Things to do in Chicago

20 Hidden Gems in Chicago You Must See

As one of the largest cities in North America, Chicago has plenty of hidden gems to discover.

A day in Chicago calls to mind fond images of cheesy deep-dish pizza and awe-inspiring architecture. For those looking for things to do in Chicago, we've got several excursions good enough to share. Explore 20 hidden treasures in Chicago, including world-class museums, public parks and incredible views that deserve a spot on your itinerary.

Hyde Park

Hyde Park, site of the Chicago World's Fair and home to Nobel Prize winners, boasts the Museum of Science and Industry. The Museum of Science and Industry, formerly the Palace of Fine Arts, is the sole surviving structure from the 1893 World's Fair. It stands as a testament to the fair's history and legacy.

1. Promontory Point

On the lakeside edge of Chicago's Burnham Park is a man-made island with a view to rival any skyscraping observation deck. At Promontory Point, the lush green grass gently slopes down to a large stone staircase leading into Lake Michigan. This architecturally historic lookout is one of Chicago's lesser-known gems. It offers stunning views of the city’s skyline.

Photographer: Moses P

The Loop

A creative hot spot, the Loop houses iconic art installations and annual events such as Lollapalooza. For those who revel in the city’s vibrant culture, exploring the Loop is among the most unique things to do in Chicago.

2. Money Museum at the Federal Reserve Bank

Who knew learning about money could be just as fun as spending it? The Federal Reserve Bank of Chicago's Money Museum presents the history behind the currency used daily.The museum features exhibits on currency history and inflation, and entry is free. Interactive displays teach counterfeit bill detection and showcase a ton-heavy $1 million cube.

3. The International Museum of Surgical Science

The International Museum of Surgical Science, unique in its focus on surgery, showcases the history of medical development. Its collection, housed in a lakefront mansion, includes a range of medical artifacts and fine art with medical themes. Exploring the museum, visitors can immerse themselves in the history of medical achievements. They also witness the progress of modern medicine.

4. Millennium Park's Hidden Garden

Lurie Garden, a hidden gem, conceals itself from the city behind two 15-foot-tall hedges, accessible through a secluded path. Visitors entering the garden find themselves surrounded by lush trees and vibrant flowers. The garden is strategically planted to shield the

Photographer: STLJB

5. ROOF on theWit

When you've had your fill of hidden gardens, dive into the deep end of civilization with a trip to ROOF on theWit. This renowned bar, located 27 stories high, embodies Chicago's nightlife with its outstanding atmosphere. It features an excellent selection of drinks and food options. Daytime brings sunshine with handcrafted cocktails and a refined menu. Nighttime offers the vibrant ROOF dance floor, energetic music, and skyline views.


This bustling neighborhood immerses visitors in a culture vibrant and ripe for exploration.

Photographer: Kim Lewis Photography

6. Zodiac Square

Chicago's Chinatown is a lively, must-see area for an authentic city experience. Begin your visit at Zodiac Square, a two-story outdoor mall with the Cultural Center and a stunning glass mural. The square features twelve bronze zodiac statues, each symbolizing unique characteristics. Explore and learn about each one.


A trendy spot for restaurants and nightlife, Bucktown has plenty of uncovered ground to dive into. Amidst the exceptional boutiques, don't miss a chance to enjoy a superb cup of coffee and a snack at Red June Cafe.

Photographer: Jess Kraft

7. The Magic Parlour

Witness unbelievable tricks and mind readings at The Magic Parlour. It is hosted by third-generation magician Dennis Watkins. This intimate performance offers a close-up view of each sleight, from pulling razor blades from his mouth to duct-taping his eyes shut. Settle into the retro showroom, and let your sense of wonder soar.

8. Big Monster Toys’ Monster Door

Big Monster Toys, a Chicago-based toy company, creates cherished playthings for children. But what draws daily visitors is the unique photo opportunity at the headquarters. A massive, bright yellow door on the building's facade, with a giant silver doorknob, turns guests into pipsqueaks. The door has become a local legend and now serves as the substitute logo for the toymakers inside.

9. Challengers Comics + Conversation

According to Challengers Comics + Conversation fosters a sense of community among comic enthusiasts. Here, you can engage in unique conversations while exploring a vast collection of comics, manga, and toys. It's a place to embrace your inner geek and shed your alter ego. If your timing is right, you might even catch live in-store events with your favorite authors, making for memorable conversations.

Old Town

This historic neighborhood is popular for its Victorian-era architecture and small-town charm, offering a delightful escape in bustling Chicago. Old Town's tree-lined streets feature charming boutiques and cozy cafés. Notable spots include Gepperth’s Meat Market, with a century of history, Judy Maxwell Home, blending general store charm with an art gallery, and Old Town Pour House, a haven for craft beer lovers with 90 beers on tap.

10. Twin Anchors

Chicago lore has it that Twin Anchors was Frank Sinatra's favorite spot for a pre-concert meal in the Windy City. Ol' Blue Eyes supposedly couldn't get enough of the tavern's specialty ribs recipe, which they're still serving to ravenous customers decades later. Now in its 90th year, Twin Anchors remains committed to its time-honored traditions, slow-cooking each rack until it's fall-off-the-bone tender and slathering it in a river of house-made sauce. Just ask for extra napkins.

