Aruba
Grand Cayman
Dominican Republic

Introducing Nonstop Flights from Chicago and Newark to the Caribbean

 
Destinations served:
  • Punta Cana, Dominican Republic: Daily Nonstop, year-round service from Chicago and Newark
  • Aruba: Daily Nonstop, year-round service from Newark | Nonstop service on Saturday and Sunday from Chicago
  • Cayman Islands: Nonstop service on Saturdays from Chicago and Newark
All Deals Include: Round-trip airfare, Hotel accommodations, Taxes and more

Dominican Republic

Excellence El Carmen

Excellence El Carmen

This adults-only all-inclusive resort is set on a gorgeous golden sand beach where the Caribbean meets the Atlantic.

  • Junior Suite Pool View
  • Adults Only
  • All-Inclusive includes all meals, drinks, activities and more
  • FREE Wi-Fi
  • Honeymoon amenities available
7 nights with air from $2,535
 
 
Majestic Elegance Punta Cana Beach Resort, Golf, Casino & Spa

Majestic Elegance Punta Cana Beach Resort, Golf, Casino & Spa

This spectacular resort is surrounded by magnificent landscapes and offers guests extreme comfort and style.

  • Junior Suite
  • All-Inclusive includes all meals, drinks, activities and more
  • FREE Wi-Fi
7 nights with air from $2,545
 
 
Sanctuary Cap Cana - All Inclusive by Playa Hotels & Resorts

Sanctuary Cap Cana - All Inclusive by Playa Hotels & Resorts

This resort's architecture and interior design are highlighted by rich woods, marble and tile, from the lobby down to the sandy-white beach and on into the resort's 176 handsomely-appointed suite and villa accommodations.

  • Premium Luxury Junior Suite Ocean View
  • Adults Only
  • All-Inclusive includes all meals, drinks, activities and more
  • FREE shuttle to and from Punta Espada Golf Club
7 nights with air from $2,655
 
 

Aruba

Renaissance Aruba Resort & Casino

Renaissance Aruba Resort & Casino

This resort offers access to a private island featuring family-oriented Iguana Beach and the adults-only Flamingo Beach.

  • Island View
  • FREE Wi-Fi
  • FREE access to the private island
7 nights with air from $2,185
 
 
Aruba Marriott Resort & Stellaris Casino

Aruba Marriott Resort & Stellaris Casino

This lovely resort is a treasured jewel at the heart of Aruba's fashionable Palm Beach neighborhood.

  • Limited View
7 nights with air from $2,785
 
 
Riu Palace Antillas

Riu Palace Antillas

This adults-only hotel in beautiful Palm Beach offers an inviting atmosphere and endless activity options.

  • Junior Suite Ocean View
  • Adults Only
  • All-Inclusive includes all meals, drinks, activities and more
  • FREE Wi-Fi
7 nights with air from $2,985
 
 

Grand Cayman

Sunshine Suites Resort

Sunshine Suites Resort

This comfortable all-suite hotel is just moments from the famous Seven Mile Beach.

  • Studio
  • FREE continental breakfast daily
  • FREE Wi-Fi
  • Kids 17 and younger stay FREE
7 nights with air from $2,085
 
 
The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

This exclusive oceanfront resort delivers a grand level of relaxation and luxury. Situated on 144 acres stretching from the Caribbean Sea to the North Sound, the resort features 365 guestrooms and suites.

  • Garden View - King Bed
  • Kids 17 and younger stay FREE
7 nights with air from $4,539
 
 
Rates are based on roundtrip air travel to/from Newark (EWR) for Aruba and Grand Cayman and Boston (BOS) for Dominican Republic and are per person, based on double occupancy. Advertised vacation rate(s) valid for departures 1/26/19. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult.
Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]