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Chicago to Jamaica Deals

Chicago to Jamaica Deals

All-Inclusive Vacation Packages w/ Round-Trip Air

Chicago, book your all-inclusive Jamaica trip with Vacation Express today! These package deals include round-trip air for a getaway from Chicago to Jamaica, accommodations, hotel taxes and local representative. We offer affordable vacation packages and unbeatable deals on all-inclusive resorts, which include all meals, unlimited drinks and exciting entertainment at one great price.

Looking for more savings? Visit our Cyber Week Vacation Deals page to browse deals at over 100 hotels and resorts. Plus, find more ways to save when you visit our Coupon Codes page.

Deja Resort
  • Kids Stay, Play & Eat Free

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

Fall/Winter 2022 Deals

3 Nights From:

$838*: Now-12/15

Winter/Spring 2023 Deals

5 Nights From:

$966*: 3/1-4/30

 

$989*: 1/4-2/28

Holiday Inn Montego Bay
  • 67% Off
  • 1 Kid Stays, Plays & Eats Free

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

Fall/Winter 2022 Deals

3 Nights From:

$899*: Now-12/15

Winter/Spring 2023 Deals

5 Nights From:

$1047*: 3/1-4/30

 

$1159*: 1/4-2/28

Ocean Eden Bay
  • Up to 62% Off
  • Adults-Only Getaway

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

Fall/Winter 2022 Deals

3 Nights From:

$999*: Now-12/15

Winter/Spring 2023 Deals

5 Nights From:

$1225*: 3/1-4/30

 

$1369*: 1/4-2/28

Royalton Blue Waters Montego Bay Resort
  • Up to $600 Resort Credit††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

Fall/Winter 2022 Deals

3 Nights From:

$1499*: Now-12/15

Winter/Spring 2023 Deals

5 Nights From:

$1786*: 3/1-4/30

 

$1798*: 1/4-2/28

Trip Protection & Insurance

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. *$838 price is based on travel from Chicago [ORD] to Deja Resort for 3 nights on December 2. 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 from O'Hare International Airport, 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 12/2/22. 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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