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We can GET YOU the best deals from Chicago to Caribbean!
No reservation system can provide all the deals from Chicago
to Caribbean in one place.
We are professional travel advisors, we've been to Caribbean,
we've checked out the hotels, we know the best beach areas, and will
provide you the best Caribbean deals!
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1 to 35 from 297 |
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| Origin | Destination | Price | Nights | Hotel/Rating | Days/Dates | Description and Inclusions |
| Chicago | Punta Cana packages deals | $429 | 3 | Occidental Grand Punta Cana - 3.5 | Daily - 11/30/09-12/14/09 | All Inclusive includes, all meals, drinks, activities and more! - Check_Availability_3 |
| Chicago | Bermuda packages deals | $474 | 3 | Grotto Bay Beach Resort - 3.5 | Daily - 12/1/09-12/13/09 | European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Ocean View. Includes Kids 16 & younger stay FREE. - Check_Availability_3 |
| Chicago | San Juan packages deals | $525 | 3 | Wyndham Rio Mar Beach Resort and Spa - 4 | Daily - 11/30/09-12/11/09 | European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes reduced rate, daily breakfast buffet PLUS Kids 18 & younger stay FREE. - Check_Availability_3 |
| Chicago | San Juan packages deals | $553 | 3 | The Ritz-Carlton,San Juan Hotel, Spa & Casino - 5 | Daily - 11/30/09-12/11/09 | European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes Kids 17 & younger stay FREE. - Check_Availability_3 |
| Chicago | San Jose packages deals | $557 | 4 | Barcelo San Jose Palacio - 3 | Daily - 11/30/09-12/13/09 | European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes Kids 12 & younger stay FREE. - Check_Availability_3 |
| Chicago | St. Maarten packages deals | $574 | 3 | Grand Case Beach Club - 3 | Daily - 11/30/09-12/13/09 | European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes welcome bottle of wine, daily Continental breakfast for ALL, non-motorized water sports and more! - Check_Availability_3 |
| Chicago | Montego Bay packages deals | $583 | 3 | Sunset Beach Resort and Spa - 3 | Daily - 11/30/09-12/14/09 | All Inclusive includes, all meals, drinks, activities and more! PLUS two Kids 15 & younger stay FREE. - Check_Availability_3 |
| Chicago | Montego Bay packages deals | $583 | 3 | Sunset Beach Resort and Spa - 3 | Daily - 11/30/09-12/14/09 | All Inclusive includes, all meals, drinks, activities and more! PLUS two Kids 15 & younger stay FREE. - Check_Availability_3 |
| Chicago | Montego Bay packages deals | $583 | 3 | Sunset Beach Resort and Spa - 3 | Daily - 11/30/09-12/14/09 | All Inclusive includes, all meals, drinks, activities and more! PLUS two Kids 15 & younger stay FREE. - Check_Availability_3 |
| Chicago | Negril packages deals | $584 | 3 | Riu Negril - 4 | Daily - 11/30/09-12/14/09 | All Inclusive includes, all meals, drinks, activities and more! PLUS reduced rate. - Check_Availability_3 |
| Chicago | Negril packages deals | $584 | 3 | Riu Negril - 4 | Daily - 11/30/09-12/14/09 | All Inclusive includes, all meals, drinks, activities and more! PLUS reduced rate. - Check_Availability_3 |
| Chicago | Negril packages deals | $584 | 3 | Riu Negril - 4 | Daily - 11/30/09-12/14/09 | All Inclusive includes, all meals, drinks, activities and more! PLUS reduced rate. - Check_Availability_3 |
| Chicago | Montego Bay vacation package deal | $588 | 3 | 4 Star hotel guaranteed upon arrival - 4 | Thu - 1/7-1/28 | All Inclusive - Includes all meals, beverages, entertainment, activities, hotel taxes, round trip airport shuttle, tips and more! - You pick the dates and price, we provide the hotel and you save! Our special program guarantees star rating or better. - Check_Availability_2 |
| Chicago | Montego Bay vacation package deal | $588 | 3 | 4 Star hotel guaranteed upon arrival - 4 | Thu - 1/7-1/28 | All Inclusive - Includes all meals, beverages, entertainment, activities, hotel taxes, round trip airport shuttle, tips and more! - You pick the dates and price, we provide the hotel and you save! Our special program guarantees star rating or better. - Check_Availability_2 |
| Chicago | Montego Bay vacation package deal | $588 | 3 | 4 Star hotel guaranteed upon arrival - 4 | Thu - 1/7-1/28 | All Inclusive - Includes all meals, beverages, entertainment, activities, hotel taxes, round trip airport shuttle, tips and more! - You pick the dates and price, we provide the hotel and you save! Our special program guarantees star rating or better. - Check_Availability_2 |
| Chicago | Ocho Rios vacation package deal | $588 | 3 | Shaw Park Beach Hotel & Spa - 3.5 | Thu - 1/7-1/28 | All Inclusive - Includes all meals, beverages, entertainment, activities, hotel taxes, round trip airport shuttle, tips and more! - - Check_Availability_2 |
| Chicago | Ocho Rios vacation package deal | $588 | 3 | Shaw Park Beach Hotel & Spa - 3.5 | Thu - 1/7-1/28 | All Inclusive - Includes all meals, beverages, entertainment, activities, hotel taxes, round trip airport shuttle, tips and more! - - Check_Availability_2 |
| Chicago | Ocho Rios vacation package deal | $588 | 3 | Shaw Park Beach Hotel & Spa - 3.5 | Thu - 1/7-1/28 | All Inclusive - Includes all meals, beverages, entertainment, activities, hotel taxes, round trip airport shuttle, tips and more! - - Check_Availability_2 |
