Vacation Packages w/ Airfare, Hotel & Tours to Puerto Rico from ORD - Chicago

Thinking about traveling to Puerto Rico from Chicago? Puerto Rico is a vibrant Caribbean destination known for its beautiful beaches, rich history, and lively culture. From the colorful streets of Old San Juan to the lush rainforests of El Yunque National Forest, there is no shortage of things to se... read more

Beach Getaway at Hyatt Regency Grand Reserve Puerto Rico

At the Hyatt Regency Grand Reserve Puerto Rico, you'll be able to enjoy a luxurious beach vacation just steps away from the pristine ocean. Revel in upscale amenities in a secluded location on Coco Beach close to the expansive El Yunque National Forest, providing easy access for amazing activities both on and off the resort. Relax in the stunning lagoon-style pool, indulge in delicious Caribbean cuisine, and soak up year-round sunshine on this splendid beach vacation in Puerto Rico.

From
ORD $1,229 * Per Person

3+ Nights

2 People

* Vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air, airport taxes, transfers, and hotel. Additional baggage charges may apply. Rates are available for 1 to 9 travelers.

Puerto Rican Paradise

Are you craving a Caribbean vacation without the hassle of a passport? The Caribe Hilton is the answer you've been waiting for! Escape for 3, 4, 5, or 6 nights in San Juan, Puerto Rico, on the spectacular grounds of this historic resort. Spend your days relaxing at the spa, lounging under a cascading waterfall, and soaking up the pristine beach. Whatever paradise is for you, it's waiting at the Caribe Hilton.

From
ORD $670 * Per Person

3+ Nights

2 People

* Vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air, airport taxes, and hotel. Additional baggage charges may apply. Rates are available for 1 to 9 travelers.

Beachfront Oasis at Fairmont El San Juan Puerto Rico

Experience true bliss when you travel to Puerto Rico and stay in the phenomenal Fairmont El San Juan Hotel. You'll be staying right on the two-mile long Isla Verde Beach, surrounded by tall palm trees and lush greenery. Dive into any of the hotel's dazzling swimming pools, lay back with poolside service, and enjoy lively entertainment at the hotel's renowned nightclub.

From
ORD $1,221 * Per Person

3+ Nights

2 People

* Vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air, airport taxes, transfers, hotel and breakfast daily. Additional baggage charges may apply. Rates are available for 1 to 9 travelers.

Old San Juan, Puerto Rico – Adults Only Boutique Hotel Stay

Uncover the beauty and history of San Juan, Puerto Rico's vibrant capital, during this 3-6-night getaway. Enjoy a stay at the adults-only Palacio-Provincal, located in the heart of Old San Juan, putting you at the perfect place to see the highlights of the city, from stunning beaches to iconic attractions.

From
ORD $604 * Per Person

3+ Nights

2 People

The Town of Beautiful Sunsets: Rincón, Puerto Rico

Melt away stress with an exciting vacation in Rincón, Puerto Rico, known as the "Town of Beautiful Sunsets." Enjoy time at a gorgeous seaside hotel with easy access to Rincón's incredible beaches to surf, snorkel, scuba dive, or simply soak in the sun. Perfect for anyone who loves sunsets and calm ocean breezes, this Puerto Rico vacation has everything you need!