Greater Antilles Cheap Holidays
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Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Grand Reserve Puerto Rico
Zarzal
Price was €1,590, price is now €924 per person
€924
per person
20 Jan - 26 Jan
found 1 day ago
Return flight included
Chicago (ORD) to San Juan (SJU)
9/10 Wonderful! (2,764 reviews)
Staff was amazing. The room was impeccable. The amenities where on point couldn’t have asked for a better vacation
Reviewed on 30 Nov 2025
Bahia Principe Luxury Ambar - Adults Only - All Inclusive
Bávaro
Price was €2,785, price is now €1,474 per person
€1,474
per person
3 Jan - 9 Jan
found 1 day ago
Return flight included
Miami (MIA) to Punta Cana (PUJ)
9/10 Wonderful! (2,437 reviews)
The staff was amazing. Always smiling and friendly and offering to help you. Very nice relaxed Hotel.
Reviewed on 1 Dec 2025
Barceló Bávaro Palace - All Inclusive
Bávaro
Price was €2,102, price is now €1,166 per person
€1,166
per person
3 Jan - 9 Jan
found 1 day ago
Return flight included
Miami (MIA) to Punta Cana (PUJ)
8/10 Very Good! (5,390 reviews)
Room was great super comfortable and clean. Staff was superb. Great amenities fun for all ages.
Reviewed on 2 Dec 2025
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
Mameyes II
Price was €1,965, price is now €1,294 per person
€1,294
per person
20 Jan - 26 Jan
found 1 day ago
Return flight included
Chicago (ORD) to San Juan (SJU)
8.6/10 Excellent! (2,206 reviews)
They exceeded my expectations.
No complaints except the food is too costly.
Reviewed on 1 Dec 2025
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Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
Mameyes II
Price was €1,965, price is now €1,294 per person
€1,294
per person
20 Jan - 26 Jan
found 1 day ago
Return flight included
Chicago (ORD) to San Juan (SJU)
8.6/10 Excellent! (2,206 reviews)
They exceeded my expectations.
No complaints except the food is too costly.
Reviewed on 1 Dec 2025
Don't see what you're looking for?
See all available trips from Chicago to Greater Antilles
View all tripsPrice found within the past 48 hours. Click for updated prices.
Barceló Bávaro Palace - All Inclusive
Bávaro
Price was €1,470, price is now €989 per person
€989
per person
16 Jan - 19 Jan
found 20 hours ago
Return flight included
New York (NYC) to Punta Cana (PUJ)
8/10 Very Good! (5,390 reviews)
Room was great super comfortable and clean. Staff was superb. Great amenities fun for all ages.
Reviewed on 2 Dec 2025
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Ciqala Suites Hotel
Santurce
Price was €619, price is now €446 per person
€446
per person
26 Jan - 29 Jan
found 24 hours ago
Return direct flight included
Los Angeles (LAX) to San Juan (SJU)
7.8/10 Good! (1,003 reviews)
Everything was amazing. We are booking our next weekend getaway and staying in Ciqala again!
Reviewed on 23 Nov 2025
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
Mameyes II
Price was €1,008, price is now €742 per person
€742
per person
26 Jan - 29 Jan
found 24 hours ago
Return direct flight included
Los Angeles (LAX) to San Juan (SJU)
8.6/10 Excellent! (2,206 reviews)
They exceeded my expectations.
No complaints except the food is too costly.
Reviewed on 1 Dec 2025
Hyatt Place Bayamon
Hato Tejas
Price was €621, price is now €463 per person
€463
per person
26 Jan - 29 Jan
found 24 hours ago
Return direct flight included
Los Angeles (LAX) to San Juan (SJU)
9/10 Wonderful! (1,504 reviews)
The staff was wonderful! We had nice conversations with some of the staff. They were helpful when I asked questions.
Reviewed on 1 Dec 2025
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Coral by the Sea Hotel
Calle Rosa 2 Carolina
Stay at this hotel in Carolina. Enjoy free Wi-Fi, 2 restaurants and parking (surcharge). Our guests praise the helpful staff and the clean rooms in their reviews. ...
6/10 (1,973 reviews)
Very generous and friendly
Reviewed on 29 Nov 2025
Casa del Caribe Inn
57 Caribe St., Condado San Juan
Stay at this inn in San Juan. Enjoy free Wi-Fi, daily housekeeping and a garden. Our guests praise the helpful staff and the clean rooms in their reviews. Popular ...
7/10 Good! (1,011 reviews)
It was very awesome. The staff was very helpful and went out of their way to make it a pleasant stay. The room was very clean and comfortable. I have already made my reservations for next year.
Reviewed on 28 Nov 2025
Ciqala Suites Hotel
752 Manuel Fernandez Juncos Ave San Juan
Stay at this business-friendly hotel in San Juan. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
7.6/10 Good! (1,009 reviews)
Clean room, looks like pictures online, friendly staff. Rooftop can get a little loud on weekend but its quiet during the week. Great location. Recommend!
Reviewed on 24 Nov 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
