Chicago is an iconic hub of culture, art, and amazing street food. But there’s a lot more than jazz music and deep-dish pizza to be discovered in the Windy City, starting with these eight hidden gems!

1. Wabash Arts Corridor, South Loop

Discover Chicago’s most beautiful— and most secret— art at the Wabash Arts Corridor. Often referred to as a “living canvas,” this mile-long street is adorned with brilliant murals on the sides of apartment buildings and within parking lots. It’s ever-expanding too, with new art being added frequently. 


2. Sundae Stop, Lake View East 

This incredible ice cream shop is the definition of hidden in plain sight. Modeled after Chicago train stations, steps away from the Belmont Red/Purple/Brown stop, and complete with a replica train, it wouldn’t be surprising if you overlooked this quaint shop. But with delicious homemade ice cream and crepes in fascinating flavors, you’ll be well-served by stepping inside this faux-train station. 


3. Walgreens in Noel State Bank, Wicker Park

It’s historical architecture! It’s a bank! It’s a … Walgreens? This beautiful bank in Wicker Park from the 1920s was converted into a Walgreens in 2012, providing the city of Chicago with the most visually stunning and interesting pharmacy around. Take a trip to Walgreens to check out the stunning architecture and maybe grab some snacks. And don’t forget about the Vitamin Vault, which is exactly what it sounds like. 


READ MORE: Your Foolproof Guide To Visiting Chicago

4.  The Secret Mermaid, Oakland

By the Oakwood-41st Street Beach, along the waterfront, lies a hidden sculpture. Created by four artists who secretly carved it for nine consecutive nights in 1968, the Secret Mermaid is both a gorgeous sculpture and a fun secret that only the locals (and now you) know about.


5. Gin Alley, Fulton Market

This stunning piece of Fulton Market contains everything you could need from life — and more! With restaurants featuring various cuisines, a collection of vibrant murals, and a vast range of local businesses to shop your heart out at, you’ll never be bored in this beautiful area. The cobblestone streets and string lights give it a charming atmosphere. You’ll want to spend your whole trip here!


6. Quimby’s Bookstore, Wicker Park

Independent bookstores are the under-recognized artistic heart of many cities, and Quimby’s Bookstore is no exception. The bookstore specializes in graphic novels, independently published works, and anything unconventional or out of the ordinary. You’re sure to find a literary work to suit your taste, and the store often has events and readings, too!


READ MORE: Feeling Snackish? The Best Late-Night Bites In Chicago

7. Utopian Tailgate, Old Town Triangle

There’s no simple way to describe Utopian Tailgate. It’s a rooftop bar with a full restaurant, which is pretty standard for a big city, but there’s also live music, quirky decor, and a vast variety of fun games. Upon arrival, prepare for eclectic cocktails, bright colors, unforgettable views, and even a disco dance party— all in the 10,000 square foot area. 

8. Dat Donut, East Chatham

Chicago’s greatest donut shop has been operating for 25 years, and while it’s famous among locals, it’s certainly a hidden gem for tourists. Their donuts, hand-cut daily, are the delicious centerpiece of the menu, though they also offer a variety of breakfast items and beverages. What they’re most famous for is The Big Dat Donut, a massive donut that dwarfs all others in comparison.  

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