Chicago is famous for its beautiful skyline, delicious deep-dish pizza, and legendary architecture. But beyond the typical must-see list, there are so many unique things to do in Chicago waiting to be discovered. Some of the most memorable experiences aren’t the big-name attractions; they’re the off-the-beaten-path activities, local favorites, and Chicago hidden gems tucked throughout the city’s diverse neighborhoods. From unique Chicago tours to unexpected adventures, these experiences offer a fun, authentic, and unforgettable way to explore the city.
Chicago Hidden Gems & Experiences
Chicago Sports Museum
On the seventh floor of the Water Tower Place, inside of Harry Caray’s 7th Inning Stretch Restaurant, you’ll find a trove of Chicago sports history. The museum combines skill challenges, hi-tech simulated experiences with unique sports memorabilia and an impressive collection of game-used treasures and other artifacts.
- Located in Water Tower Place on the Magnificent Mile (Michigan Ave.)
- Visit year-round, occasionally closed for private events. Check the calendar.
- $10 general admission. Guests of the adjacent Harry Caray’s 7th Inning Stretch receive free admission with minimum purchase.
- Locals, tourists, families, event planners and sports fans of all ages enjoy the Chicago Sports Museum.
Lincoln Park Conservatory
The Lincoln Park Zoo and Farm at the Zoo are both very popular. They sometimes overshadow the unique experience at the Lincoln Park Conservatory. This Chicago hidden gem hosts a feast for the senses and is climate-controlled year-round. From the lush fern room to the chocolate orchids to the seasonal flower show, there is something for everyone.
- Located in Lincoln Park, northwest of the Lincoln Park Zoo, south of Fullerton Ave.
- Visit year-round seasonal shows that rotate throughout the year. There is always something beautiful blooming. Check online for updates on shows.
- Always free! Donations are recommended and reservations required.
- Locals, Tourists, school groups, date nights or proposals all love the conservatory!
Graceland Cemetery
Graceland Cemetery has more than just the dearly departed. Visit during open hours and receive a complimentary handbook and a self-guided unique Chicago tour to visit sculptures and learn vast history while on a quiet, idyllic walk off the beaten path through Chicago’s history.
- Located in the Uptown neighborhood at Clark St. & Irving Park Rd.
- Visit year-round. Open daily from 8am or 9am until 4pm.
- Always free! Please be respectful of those peacefully resting and their families.
- If you enjoy cemetery walks, then this is the place for you. There is so much history and unique learning opportunities at this sacred place to visit in Chicago.
The Nature Boardwalk at Lincoln Park
Wind your way off the beaten path and through the labyrinth of walkways along the southern border of the Lincoln Park Zoo until you reach the Honeycomb for that special photo op, which includes both nature and the gorgeous Chicago Skyline. Begin your journey at the historic Café Brauer (open since 1900) and walk under the bridge on a unique path around a lagoon, surrounded by wildflowers at this Chicago hidden gem, The Honeycomb aka The People’s Gas Pavillion.
- Located in Lincoln Park, south of the Lincoln Park Zoo.
- Visit year-round – best to visit when the flowers are in bloom.
- Always free! Enjoy nature and the city skyline.
- If you enjoy nature walks, then this is the place for you. Discover something new each time you wander at this unique place to visit in Chicago.
Pedway
Throughout the Central Business District in the Loop neighborhood, travel through a labyrinth of tunnels below the city known as the Pedway. Shield your commute from inclement weather and enjoy the murals, history, and unique stops that cover approximately 5 miles.
- Located in the Loop, with many access points. Some easy access points are Block 37, Millennium Station, and Macy’s.
- Visit year-round – best to visit during inclement weather.
- Always free! Enjoy unique stops along the route and navigate maps on your way.
- This walkway is best for those with an adventurous spirit and who enjoy walking through tunnels on this urban spelunking experience.
Pizza Class
Visit the historic landmark building at 35 E Ohio St and learn how to make the original deep-dish pizza at Pizzeria Uno or one block north at Pizzeria Due. Tour the buildings, make pizza, learn about the history and eat pizza. This one-of-a-kind experience at the original home of Chicago deep-dish pizza is high on the list of unique things to do in Chicago.
- River North neighborhood
- Classes available year-round. Check the schedule online to book in advance.
