Enjoy a 7 nights of Caribbean Resort Waterfront Villa-Style Accommodations. The Verandah Resort & Spa is an eco-friendly Caribbean beachfront resort with two spectacular white-sand beaches; four pools; nature trails to historic Devil's Bridge; four restaurants; tennis & fitness center; non-motorized water sports; kids club; mini golf; mini cinema; and the world class Tranquility Body & Soul Spa. Perfect for those seeking a romantic hideaway; family vacation or just looking to escape and leave the world behind... 7 Nights of luxurious accommodations, for up to two rooms double occupancy. Winner responsible for airfare and all inclusive supplement of 140+tax per person per night. (Additional peak season surcharge of $100 per person, per night applies Dec21-April 15)

Experience a private 100 acre pennisula on Antigua's southeastern coast where clear turquoise waters surround your own private oasis. Two magnificent white-sand beaches; six pools; four distrinct restaurants; non-motorized water sports; tennis & fitness center; supervised kids activities; spa and nightly entertainment. St James's Club will leave you with amazing island memories to last a lifetime. 7 Nights of luxurious accommodations, for up to two rooms double occupancy. Winner responsible for airfare and all inclusive supplement of 140+tax per person per night. (Additional peak season surcharge of $100 per person, per night applies Dec21-April 15)

Enjoy an exclusive, 135 acre private-island hideaway near the southern tip of St Vincent & the Grenadines. Offers 5 dazzling white sand beaches, dining, water sports, nature trails, tennis fitness center, swimming pool with waterfall and spa treatments. 7 Nights of luxurious accommodations, for up to two rooms double occupancy. Winner responsible for airfare and all inclusive supplement of 140+tax per person per night. (Additional peak season surcharge of $100 per person, per night applies Dec21-April 15)

Visit Marriott Lincolnshire Resort to experience theatre, includes guest room, 1 King or 2 Double, Dinner for 2, 2 Theater Tickets for 2 Adults & Breakfast for 2 Adults chicagomarriottlincolnshire.com Exp: 10/1/2018

Enjoy some Deep Eddy's Grapefruit Vodka on the Beach with your new beach blanket by Palm Beach Crew. Family size water proof blanket with weighted corners Machine Washable/Air Dry Weighted & removable corner pockets. Includes 4 designer sandbags. Water proof easy access pocket for your valuables. Folds into itself for easy transport or place it inside it's wetbag.