Cheap Flights To Caribbean

Choose two or more items and save on your trip:

Caribbean Flights as Low as $208

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Oct 7 - Wed, Oct 15
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$208 Roundtrip, found 20 hours ago
$208
Roundtrip
found 20 hours ago
Select Spirit Airlines flight, departing Tue, Oct 7 from O'Hare Intl. to Luis Munoz Marin Intl., returning Wed, Oct 15, priced at $208 found 20 hours ago
Frontier Airlines
Sat, Oct 11 - Sun, Oct 19
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$304 Roundtrip, found 3 hours ago
$304
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Oct 11 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sun, Oct 19, priced at $304 found 3 hours ago
JetBlue Airways
Sun, Feb 8 - Fri, Feb 13
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$308 Roundtrip, found 3 days ago
$308
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Sun, Feb 8 from O'Hare Intl. to Luis Munoz Marin Intl., returning Fri, Feb 13, priced at $308 found 3 days ago
Spirit Airlines
Fri, Sep 19 - Wed, Sep 24
ORD
O'Hare Intl.
MBJ
Sir Donald Sangster Intl.
$327 Roundtrip, found 2 days ago
$327
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Sir Donald Sangster Intl., returning Wed, Sep 24, priced at $327 found 2 days ago
World Ticket Ltd
Wed, Feb 11 - Sat, Feb 21
ORD
O'Hare Intl.
PUJ
Punta Cana Intl.
$377 Roundtrip, found 21 hours ago
$377
Roundtrip
found 21 hours ago
Select World Ticket Ltd flight, departing Wed, Feb 11 from O'Hare Intl. to Punta Cana Intl., returning Sat, Feb 21, priced at $377 found 21 hours ago
Spirit Airlines
Sat, Oct 4 - Sat, Oct 18
ORD
O'Hare Intl.
AUA
Queen Beatrix Intl.
$400 Roundtrip, found 6 days ago
$400
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Sat, Oct 4 from O'Hare Intl. to Queen Beatrix Intl., returning Sat, Oct 18, priced at $400 found 6 days ago
American Airlines
Sun, Oct 12 - Fri, Oct 17
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$415 Roundtrip, found 3 hours ago
$415
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Sun, Oct 12 from O'Hare Intl. to Luis Munoz Marin Intl., returning Fri, Oct 17, priced at $415 found 3 hours ago
United
Fri, Dec 26 - Wed, Dec 31
ORD
O'Hare Intl.
POS
Piarco Intl.
$669 Roundtrip, found 1 day ago
$669
Roundtrip
found 1 day ago
Select United flight, departing Fri, Dec 26 from O'Hare Intl. to Piarco Intl., returning Wed, Dec 31, priced at $669 found 1 day ago

Caribbean Flights

For seniors in search of the best deals on airfares, AARP Travel Center Powered by Expedia features low-cost flights in Caribbean. Right here you may enter your expected travel dates to browse through the selection of cheap flights for seniors in Caribbean. The search engine presents a variety of low-cost plane tickets, airline carriers, and travel times to ensure the Caribbean AARP Travel Center flights suit your travel needs and preferences. And on top of affordable airline tickets, AARP members also enjoy no additional booking fees when you book your Caribbean senior flights on AARP Travel Center Powered by Expedia. These senior flights to or from Caribbean allow you to jet set without breaking the bank.