to fly to Madison from Caribbean Islands. Prices for September average $507 per person but you can even find prices for as low as $297. The most expensive prices can be found in the month of June. Opting for a September flight can save you 29% on your journey compared to booking in June
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean Islands to Madison as you normally would.
Fly from
Fly to
Budget
$331 - $519
Route
Depart
Return
Price
San Juan Luis Munoz Marin IntlMadison Truax Field
SJU - MSN
SJUMSN
San Juan Luis Munoz Marin Intl
Tue 8/27
1 stop15h 19m
Madison Truax Field
Sat 9/7
2 stops15h 33m
San Juan Luis Munoz Marin IntlMadison Truax Field
SJU - MSN
SJUMSN
San Juan Luis Munoz Marin Intl
Tue 8/27
2 stops9h 59m
Madison Truax Field
Sat 9/7
2 stops11h 57m
San Juan Luis Munoz Marin IntlMadison Truax Field
SJU - MSN
SJUMSN
San Juan Luis Munoz Marin Intl
Sat 8/24
1 stop10h 48m
Madison Truax Field
Wed 8/28
1 stop9h 18m
San Juan Luis Munoz Marin IntlMadison Truax Field
SJU - MSN
SJUMSN
San Juan Luis Munoz Marin Intl
Sat 8/24
1 stop10h 48m
Madison Truax Field
Wed 8/28
1 stop9h 18m
Nassau IntlMadison Truax Field
NAS - MSN
NASMSN
Nassau Intl
Fri 9/20
1 stop10h 12m
Madison Truax Field
Tue 9/24
1 stop6h 23m
Montego Bay Sangster IntlMadison Truax Field
MBJ - MSN
MBJMSN
Montego Bay Sangster Intl
Thu 7/4
1 stop25h 50m
Madison Truax Field
Sat 8/31
2 stops18h 33m
Montego Bay Sangster IntlMadison Truax Field
MBJ - MSN
MBJMSN
Montego Bay Sangster Intl
Thu 7/4
1 stop22h 06m
Madison Truax Field
Sat 8/31
1 stop25h 18m
Montego Bay Sangster IntlMadison Truax Field
MBJ - MSN
MBJMSN
Montego Bay Sangster Intl
Wed 9/4
2 stops22h 59m
Madison Truax Field
Sat 9/7
2 stops19h 40m
San Juan Luis Munoz Marin IntlMadison Truax Field
SJU - MSN
SJUMSN
San Juan Luis Munoz Marin Intl
Mon 8/26
2 stops11h 46m
Madison Truax Field
Sat 9/7
1 stop7h 12m
No data available for this route at this time. Please check back soon.
Food
Boarding
Comfort
Entertainment
Crew
Overall
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Boarding
Comfort
Entertainment
Crew
Overall
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Boarding
Comfort
Entertainment
Crew
Overall
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Boarding
Comfort
Entertainment
Crew
Overall
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Boarding
Comfort
Entertainment
Crew
Overall
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
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