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Caribbean Vacation Packages from $565

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$200 Instant Air Credit
Valid from select Midwest gateways*
Book by 3/31/15 for travel anytime
Pleasant Caribbean Holidays
Jamaica

4 nights from $705

Bahamas

3 nights from $835

Dominican Republic

3 nights from $579

More Great Deals






Puerto Rico

3 nights from $565

St. Lucia

3 nights from $895

Turks & Caicos

3 nights from $1,135

Aruba

3 nights from $685

USVI

3 nights from $639

Bermuda

3 nights from $759

St. Martin

3 nights from $935

Barbados

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Grenada

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Rates are based on roundtrip air travel to/from Kansas City (MCI) departures to Aruba, Miami (MIA) departures to Bahamas and Puerto Rico, Chicago (ORD) departures to Bermuda, Dominican Republic and Jamaica, Boston (BOS) departures to St. Lucia, Turks & Caicos and US Virgin Islands and New York (JFK) departures to St. Martin, for select travel 4/27/15 for Bermuda, 4/23/15 for Puerto Rico, 5/3/15 for Jamaica and 5/4/15 for all other destinations. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Rates do not include a $10 per person Tourist Card fee payable upon arrival in the Dominican Republic.

$200 Instant Air Credit Offer: Valid on new bookings made 9/15/14 - 3/31/15 for travel any time to Mexico, the Caribbean or Central America. Minimum 3-night hotel accommodations and roundtrip airfare required. Discount is per booking and taken at the time of booking. *Travel must originate from one of the following departure gateways only: Indianapolis (IND), Kansas City (MCI), Chicago (ORD), Des Moines (DSM), Detroit (DTW), Flint (FNT), Grand Rapids (GRR), Kalamazoo/Battle Creek (AZO), Lansing (LAN), Saginaw (MBS), Traverse City (TVC), Duluth (DLH), Minneapolis (MSP), Rochester (RST), Appleton (ATW), Eau Claire (EAU), Green Bay (GRB), La Crosse (LSE), Madison (MSN), Milwaukee (MKE), Wausau (CWA), Bismarck (BIS), Fargo (FAR), Grand Forks (GFK), Minot (MOT), Rapid City (RAP), Sioux Falls (FSD), Lincoln (LNK), Omaha (OMA), Cincinnati (CVG), Cleveland (CLE), Columbus (CMH) and Pittsburgh (PIT). Offer is subject to change or cancellation at any time at the sole discretion of Pleasant Holidays. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]



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