Hidden Gems of Chicago: Exploring the City Off the Beaten Path

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December 16, 2020
Chicago off the beaten path

From the Art Institute of Chicago with its regal lion statue to the ever-famous Bean in Millennium Park, there is always something to do and see in Chicago. However, while popular tourist attractions are always a go-to, you truly haven’t experienced the city to the fullest unless you’ve explored like a local—and that often means going off the beaten path.

Our friends at FLATS put together a list of 7 lesser-known attractions that will help you make the most out of your time in The Windy City.

Off the beaten path things to do in Chicago

1. Heritage Outpost Coffee

To fuel your day of fun, Heritage Outpost is the perfect place to get your caffeine fix and pick up a sweet treat or two. These cozy coffee houses found throughout the city not only offer locally roasted coffee but a relaxing ambiance that blends contemporary finishes with warm wood accents. Pair that with their service that creates locally crafted, handmade bicycles, and it is easy to see why these spots are well-loved among locals.

Heritage Outpost has multiple locations, including Lakeview, River North, and Uptown inside The Lawrence House—a former luxury hotel oozing with vintage charm that has been converted into an apartment building.

2. Room 13

Through a discreet alleyway entrance to the left of the Old Chicago Inn you will be transported back to the roaring ’20s. After knocking and giving your password to the doorman you can step in and enjoy the Prohibition era-inspired speakeasy called Room 13. Here you can sip prohibition-style cocktails and explore relics from the past, like old slot machines.

How do you know the password? Passwords are obtained through membership or by being a guest at the Old Chicago Inn.

Located at 3222 N Sheffield Ave.

3. Headquarters Beercade

Dedicated to fun, craft beer, and whimsical cocktail creations, you won’t be disappointed with Headquarters Beercade. They offer over 65 arcade games throughout their venue, and that isn’t even the best part—they are all free to play! Overall, it is an exceptional bar to enjoy a night on the town in River North.

Located at 213 W Institute Pl.

4. National Museum of Mexican Art

With so many nationally recognized museums like the Art Institute of Chicago, the Museum of Science and Industry, and the Chicago Museum of Contemporary Art, many smaller museums get overlooked. And this is often the case with the National Museum of Mexican Art. This museum nestled in The Lower East Side in Pilsen exemplifies the culture of the area that many Mexican immigrants made their home in Chicago’s early days. This free museum has over 10,000 pieces in a permanent collection that will steep you in the Mexican culture through various art forms such as paintings, textile art, and sculptures.

Located at 1852 W 19th St.

Want to dive deeper into the Mexican heritage that makes the area so unique? Walk the streets to admire the vivid murals and street art in Pilsen that reflect Mayan and Aztec culture. 16th street along the train tracks has the largest concentration and is an absolute must-see for any art lover.

5. Big Monster Toys

Both children and kids at heart will love Big Monster Toys. This toy and game design studio knows how to catch attention with a giant yellow door on its exterior that sports a large monster peeking from the window. This ginormous door will make you feel like an ant and provides a unique photo opportunity. Inside you will find more supersized fun with a building-wide elevated train set fitted with staff-designed cars and a towering stuffed giraffe.

Located at 21 S Racine Ave.

6. Apollo Theatre

While the Apollo Theatre in Lincoln Park itself may not exactly be a hidden gem, some of its productions certainly are. Baby Wants Candy springs to mind, an improv musical that very few have heard of, yet it has garnered rave reviews.

In this park that spans 1,208 acres you will also find public beaches, trails for walking and biking, and a slew of recreational activities. Popular tourist attractions in the area include the Lincoln Park Zoo and Lincoln Park Conservatory.

Located at 2540 N Lincoln Ave.

7. The Original Rainbow Cone

It is no secret that deep dish pizza hails from the Windy City, but that isn’t the only food invented in Chicago. There is sweet and salty Garrett Popcorn, mouthwatering Vienna Beef Chicago style hot dogs, and the extra colorful Original Rainbow Cone—a treat that has remained the same since its inception in 1926. This bright cone comes layered in chocolate, strawberry, Palmer House, pistachio, and orange sherbet flavors to create a taste that will blow your tastebuds away. The Original Rainbow Cone is the perfect treat to cool you off on a hot summer day, but 100% worth it even in colder weather!

The original location is 9233 S Western Ave, with an additional shop on 600 E Grand Ave.

There is something for everyone in Chicago and finding an activity that suits your interests off the beaten path will help make your time exploring the city all the more memorable. Whether that means grabbing a drink at a prohibition-inspired speakeasy or scooping up a colorful snack at The Original Cone, you will be happy you did!

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