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Vacations Packages with Marriott from Chicago

Escape the Windy City for a Vacation

With nearly 50 million visitors annually and a host of must-see landmarks, Chicago is without a doubt a popular destination for tourists. That rush of visitors flocking to popular attractions including Millennium Park and Navy Pier may have Windy City residents dreaming of a vacation destination far away. Vacations by Marriott has just the right getaway package to make that temptation a reality for you. Spend some time beachfront in Cancun, snorkel in St. Thomas or say “aloha” to Kahului, HI.

Our vacation packages from Chicago are sure to blow you away. And remember, Vacations by Marriott is the only place you can book a complete vacation with airfare and earn Marriott Rewards® or SPG ® points! 

Featured Hotels



Frenchman's Reef & Morning Star Marriott Beach Resort


St. Thomas, Virgin Islands (US)

Frenchman’s Reef & Morning Star Beach Resort welcomes guests to the ultimate US Virgin Island hotel experience. The Reef Tower features fresh Caribbean décor and state-of-the-art amenities. Our infinity pools feature stunning St. Thomas views, while a kids splash zone provides plenty of space for family time. Guests can enjoy the pristine beachfront at the Morning Star Beach Club and Sea Cliff Tower, or relax at the luxury Lazule Sea Spa & fitness center.  

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Marriott Cancun Resort


Cancun, Mexico

Beachside luxury awaits you here in Mexico. Boasting modern amenities and just steps from sparkling seas, CasaMagna Marriott Cancun Resort elevates hotel living to a new level. Whether you're here for a romantic getaway or a fun family vacation, our hotel offers the very best in elegance and convenience for your Cancun visit. Pamper yourself with jaw-dropping views of the Caribbean, Nichupte Lagoon, and our manicured hotel grounds.

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Courtyard Maui Kahului Airport


Kahului, HI

Sit back and relax on the shores of paradise right off the runway when you stay at Courtyard Maui Kahului Airport. With Upcountry Maui, Paia and the many pristine beaches of the island close by, you’ll spend less time commuting and more time enjoying a productive business trip or vacation. Soak up the sun in style at our sparkling outdoor pool or relax under one of our cabanas. After a long day, wind down in our spacious guest rooms, complete with modern decor and luxury bedding.

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The Ritz-Carlton, St. Thomas


St. Thomas, Virgin Islands (US)

Experience a new era of refinement at the newly redesigned Ritz-Carlton, St. Thomas. The beloved resort welcomes families, couples, and adventure-seekers to encounter the beauty of the Caribbean in a new light. Be captivated by peerless Turquoise Bay and green mountain views, endless beaches, thrilling water sports, and a stunning destination for celebrations large and small at The Ritz-Carlton, St. Thomas.

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JW Marriott Cancun Resort & Spa


Cancun, Mexico

Get ready to treat yourself to the very best here in Mexico. Located in the heart of the Hotel Zone, the landmark JW Marriott Cancun Resort & Spa offers an extraordinary hotel experience. Our 448 elegant rooms and suites feature private balconies with stunning views of Cancun's white sand beaches and the turquoise waters of the Caribbean as well as marble bathrooms, pillowtop mattresses, and 24-hour room service.

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Waikiki Beach Marriott Resort & Spa


Honolulu, HI

Discover a true resort hotel with unrivaled service, luxurious amenities and sweeping views of the Pacific Ocean at Waikiki Beach Marriott Resort & Spa. Explore an array of area attractions, including Pearl Harbor and Waikiki Aquarium. Play in the surf or relax with a poolside drink at the Moana Terrace. Take in soothing ocean breezes from the private lanai of your hotel room or suite, complete with island-style décor and plush bedding.  

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Marriott Puerto Vallarta Resort & Spa


Puerto Vallarta, Mexico

Nestled between the Sierra Madre Mountains and beautiful Banderas Bay, CasaMagna Marriott Puerto Vallarta Resort & Spa is the ultimate retreat for discerning travelers. Ranked as one of the top 10 Pacific Riviera hotels by Condé Nast Traveler, CasaMagna Marriott offers deluxe accommodations, high-tech amenities and easy access to golf courses, shopping and nightlife. A pristine stretch of sandy golden beach is just steps from our resort.

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Waikoloa Beach Marriott Resort & Spa


Waikoloa, HI

Our newly redesigned hotel offers spacious, modern accommodations with patios and lanais overlooking beautiful Anaeho'omalu Bay. The transformed Na Hale wing offers an intimate residential experience and some of the most coveted guestrooms and suites across the resort. Step out onto our pristine, sandy beach - the only one of its kind in our resort area. Play in our three outdoor pools and waterslide, and golf on two 18-hole championship courses.

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