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7 Hidden Gems in Chicago You Can't Miss

September 15, 2023 By CityPASS

A trip to Chicago will likely include a few must-dos, like taking a selfie at The Bean and heading out for a Chicago river tour. But you should also leave time to discover some of the Windy City's plethora of hidden treasures. These hidden gems in Chicago may not be in your guidebook, but they should definitely be on your itinerary.

What To Expect When Visiting Chicago

Chicago is both steeped in history and flashing in modernity nearly everywhere you look. Sleek towers dot the skyline alongside iconic monuments like Navy Pier and Art Institute Chicago. Chicago certainly has its finger on the pulse of innovation so there are always new things to see, do, and discover.

This city has found the perfect balance between flashy cityscape and serene green space. Some of Chicago biggest attractions are the city's numerous public parks and gardens — especially in the warmer months. During any given weekend, you'll find some kind of festival celebrating art, food, music, or culture. Chicago is a city that loves to celebrate its people and its history, and both are great reasons to throw a party.

Whether you're heading to the city for a fulfilling solo escape or to celebrate with friends or family, a trip to Chicago will surely be a memorable one.

Our Top Picks for Hidden Gems in Chicago That Are Worth a Visit

Even if you're familiar with the most historic places in Chicago, you might be surprised at the number of hidden gems in downtown Chicago. Here are some cool places off the usual tourist track.

Travel Back to the 1920s at The Library Speakeasy

The first of our Chicago hidden gems is a sneaky speakeasy tucked away in the lively River North neighborhood. Gilt Bar is a popular eatery that serves classic cocktails and contemporary American cuisine. While this place is worth a visit on its own, the real draw is the Chicago speakeasy that's hidden in the basement.

Going through a side door, you will descend into The Library, a speakeasy reminiscent of the days when Chicago was famous for distilling gin. Velvet booths, chandeliers, and a wide variety of books add to the vintage atmosphere. Seating is limited in this intimate space so it's best to make a reservation.

Visit Maxwell Street Market for a Local Experience

The Maxwell Street Market is located in the historic Chicago neighborhood of Near West Side, one of the city's oldest residential areas. This is the birthplace of Chicago blues and the famous Maxwell Street Polish sausage sandwich.

The market takes place most Sunday mornings from late spring to the autumn. Here, you can browse a wide variety of handmade crafts, listen to live music, and sample some of the city's best street food. Maxwell Street Market is family-friendly and full of fun.

Enjoy Magic and Craft Cocktails at Chicago Magic Lounge

Chicago Magic Lounge is a perfect spot to kick back, relax, and have a laugh. Step through a secret laundry entrance and enter a world of mystery and magic. Experience a magic show, enjoy a cocktail, and nibble on some snacks. This is a great spot for a date or to spend with a group of friends.

Wander Through Garden of the Phoenix

For the world's fair in Chicago in 1893, the government of Japan created the Garden of the Phoenix, a Japanese Garden. Within Jackson Park, the Garden of the Phoenix symbolically represents the city rising from the ashes after the Great Chicago Fire in 1871.

Visitors can stop by the koi pond in the outdoor park, marvel at the Japanese plants and cherry blossoms, and even see a sculpture created by Yoko Ono. While the garden is always a wonder, the most magical time to visit is during the one week in late April when the cherry blossoms are in full bloom.

Appreciate Secret Views of the Chicago Riverwalk at Southbank Park

A fairly modern addition to the city is the Chicago Riverwalk. It spans a quarter mile of the south bank of the Chicago River, which flows into Lake Michigan. It's the perfect spot to picnic, go for a stroll, or even launch a kayak.

Along the Riverwalk, there's a great selection of upscale cocktail lounges, restaurants, and dive bars. It's not unusual to see groups of people relaxing on the shores of the river and taking in the beautiful views.

Enjoy a Movie at the Music Box Theatre

The Music Box Theatre is a one-of-a-kind attraction in Chicago. It was built in 1929 and retains much of its original charm and decor. With only one screen, the theater shows just one movie at a time. You can see current blockbuster movies as well as special showings of holiday and seasonal films. There are even a number of sing-a-longs that you can attend with classics like The Sound of Music and White Christmas.

Explore Chicago's Iconic Chinatown

Step into a whole new world in Chicago's Chinatown on the city's South Side. It holds more than 100 years of history and is home to a third of Chicago's Chinese population. This makes it one of the largest concentrations of Chinese Americans in the U.S.

The streets are lined with gift shops, restaurants, grocery stores, and even traditional Chinese medicine shops. Stop to shop, enjoy an authentic meal, and check out the beautiful murals and architecture that you won't find anywhere else in the city.

Discover More Chicago Hot Spots With CityPASS®

Want to know one of the real hidden gems of Chicago? A Chicago CityPASS® ticket that lets you save up to on Chicago's top things to do. With two different options to choose from, you can explore either three or five of the best downtown Chicago hot spots. Discover big savings and exciting attractions in the Windy City with your CityPASS® ticket today.

Chicago Lodging

To get the most out of your stay in Chicago, we recommend finding lodging near Chicago's top attractions. Use this map to find the right lodging for you:

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