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Travelzoo Deals

Chicago [ORD] to Jamaica Vacation Package Deals

Samsara Cliff Resort All-Inclusive Vacation Packages w/Round-Trip Air

$549* price includes 3-night Garden View Room accommodations, round-trip flights & taxes.
▪ Save up to $105 per person at Samsara Cliff Resort + Up to Two Kids Stay & Eat Free!
▪ Great deals also available at Ocean Coral Spring and Royalton Negril [See below for details]

Book By: 6/30/23 ▪ Travel: 6/10/23 – 12/20/23


Samsara Cliff Resort
  • Boutique Oceanfront Resort w/Beautiful Seaviews
  • All-Inclusive from 10am to 10pm + Up to 2 Kids Free!
  • Cliff Jumping, Golf Nearby, Nightly Entertainment
  • Stay at 1, Play at 2 Resorts w/Comp. Shuttle Daily

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$549*: Aug 23, Sep 6

 

$559*: Select Dates, Sep 1 - Oct 31

 

$564*: Select Dates, Jun 12 - Aug 31

 

$634*: Select Dates, Nov 1 - Dec 20

Ocean Coral Spring
  • All-Inclusive, Beachfront Resort
  • 9 Restaurants, Disco Bar + Mike's Coffee
  • Entertainment Theatre + Bowling Alley
  • Pool, Kid's Water Playground & Lazy River

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$785*: Sep 1 - Nov 31

 

$842*: Jun 12 - Aug 31

Royalton Negril, An Autograph Collection All-Inclusive Resort
  • All Inclusive Luxe Resort w/Stunning Beach
  • $300 in Resort Credits on Spa Serv. Upgrades & More††
  • Luxe Jr Suite Oceanview w/24 Hr. Rm. Service
  • Splash Park, Kids/Teens Clubs + Day & Night Entertainment

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

3 Nights From:

$859*: Sep 1 - Nov 31

 

$899*: Jul 1 - Aug 31

Traveling within three days? Our Travel Advisors can make it happen! Call 1-800-309-4717 to book.
Kid's hotel 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 does not apply to airfare, transfers & booking fees. ††Restrictions apply. Call for details. *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 information and description of all services, please refer to vacationexpress.com or call for details. Some upgrades are subject to availability upon check-in. Packages above are limited and subject to change without prior notice and are based on travel on coach/economy air with Spirit Airlines, American Airlines or other U.S. certified carriers. 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 6/30/23. 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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