Greater Antilles Luxury Holidays
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Price found within the past 48 hours. Click for updated prices.
Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - All Inclusive
€1,458
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
Chicago (ORD) to Montego Bay (MBJ)
8.4/10 Very good! (2,452 reviews)
Check-in was long, grueling and disorganized.
Reviewed on 9 Aug 2026
Moon Palace Jamaica – All Inclusive
€1,899
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
Chicago (ORD) to Montego Bay (MBJ)
8.4/10 Very good! (2,086 reviews)
Well worth it …. There wa. So much to do for both adults and kids… we needed more time to enjoy it all…. Staff was very polite, food was amazing … we had an amazing vacation.
Reviewed on 9 Aug 2026
Grand Palladium Lady Hamilton Resort & Spa All Inclusive
€1,836
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
Chicago (ORD) to Montego Bay (MBJ)
8/10 Very good! (1,405 reviews)
Staff at reception needs to be better trained to be much more efficient in checking in guests. Our checking in experience was very rough.
Reviewed on 9 Aug 2026
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See all available trips from Chicago to Greater Antilles
View all tripsPrice found within the past 48 hours. Click for updated prices.
Moon Palace Jamaica – All Inclusive
€1,899
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
Chicago (ORD) to Montego Bay (MBJ)
8.4/10 Very good! (2,086 reviews)
Well worth it …. There wa. So much to do for both adults and kids… we needed more time to enjoy it all…. Staff was very polite, food was amazing … we had an amazing vacation.
Reviewed on 9 Aug 2026
Grand Palladium Lady Hamilton Resort & Spa All Inclusive
€1,836
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
Chicago (ORD) to Montego Bay (MBJ)
8/10 Very good! (1,405 reviews)
Staff at reception needs to be better trained to be much more efficient in checking in guests. Our checking in experience was very rough.
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
Condado Vanderbilt Hotel
1055 Ashford Avenue San Juan
Stay at this luxury hotel in San Juan. Enjoy free Wi-Fi, 4 outdoor pools and a full-service spa. Our guests praise the helpful staff and the clean rooms in their ...
Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - All Inclusive
Salt Coppers Runaway Bay Saint Ann
Stay at this luxury resort in Runaway Bay. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the pool and the helpful staff in their reviews. ...
8.4/10 Very good! (2,466 reviews)
"Check-in was long, grueling and disorganized."
Reviewed on 9 Aug 2026
Majestic Elegance Punta Cana - All Inclusive
Playa Bavaro - Punta Cana Punta Cana La Altagracia
Stay at this luxury resort in Punta Cana. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the pool and the restaurant in their reviews. ...
9/10 Wonderful! (4,958 reviews)
"Room clean hood enough for 3 stars. Staff does not understand english. Swim up bar was good. I would give 4 stars The pools need to maintenance The food litle salty Tennis courts and pickleball courts. Need to play early morning or afternoon after 5pm. Because the sun. Italy, Japanese and steak house ..."
Reviewed on 9 Aug 2026
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.