- $59 + tax per ticket
- Best for couples, families and pizza lovers
Unique Chicago Tours & Museums
From bus tours to unique museum tours, guided experiences offer a deeper way to explore Chicago. These Chicago tours turn sightseeing into storytelling and help you and your group uncover the city’s history, neighborhoods, and hidden gems.
Chicago Crime Tour or Night Crimes Tour
Explore Chicago’s gangsters, criminals and mobsters on a bus tour through 6 neighborhoods. Most of the tour is on the bus, however, there are stops off the bus as well. Visit historic crime scenes.
- Crime history tour by bus
- Streeterville, Lincoln Park, Old Town, River North, Loop and Gold Coast neighborhoods
- Chicago Crime Tour: 1.5-2 hours | Night Crimes Tour: 2-2.5 hours
- All ages are welcome. Great for crime scene investigators.
- Expert professional tour guides are passionate storytellers. Each tour is special and unique.
- Tours run year-round. Check the schedule and book online.
International Museum of Surgical Science
This historic building is a sight to behold and overlooks beautiful views of Lake Michigan. From art galleries to a live demonstration of an amputation, this museum has something for everyone. This unique Chicago tour is a dynamic combination of art, history & science. Check out their schedule online for upcoming programs.
- Learn about the history of surgery around the world, technological advancements and the history of surgery/anesthesia and more.
- Gold Coast neighborhood
- Guided tours are approximately 1-1.5 hours with the live demo. Budget at least 2 hours if you want extra time to explore on your own and visit the gift shop.
- Recommended for ages 12+, minimum group size of 10 people
- Tour guides are either work in the medical field or are retired medical professionals.
Money Museum
The Federal Reserve Bank of Chicago’s Money Museum is one of the most unique things to do in the Windy City. Learn about economics, money, and the role of the Federal Reserve. Try your hand at detecting counterfeit notes, learn what a million dollars looks like, and view rare currency on display at one of their exhibits.
- Learn about money, economics and history.
- Loop neighborhood
- 60–90-minute group tours must be booked at least 3 weeks in advance
- Recommended for ages 12+, at least 15 people. Closed Sat/Sun & national holidays.
- This is one of 12 Federal Reserve Banks in the USA and serves 5 states.
Unique Chicago Neighborhoods
Explore outside of downtown Chicago and check out special artistic murals and culturally diverse spaces. There are so many wonderful things to do in Chicago, this list is a small sample of some unique things to do off the beaten path.
Chinatown
Do you like Chinese food? Boba? Souvenirs? Chinatown has it all, including a visitor’s center, mosaic art, and bronze animal statues that symbolize Chinese culture, virtues, and fortunes. The unique public art, dim sum, Chinese medicine, and more all make up this unique Chicago neighborhood. Try taking a water taxi ride from the Michigan Ave Bridge or the CTA Chicago Red Line for an experience you will remember forever.
Pilsen
Street art – including extensive murals – Hispanic culture, and history are just a few of the reasons Pilsen was named one of the coolest neighborhoods in the world. Authentic Mexican cuisine (like El Milagro) is easy to enjoy along with the colorful street art and National Museum of Mexican Art.
Andersonville
Explore historic landmark buildings, uncover history in the Swedish American Museum, or enjoy a show at the Chicago Magic Lounge. Also, try some sweet or savory Swedish American breakfast at the historic Svea Restaurant, established in 1932, then walk down Clark St to shop at the local small businesses. There is truly something for everyone in the quaint and unique Andersonville neighborhood.
Little Italy
Taylor St has long been known for its Italian cuisine and culture. Dine at many traditional and modern Italian eateries, visit the local Italian grocer filled with imports and fresh pastas and homemade sauces, or sample the seasonal favorite Italian ice at Mario’s Italian Lemonade. Mario’s has every flavor imaginable of Italian ice with little chunks of fresh lemon rind. Prepare for a long line on a hot day for this Italian delicacy. While cooling down with your favorite Italian ice, chill in a local park, shop at a comic bookstore, or visit any of the other local small businesses along Taylor St in Little Italy.
Chicago is full of surprises if you know where to look. Step outside of downtown and visit hidden gems, hear local stories, learn about local legends, and create memorable experiences that feel uniquely personal. From clandestine speakeasies (Pizzeria Uno was a speakeasy during Prohibition) tucked away in historic neighborhoods to vibrant, off-the-beaten-path cultural institutions and serene, unexpected green spaces, the best experiences are often found beyond a guidebook!
