Greater Antilles Cheap Holidays

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Price found within the past 48 hours. Click for updated prices.
The Condado Plaza Hotel

The Condado Plaza Hotel

Condado
€865
per person
24 Sept - 29 Sept
found 1 day ago
Return flight included
Chicago (ORD) to San Juan (SJU)
8/10 Very good! (2,651 reviews)
Jesus was spectacular

Reviewed on 10 Aug 2026

Hyatt Regency Grand Reserve Puerto Rico

Hyatt Regency Grand Reserve Puerto Rico

Zarzal
€988
per person
24 Sept - 29 Sept
found 1 day ago
Return flight included
Chicago (ORD) to San Juan (SJU)
9/10 Wonderful! (3,176 reviews)
DoubleTree by Hilton San Juan

DoubleTree by Hilton San Juan

Santurce
€892
per person
24 Sept - 29 Sept
found 1 day ago
Return flight included
Chicago (ORD) to San Juan (SJU)
9/10 Wonderful! (1,015 reviews)
.

Reviewed on 9 Aug 2026

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

Mameyes II
€1,012
per person
24 Sept - 29 Sept
found 1 day ago
Return flight included
Chicago (ORD) to San Juan (SJU)
8.6/10 Excellent! (2,188 reviews)
El resort muy l

Reviewed on 9 Aug 2026

Marriott Isla Verde Beach Resort

Marriott Isla Verde Beach Resort

Isla Verde
€1,030
per person
24 Sept - 29 Sept
found 1 day ago
Return flight included
Chicago (ORD) to San Juan (SJU)
8.8/10 Excellent! (2,103 reviews)
I

Reviewed on 10 Aug 2026

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Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

Mameyes II
€1,012
per person
24 Sept - 29 Sept
found 1 day ago
Return flight included
Chicago (ORD) to San Juan (SJU)
8.6/10 Excellent! (2,188 reviews)
El resort muy l

Reviewed on 9 Aug 2026

Don't see what you're looking for?
See all available trips from Chicago to Greater Antilles
View all trips
Casa del Caribe Inn

Casa del Caribe Inn

57 Caribe Street San Juan
Stay at this guesthouse 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. ...
Casa del Caribe Inn
Coral by the Sea Hotel

Coral by the Sea Hotel

Calle Rosa 2 Carolina
Stay at this hotel in Carolina. Enjoy free Wi-Fi, 2 restaurants and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ...
6.4/10 (2,430 reviews)
"This hotel is only good for the location and perhaps one night. For what I paid for the room it should be a whole lot nicer. The property is very dated and not upgraded. The staff was pleasant nobody was overly nice."

Reviewed on 9 Aug 2026

Coral by the Sea Hotel
Ciqala Suites Hotel

Ciqala Suites Hotel

752 Manuel Fernandez Juncos Ave San Juan
Stay at this business-friendly hotel in San Juan. Enjoy free Wi-Fi, free parking and a rooftop terrace. Our guests praise the breakfast and the helpful staff ...
8.2/10 Very good! (1,013 reviews)
"Staff was great. Breakfast taken to the room excellent. Loved the rooftop restaurant. Room was clean, comfortable, huge bathroom, only downfall was the sofa bed mattress needs to be updated"

Reviewed on 10 Aug 2026

Ciqala Suites Hotel
See all 39,907 properties in Greater Antilles
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.