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Chicago Travelzoo Deals

Chicago to Jamaica Vacation Package Deals

Jamaica All-Inclusive Vacation Packages w/ Air

$749* price includes 4-night Superior Partial Ocean View accommodations, meals, drinks, round-trip flights & taxes.
▪ Save up to $233 off per person at Holiday Inn Resort Montego Bay + Kids 12 & Under Stay & Eat Free††!
▪ Amazing deals also available at Grand Palladium Lady Hamilton & Excellence Oyster Bay [See below for details]

Book By: 12/21/19 ▪ Travel: 12/10/19 - 8/14/19

Holiday Inn Montego Bay
  • All-Inclusive, Family Deal - Oceanfront Resort
  • Up to 2 Kids 12 & Under Stay & Eat Free
  • 2 Pools, Swim-Up Bar & Oceanfront Jacuzzi
  • Free Upgrade to Superior Partial Ocean View Room


4 Nights From:

$749*: Jan 12, 19, 26


$779*: Select Dates, Apr 1 - May 31


$784*: Select Dates, Jan 2 - 31


$799*: Select Dates, Feb 1 - Mar 31

Grand Palladium Lady Hamilton Resort and Spa
  • Free Upgrade to One Bedroom Suite w/Free Wi-Fi
  • Jamaica's Largest Pool & Swim-up Bar & Spa
  • All-Inclusive, Beachfront Resort w/Pool & Beach Service
  • Up to 45% Off + $1500 in Resort Credits††
Excellence Oyster Bay
  • Luxury, All-Inclusive, Adults-Only Resort on a Private Peninsula
  • 8 A la Carte Dining Options, 10 Bars/Lounges + 24-Hour Room Service
  • 3 Swimming Pools & 4 jacuzzis with Waiter Service
  • Non-motorized water sports (sailing, sea kayaking, paddle board, snorkeling)

Traveling within three days? Our Travel Advisors can make it happen! Call 1-800-309-4717 to book.
Kid's offer based on one child per full paying guest and offered on select departures only; qualifying ages and maximum number of kids vary by resort and applies to hotel cost only. Airfare, transfers & booking fees not included. ††Restrictions apply. Call for details. $1500 in resort credits can be used toward spa treatments, room upgrades based on availability, romantic dinners, bottles of wine and more. *Advertised prices available for bookings made electronically through your travel agent or on vacationexpress.com; small service fee of $10 applies when booking through Vacation Express Call Center. Prices are per person, based on double occupancy. For full terms and conditions, hotel and description of all services, please refer to the Vacation Express 2020 Brochure or call for details. Vacation Express now accepts debit cards that offer the same consumer protection as credit cards. Some upgrades are subject to availability upon check-in. Packages at the above prices are based on travel, are limited and subject to change without prior notice and are on coach air with Spirit Airlines, American Airlines or other U.S. certified carriers or Vacation Express public charter flights operated by Allegiant Air, Miami Air International, Swift Air, LLC., Sunwing Airlines, VivaAerobus or Volaris. Airfares are per person, reflect lowest available airfare at time of printing, are subject to change and are based upon availability of class of service. Baggage charges and allowances vary by carrier and can change frequently. Most major carriers are charging a fee for checked baggage. Some airlines, including Spirit Airlines, are charging a fee for all checked and carry-on baggage. Clients must check their respective airline for the most current baggage information. Book by 12/21/19. Not responsible for errors or omissions. Registered Florida Seller of Travel no. St 38441. State of California Seller of Travel Certificate of Registration #2107538-40.

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