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Chicago Caribbean Vacation Deals

Chicago to the Caribbean Deals

Vacation Deals to Amazing Resorts

Chicago, your next Caribbean getaway is closer than you think when you book a Vacation Express package, accommodations, local representative and round-trip air from Chicago to the Caribbean! All-inclusive resorts take care of all meals, unlimited drinks and nightly entertainment. All you have to do is book!

Antigua

Royalton Antigua Resort & Spa
  • Up to 72% Off
  • 1 Kid Stays & Eats Free in Select Rooms
  • Up to $600 Resort Credit††

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$139*: 4/1-4/30

 

$149*: 1/3-3/31

Aruba

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$264*: 1/3-3/31

 

$299*: 4/1-4/30

Barbados

EUROPEAN PLAN RESORT STAYS

Per Night From:

$99*: 4/1-4/30

 

$168*: 1/3-3/31

Curacao

EUROPEAN PLAN RESORT STAYS

Per Night From:

$89*: 4/1-4/30

 

$129*: 1/3-3/31

Grenada

Royalton Grenada Resort & Spa
  • 60% Off
  • $300 Resort Credit††

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$199*: 4/1-4/30

 

$229*: 1/3-3/31

Saint Lucia

Starfish St Lucia
  • Up to 80% Off
  • $300 Resort Credit††
  • First Kid Stays, Plays & Eats Free

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$113*: 3/1-4/30

 

$123*: 1/3-3/31

St. Maarten

Sonesta Maho Beach Resort, Casino & Spa
  • 45% Off
  • Up to $120 Resort Credit††

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$147*: 4/1-4/30

 

$169*: 1/3-3/31

St. Thomas

Bolongo Bay Beach Resort
  • Early Booking Sale
  • Added Amenities!

EUROPEAN PLAN RESORT STAYS

Per Night From:

$189*: 4/1-4/30

 

$199*: 1/3-3/31

Turks & Caicos

The Alexandra
  • Up to 60% Off

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$349*: 4/1-4/30

 

$387*: 1/3-3/31

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. *Prices reflect hotels that feature Breakfast Plans, European Plans, Continental Plans, Inclusive Plans and All-Inclusive Plans. 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. Hotel-only prices include hotel and hotel taxes and are per person per night, based on double occupancy for minimum 3-night stays. Above offers are only valid for new bookings and are not valid for groups. Air can be added for an additional charge to hotel-only offers. 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 are limited and subject to change without prior notice. Hotels in Saint Lucia charge a Country Sustainability Fee of $4 USD per person, per night. Fees are subject to change without notice and are payable at the hotel. Book by 1/20/21. 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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