| Chicago | Nassau packages deals | $595 | 3 | Sheraton Nassau Beach Resort - 4 | Daily - 11/30/09-12/15/09 | European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes daily breakfast PLUS Kids 17 & younger stay FREE. - Check_Availability_3 |
| Chicago | Barbados packages deals | $603 | 3 | Accra Beach Hotel & Resort - 3.5 | Daily - 11/30/09-12/12/09 | European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes Kids 11 & younger stay FREE - Check_Availability_3 |
| Chicago | Montego Bay packages deals | $609 | 4 | The Ritz-Carlton Golf and Spa Resort, Rose Hall - 5 | Daily - 11/30/09-12/13/09 | European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes 4th night FREE PLUS Kids 17 & younger stay FREE. (Must be booked by 12/15/09) - Check_Availability_3 |
| Chicago | Montego Bay packages deals | $609 | 4 | The Ritz-Carlton Golf and Spa Resort, Rose Hall - 5 | Daily - 11/30/09-12/13/09 | European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes 4th night FREE PLUS Kids 17 & younger stay FREE. (Must be booked by 12/15/09) - Check_Availability_3 |
| Chicago | Montego Bay packages deals | $609 | 4 | The Ritz-Carlton Golf and Spa Resort, Rose Hall - 5 | Daily - 11/30/09-12/13/09 | European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes 4th night FREE PLUS Kids 17 & younger stay FREE. (Must be booked by 12/15/09) - Check_Availability_3 |
| Chicago | Nassau packages deals | $611 | 3 | Riu Palace Paradise Island - 4.5 | Daily - 11/30/09-12/15/09 | Ocean View Junior Suite. All Inclusive includes, all meals, drinks, activities and more! - Check_Availability_3 |
| Chicago | Aruba packages deals | $614 | 3 | Amsterdam Manor Beach Resort Aruba - 3.5 | Daily - 11/30/09-12/14/09 | European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes reduced rate. - Check_Availability_3 |
| Chicago | Aruba packages deals | $616 | 3 | Renaissance Aruba Resort and Casino - 4.5 | Daily - 11/30/09-12/14/09 | European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes reduced rate. - Check_Availability_3 |
| Chicago | St. Thomas packages deals | $623 | 4 | Wyndham Sugar Bay Resort and Spa - 4 | Daily - 12/1/09-12/11/09 | European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes 3rd & 4th night FREE, $100 food and beverage credit PLUS Kids 17 & younger stay FREE. (Must be booked by 11/30/09) - Check_Availability_3 |
| Chicago | Montego Bay vacation package deal | $637 | 3 | 4 Star hotel guaranteed upon arrival - 4 | Thu - 1/7-1/28 | All Inclusive - Includes all meals, beverages, entertainment, activities, hotel taxes, round trip airport shuttle, tips and more! - You pick the dates and price, we provide the hotel and you save! Our special program guarantees star rating or better. - Check_Availability_2 |
| Chicago | Montego Bay vacation package deal | $637 | 3 | 4 Star hotel guaranteed upon arrival - 4 | Thu - 1/7-1/28 | All Inclusive - Includes all meals, beverages, entertainment, activities, hotel taxes, round trip airport shuttle, tips and more! - You pick the dates and price, we provide the hotel and you save! Our special program guarantees star rating or better. - Check_Availability_2 |
| Chicago | Montego Bay vacation package deal | $637 | 3 | 4 Star hotel guaranteed upon arrival - 4 | Thu - 1/7-1/28 | All Inclusive - Includes all meals, beverages, entertainment, activities, hotel taxes, round trip airport shuttle, tips and more! - You pick the dates and price, we provide the hotel and you save! Our special program guarantees star rating or better. - Check_Availability_2 |
| Chicago | Punta Cana vacation package deal | $637 | 3 | Sirenis Resort Punta Cana Casino & Spa - 4 | Wed - 1/6-1/20 | All Inclusive - Includes all meals, beverages, entertainment, activities, hotel taxes, round trip airport shuttle, tips and more! - - Check_Availability_2 |
| Chicago | Punta Cana packages deals | $640 | 3 | Melia Caribe Tropical Resort - 4 | Daily - 11/30/09-12/14/09 | Junior Suite. All Inclusive includes, all meals, drinks, activities and more! - Check_Availability_3 |
| Chicago | Ocho Rios vacation package deal | $647 | 3 | Sunset Jamaica Grande Resort & Spa - 4 | Thu - 1/7-2/4 | All Inclusive - Includes all meals, beverages, entertainment, activities, hotel taxes, round trip airport shuttle, tips and more! - - Check_Availability_2 |
| Chicago | Ocho Rios vacation package deal | $647 | 3 | Sunset Jamaica Grande Resort & Spa - 4 | Thu - 1/7-2/4 | All Inclusive - Includes all meals, beverages, entertainment, activities, hotel taxes, round trip airport shuttle, tips and more! - - Check_Availability_2 |
| Chicago | Ocho Rios vacation package deal | $647 | 3 | Sunset Jamaica Grande Resort & Spa - 4 | Thu - 1/7-2/4 | All Inclusive - Includes all meals, beverages, entertainment, activities, hotel taxes, round trip airport shuttle, tips and more! - - Check_Availability_2 |
International airport taxes NOT included. Prices are per person, based on double occupancy and include: Air Only=round trip airfare; Hotel only=accommodations; European plan=accommodations plus round trip airfare and ground transportation, if all inclusive add meals, beverages, activities and tips. Services vary at each hotel, please view hotel description or call our reservation center for details. International airport taxes not included. These rates are subject to availability. Our price guarantee: If any tour operator or vacation company has a lower price, we will match it and offer you a discount!
Caribbean deals from US:
