Everyone needs a break now and again. Whether you’re on a budget and looking to save money on travel or ready for a quick refresh over the weekend, a staycation is a great way to have the best of both worlds. Chicago is an always-changing city, ready to offer each resident and visitor a unique experience whenever they enter the Loop. If you’re ready to plan a staycation in the City That Works, we’ve gathered the best ways for locals to enjoy their time off.

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Watch a Broadway show

Chicago is home to world-class actors as they take to the stage to perform some of the best plays Broadway has to offer. With options like “Hamilton”, “Harry Potter and the Cursed Child”, and “Wicked”, there is always something exciting going on at the Chicago stages. Even if you’ve been to a show before, each performance is a unique experience that locals can enjoy attending again and again, discovering new favorite shows as they enjoy the talent.

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Visit the Wild mile

One of The Windy City's newest greenspaces is a must-see for tourists and locals alike. The Wild Mile is a floating park, stretching along the Chicago River and home to wildlife right in the heart of the city. This is a breath of fresh air, ready to create a one-of-a-kind experience for visitors again and again, with new flowers always popping up and helping to clean the river for generations to come. Even if you’ve been to the river before, this is a completely new way to experience the beauty time and time again.

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Shop farmers markets

Supporting local makers and growers is a great way to take in the culture of this rich city. Farmers markets may attract tourists, but they are also the perfect place for locals to find a favorite small business to frequent as they go about their lives every day. Full of discovery and curiosity, each farmers market changes their offerings no matter how many times you attend.

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Watch a movie at Rooftop Cinema Club

Streaming classics like “The Devil Wears Prada” “Harry Potter” and “Inception”, there is never a bad night to visit this outdoor movie theater. Enjoy your popcorn under the stars as you watch from a massive screen atop a soaring roof in the city, which is sure to be an experience you won’t find elsewhere. Locals enjoy the atmosphere and can be sure that each attendance is worth their time.

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Cheer on the Chicago Cubs

“Da Bears” stadium is an iconic landmark and one that people travel from near and far to experience. For a Chicagoan, a game might be a little more exciting as they are familiar with the traditions and have a little more pride in their home team. Baseball provides a game that leaves you on the edge of your seat each time, with new twists and turns occurring each inning. No matter who their opponent, it’s always a great day at the ballpark when you’re sporting the blue and red.

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Stay in an imaginative hotel

The key element to making a staycation different from any other day in the city is taking a night away from your home to relax and unwind. Choosing a hotel that is both close to the action and that will make your experience unique is important. Rather than staying at a hotel, you can find anywhere, finding one with a theme that permeates the essence of your stay creates lasting memories and makes your mini-vacation an experience you’ll crave again and again. Be sure to check out Trip-advisor and other listings to find the hotel that stands out from the rest and book a room in your beloved city. 

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Come for the fun, stay for the views

Chicago is a city with never-ending offerings to enjoy. Whether you’re a big-city aficionado or you love to collect new experiences, there’s something for everyone here. Locals can continue to discover ways to enjoy the attractions, no matter how long they live here. If you’re ready to book a staycation and take a short break from your daily life without leaving the city you love, click here to learn more about our boutique hotel in the heart of it all.