Chicago Timeshare: Vacation in the Windy City

TSO Chicago blog

If you’re searching for a metropolitan vacation, look no further than the Windy City. Chicago is one of the biggest cities in the U.S., full of things to do and see. From world-class museums and scenic river cruises to a growing food scene, there is never a dull moment in Chicago. Owning or renting a Chicago timeshare is the best way to ensure that you’ll see all that the city has to offer!

About Chicago Timeshare

Downtown Chicago

On the shores of Lake Michigan sits Chicago, the third most populous city in America. The land that later became Chicago was inhabited by native tribes in the mid-18th century and then settlers arrived in the area in the late 1700s. After the Northwest Indian War, the area was turned over to the US military. The Town of Chicago was officially organized in 1833 with just about 200 residents. In just seven years, the population grew to over 6,000. The City of Chicago was formed in 1837 and was the fastest-growing city in the world for decades. Sadly, in 1871, the Great Chicago Fire destroyed most of the city. During the rebuilding process, Chicago built the world’s first skyscraper. Rebuilding the city caused a boom in architecture and population, becoming the beautiful and popular city it is today.

Chicago is often considered one of the best cities to visit in the U.S. With beautiful architecture, world-class dining, impressive museums, and seemingly endless attractions, it’s no surprise that people love visiting Chicago. When buying or renting a timeshare in Chicago, you are guaranteed to be surrounded by things to see and do!

Things To Do Near Chicago Timeshare Resorts

Chicago has so much to offer its millions of yearly visitors. Whether you want to embrace the tourist lifestyle or you want to eat like a local, you can do it all in this incredible city! Every season has something to offer, from music festivals in the summer to a sprawling holiday market in the winter. There is so much fun waiting for you in Chicago and a timeshare is a perfect way to make sure you experience it all!

Attractions and Sightseeing

Skydeck Willis Tower

Chicago is one of the most beautiful cities in the world, so you’ll want to spend a few days of your visit to your timeshare exploring. In addition to walking around to see the city, there are a bunch of unique ways to experience Chicago. One of the most popular ways to tour the city is to take a riverboat cruise on the Chicago River, which runs through the city. For a birds-eye view of Chicago’s skyline, head to Willis Tower’s Skydeck Chicago. For a more adventurous perspective, step out onto The Ledge, an all-glass viewing box. Of course, the iconic Cloud Gate A.K.A. “The Bean” is a great way to take a selfie with Chicago’s cityscape.

There are many attractions throughout the city that are perfect for the whole family. A fun way to experience the city is to go to Maggie Daley Park and skate or scooter around the ribbon loop. The Lincoln Park Zoo is just minutes from downtown Chicago and is always free of charge. The 35-acre zoo is home to hundreds of species of animals and beautifully manicured park grounds, Shedd Aquarium, one of the world’s largest indoor aquariums, is another popular attraction and sits on the edge of Lake Michigan. A day at this aquarium is spent learning about and observing some amazing aquatic creatures, including penguins and beluga whales. Another beautiful site is Garfield Conservatory, a conservatory with 4.5-acres of indoor and outdoor gardens.


Wrigley Field

Chicago is home to many professional sports teams and, as a result, some pretty passionate sports fans. If you’re looking to catch a baseball game, Chicago is the place for you as they have two MLB teams. The Chicago Cubs play at Wrigley Field, an iconic Chicago landmark that was built in 1914 in the North Side. The other baseball team in Chicago, the White Sox, plays on the South Side where you can enjoy restaurants and bars before or after a game. If you’re visiting during football season, be sure to catch a Bears game at Soldier Stadium, which is also home to the Chicago Fire soccer team. The Blackhawks hockey team plays at the United Center, which is the country’s largest arena. The Chicago Bulls basketball team, which also plays at the United Center, is one of the most recognizable sports teams in the world.

Food, Arts, and Music

Chicago Arts

An important factor of any vacation is finding good food and a trip to your Chicago timeshare will not disappoint on that front. Of course, we can’t talk about food in Chicago without mentioning their world-famous deep-dish pizza. Some Chicago residents will argue about who makes the best deep-dish, but a cult classic choice is Lou Malnati’s. When you’re walking around the city, you’ll find a ton of options for a Chicago Italian beef sandwich but everyone will tell you to try one at Al’s. There are many guided food tours around Chicago, so if you want to taste your way around the city then you’re in luck!

Chicago is home to an ever-growing arts scene. There are museums and galleries all over the city, but art lovers must check out The Art Institute of Chicago. Within their world-renowned collection, you’ll see works from some of the world’s most acclaimed artists including Vincent van Gogh and Pablo Picasso. There is an abundance of live entertainment in Chicago including music festivals and a thriving theater district. A fun bit of live entertainment in Chicago is the famous Second City comedy club, where some of the biggest names in comedy, like Billy Murray and Amy Pohler, got their start. Another great museum for the whole family is the Field Museum of Natural History, which is home to the world’s most complete T-Rex ever found.

Best Chicago Timeshare Resorts

Some of the top timeshare brands in the industry have resorts in Chicago. Bluegreen Vacations as well as Hilton Grand Vacations Club are two of the most popular timeshare developers that can be found in the Windy City. For more information about these amazing Chicago timeshare resorts, keep reading!

Hotel Blake Chicago, A Bluegreen Resort

Hotel Blake is a Bluegreen timeshare resort in the Printer’s Row district of Chicago. This resort’s location is perfect for exploring the city! It’s within walking distance of many of Chicago’s best attractions, including Millenium Park and The Art Institute of Chicago. If you’re wanting to try some deep-dish pizza, Lou Malnati’s is just a five-minute walk from Hotel Blake. After an exciting day in the city, retreat to your spacious and modern suite. Hotel Blake doesn’t offer large multi-bedroom timeshare villas, but with all there is to do in Chicago, you might not spend much time in the room! If you need some extra room to work, you can use the hotel’s 24-hour business center.

Browse Hotel Blake Timeshares for Sale or Rent.

Hilton Grand Vacations Chicago Downtown

Hilton Grand Vacations Chicago Downtown offers its guests an urban retreat in the Magnificent Mile district. This area is full of things to do and see, including shopping at over 450 retailers. The district is also a great spot to stay for foodies because there are hundreds of restaurants to choose from. Some restaurants even offer rooftop patios, so you’ll get to enjoy a meal with incredible views of downtown Chicago. This HGVC resort is just a short walk from where you can jump on one of Chicago’s famous river cruises. Enjoy the resort’s seasonal rooftop pool or the year-round fitness center. The resort offers stylish studios and one-bedroom suites, some of which offer stunning views!

Buy or Rent Chicago Timeshare

Are you ready to buy or rent a Chicago timeshare? If so, you’ve come to the right place! Firstly, browse our selection of timeshares for sale or rent in Chicago. Then, when you’ve found one that you love, simply make an offer! Don’t worry if you have questions because we are here to help! Our team of timeshare experts has the connections and experience to make this process seamless, so contact us! Call 1(800) 213-7733 today!

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