Find Cheap Flights to Caribbean

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Madison Truax Field to Caribbean

(Round-trip)
Depart: Tue Oct 3 2017 Return: Wed Oct 4 2017 Trip spans 2 days
American Airlines
American Airlines
MSN
SJU
9h 31m
2 stops
SJU
MSN
12h 59m
2 stops
Depart: Sat Sep 30 2017 Return: Tue Oct 3 2017 Trip spans 4 days
United
United
MSN
SJU
16h 27m
2 stops
SJU
MSN
21h 07m
2 stops
Depart: Sat Jan 13 2018 Return: Sat Jan 20 2018 Trip spans 8 days
Delta
Delta
MSN
SXM
8h 44m
1 stop
SXM
MSN
18h 17m
1 stop
Depart: Thu Dec 28 2017 Return: Fri Dec 29 2017 Trip spans 2 days
Multiple Airlines
Multiple Airlines
MSN
PUJ
20h 58m
1 stop
PUJ
MSN
18h 57m
2 stops
Depart: Wed Jan 24 2018 Return: Sat Feb 3 2018 Trip spans 11 days
American Airlines
American Airlines
MSN
SJU
6h 43m
1 stop
SJU
MSN
11h 10m
2 stops
Depart: Tue Feb 13 2018 Return: Thu Feb 22 2018 Trip spans 10 days
United
United
MSN
SJU
15h 50m
2 stops
SJU
MSN
11h 31m
2 stops
Depart: Mon Sep 11 2017 Return: Mon Sep 18 2017 Trip spans 8 days
United
United
MSN
SJU
19h 42m
2 stops
SJU
MSN
7h 24m
1 stop
Depart: Tue Feb 6 2018 Return: Tue Feb 13 2018 Trip spans 8 days
American Airlines
American Airlines
MSN
PUJ
20h 18m
2 stops
PUJ
MSN
15h 16m
2 stops
Depart: Sat Nov 4 2017 Return: Sat Nov 11 2017 Trip spans 8 days
United
United
MSN
SJU
17h 05m
2 stops
SJU
MSN
12h 44m
2 stops
Depart: Fri Dec 1 2017 Return: Fri Dec 8 2017 Trip spans 8 days
American Airlines
American Airlines
MSN
AUA
20h 04m
2 stops
AUA
MSN
21h 06m
2 stops
Depart: Fri Nov 3 2017 Return: Sat Nov 11 2017 Trip spans 9 days
United
United
MSN
SJU
16h 32m
2 stops
SJU
MSN
12h 44m
2 stops
Depart: Tue Aug 29 2017 Return: Sun Sep 3 2017 Trip spans 6 days
American Airlines
American Airlines
MSN
SJU
10h 39m
1 stop
SJU
MSN
8h 45m
1 stop
Depart: Sat Oct 7 2017 Return: Sun Oct 15 2017 Trip spans 9 days
Delta
Delta
MSN
SXM
18h 33m
2 stops
SXM
MSN
8h 32m
1 stop
Depart: Sun Nov 5 2017 Return: Sat Nov 11 2017 Trip spans 7 days
United
United
MSN
SJU
28h 20m
1 stop
SJU
MSN
12h 44m
2 stops
Depart: Tue Oct 31 2017 Return: Sat Nov 4 2017 Trip spans 5 days
American Airlines
American Airlines
MSN
STT
12h 43m
2 stops
STT
MSN
9h 01m
2 stops
Depart: Thu Nov 23 2017 Return: Mon Nov 27 2017 Trip spans 5 days
Delta
Delta
MSN
GCM
6h 46m
1 stop
GCM
MSN
20h 27m
2 stops
Depart: Thu Jan 4 2018 Return: Tue Jan 9 2018 Trip spans 6 days
United
United
MSN
SJU
8h 05m
1 stop
SJU
MSN
20h 24m
2 stops
Depart: Tue Nov 14 2017 Return: Mon Nov 20 2017 Trip spans 7 days
American Airlines
American Airlines
MSN
NAS
5h 34m
1 stop
NAS
MSN
7h 50m
1 stop
Depart: Fri Jan 19 2018 Return: Sun Jan 21 2018 Trip spans 3 days
American Airlines
American Airlines
MSN
NAS
5h 20m
1 stop
NAS
MSN
7h 36m
1 stop
Depart: Fri Oct 27 2017 Return: Mon Oct 30 2017 Trip spans 4 days
American Airlines
American Airlines
MSN
SJU
7h 39m
1 stop
SJU
MSN
7h 26m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

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please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Madison
$450
Destination

Nassau
$569
San Juan
$450
Saint Thomas Island
$541
Simpson Bay
$698
Oranjestad
$524
George Town
$752
Punta Cana
$494