Chicago Timeshares

Timeshares in Chicago allow travelers to enjoy one of America's most vibrant cities every year. Experience the art scene, nightlife, and more for an affordable price when you purchase one of our Chicago timeshare resales—up to 70% off the developer price!

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Timeshares in Chicago, Illinois

Chicago is full of wonderful contrasts, and you can explore them all with a Chicago timeshare. You'll experience the classic urban elements of a big city, like breathtaking skyscrapers, as well as surprising spots where nature thrives. You'll find the most fancy establishments, as well as the supremely casual. You'll encounter attractions that scream innovation, as well as relics of, and references to, a time gone by.

Encounter world-famous artworks like American Gothic and Cloud Gate, along with little known but promising talents, as you take in Chicago's diverse and exceptional art scene, or go skating at the McCormick Tribune Ice Rink. Sip an old-fashioned in 1920s-inspired Bordel. Feel your heart beat faster as you take in the city from the top of a skyscraper, or see an enormous, authentic dinosaur skeleton. Meander through indoor and outdoor gardens or stroll through the city's parks. If you're looking for new experiences, you'll find them in Chicago, and there's enough to explore that you'll experience something new for years to come—making a Chicago timeshare an ideal choice.

Save up to 70% on a timeshare in Chicago when you purchase on the secondary market. When you buy from a current owner, instead of a resort developer, you avoid price markups associated with sales commissions and promotional events, which do nothing to improve vacation quality. Plus, you can complete the entire research and purchase process from the comfort of your home, and feel secure in the fact that you're working with an established industry leader, when you buy a chicago timeshare resale from

Want to learn more about Chicago timeshare resales and the sublime vacation experiences they provide? Fill out the form to the right or give us a call at 1-877-815-4227.

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Possibilities with Timeshares in Chicago

Top Chicago Resorts

Chicago resorts come with incredible accommodations and amenities, and are made even better by their supreme locations—such as Printer's Row and the Magnificent Mile. Unit interiors are often as chic as the city itself, with some even inspired by famous designers like Frank Lloyd Wright. Chicago resorts sometimes offer amenities like in-room massages, onsite dining, valet parking, and more. You're sure to feel catered to when you use your timeshare in Chicago.

Things to Do in Chicago

Top 3 Amenities

Art, History, and More

Chicago hosts a rich array of museums. Art enthusiasts can head to the Art Institute of Chicago to see over 300,000 pieces, including American Gothic. Other art museums include Smart Museum of Art, the National Museum of Mexican Art, and more. There's also an extensive amount of science museums, including The Field Museum, where you'll find SUE, the world's largest and most well-preserved T-rex fossil. History buffs will be fascinated by the DuSable Museum of African american History and the Chicago History Museum.

Millenium Park

Millenium Park is a must-see attraction for travelers. The Park often hosts events and is full of concession stands, acclaimed art and architecture, and more. Notable features include Cloud Gate, a massive metal sculpture that looks like a giant bean with a reflective surface, The Boeing Galleries, The Jay Pritzker Pavilion, and the McCormick Tribune Ice Rink.

360 Chicago

360 Chicago, the observatory atop the John Hancock Center—a 100-story skyscraper—is the perfect spot for panoramic views of the city. If you're a Chicago timeshare owner, and you're not afraid of heights, you will enjoy this breathtaking vantage point and the photo opportunities it offers. For an especially intense experience, view the surrounding city from TILT, part of the observation deck where guests can lean on glass panels that give them more downward-facing views.

Chicago Shopping

Chicago offers a fabulous collection of shops to explore. With a timeshare in chicago, you can visit Dial M for Modern, to find a mix of 70s-era and modern Danish and American furniture—even if you're not looking to buy furniture, it's worth a visit. Gather Home and Lifestyle is a general store where all of the products are locally produced. Transistor is an art gallery, recording studio, and record shop all in one. Chicago offers a wide range of shops that often hit a unique balance of chic and quirky.

Bars and Taverns

You don't have to worry about boring nights with a Chicago timeshare. The city's bars are numerous and diverse. For cheap drinks and lots of entertainment, head to Slippery Slope, for beverages, a dance floor, skeeball, and more, or head to Headquarters Beercade for vintage arcade games, cheap cocktails, and craft beer. Bordel is a speakeasy with nightly live entertainment that includes jazz and burlesque. For a hip vibe and unique cocktails, visit the Violet Hour.

Nature in Chicago

While the city is an urban environment, there are still opportunities for you to enjoy nature. For a workout and scenic views of Lake Michigan, enjoy a jog, run, or bike ride on the 18-mile Chicago Lakefront Trail, which is part of famous Grant Park. To see beautiful and diverse plants, visit the lush gardens of Garfield Park Conservatory, which includes two acres inside—which you can enjoy even in winter—and 12 acres outside. In the summer, also visit the Lurie Garden.

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