West Town

Though unassuming at first glance, West Town is the clandestine home to some of Chicago's tastiest treats. Its dining landscape offers an adventure with every bite, from the vibrant Latin American flavors at Dell Rooster to the soul-nourishing comfort of Soule, the exceptional Filipino cuisine at Kasama, and the German-inflected, steak-focused offerings of Boeufhaus. Each establishment in West Town turns dining into an exploratory event.

11. Hoosier Mama Pie Company

When founder Paula Haney started selling her pies at a Chicago farmer's market, she never anticipated it would turn into a full-blown brick-and-mortar business. Though still unknown to crowds of tourists, Hoosier Mama Pie Company is recognized among a growing branch of Chicagoans as the best pie shop in the city. Relying on traditional baking techniques, Hoosier Mama pies come with a buttery, flaky crust encasing the gooey filling within. Classic sweet flavors, such as blueberry and apple, adorn the menu, but the savory chicken pot pie is lauded for its sublimely creamy interior dotted with fresh vegetables.


Once a popular destination for Swedish immigrants, Andersonville's eclectic food scene reflects its diverse history. This neighborhood is a treasure trove for foodies looking to indulge in Chicago restaurants that offer a taste of the city’s rich culinary diversity. To add a touch of enchantment to your visit, don't miss the Chicago Magic Lounge, renowned for its captivating performances and magical ambiance.

12. Andersonville's Food Crawl

The Taste of Andersonville Food Crawl is an annual event that locals look forward to all year long. For one night only, this event showcases Andersonville's shining collection of local restaurants, each serving up dishes that are both innovative and undeniably delicious. Partake in the culinary celebration by choosing your route and sampling the offering laid before you. Your taste buds will rejoice at the mere sight of crispy-crunchy fish and chips, cheesy wood-fired pizza, and steaming mugs of hot chocolate topped with handmade marshmallows.

Wicker Park

Wicker Park in Chicago, renowned for its chic boutiques and fashion scene, also boasts notable venues like the Salt Shed, a contemporary music space with unique culinary offerings, and the historic Chopin Theatre, famous for its diverse range of artistic events. These destinations, together with Wicker Park's niche shopping experiences, contribute to its reputation as a vibrant, picture-worthy neighborhood, so grab .

13. The Violet Hour

Chicago bars have come a long way since the days of Prohibition, but some gems are best kept hidden. In Wicker Park across the street from the neighborhood taqueria lies a large wooden door. Open it, and step into the enigmatic halls of The Violet Hour, an award-winning bar that shies away from the attention it deserves. Lit by candlelight, the sleek and spare atmosphere of this bar will have you convinced you really have entered a clandestine world of secrets and intrigue. Sip on specialty shaken cocktails such as the Lizzy Grant, topped with scorched vanilla demerara. Or stick to the classics, and order an Old Fashioned to rival any other.


Streeterville, a vibrant lakefront neighborhood, is home to countless attractions for all ages. The Winter Jazz Club offers classic live jazz in an intimate setting, while Navy Pier is a year-round destination with fireworks, live music, cruises, and events. The Magnificent Mile, also known as Michigan Avenue, boasts numerous retailers and a renowned culinary scene. These attractions make Streeterville a dynamic community hub for residents and visitors alike.

14. Cindy's Rooftop

From its perch on the Chicago Athletic Association, Cindy's Rooftop has long served up sophisticated fare against a remarkable backdrop. Peer through the walls of this glass atrium at some of the city's famed attractions on the streets below, including the verdant expanse of Millennium Park and The Bean in its shining splendor. With skyscrapers as your companions, take in the landscape from above as you sip handcrafted cocktails and nibble on fabulous dishes, including patatas bravas, trout over gazpacho, and freshly baked chocolate chip cookies.

Gold Coast

Also on the banks of Lake Michigan, the Gold Coast is a picturesque neighborhood with luxury restaurants, coffee shops, and shopping experiences.

Photographer: James Andrews 1

15. Thorne Miniature Rooms

Chicago architecture can touch the sky, but some designers have found the beauty in thinking small — miniature, in fact. This was the case for Narcissa Niblack Thorne and her team, who all created the Thorne Miniature Rooms inside the Art Institute of Chicago. With a delicate touch and a verve for interior design, the team crafted 68 teeny-tiny rooms that now make up a powerful display of whimsy and intricacy. Take a peek into each room for an unusual museum-going experience that wows just as much as its larger counterparts.

South Deering

On Chicago's far South Side, this neighborhood houses a phenomenal restaurant serving up fare plucked straight from the water.

16. Calumet Fisheries

Smoking fish is a labor of love, and Calumet Fisheries has turned the technique into an art form. Lodged just feet from the water in a humble shop, Calumet chefs brine and smoke the fish straight from the water to coax out the naturally delicious flavors lurking inside. You'll smell the earthy scent of smoldering oak wood before you've even opened the door and laid your eyes on the offerings within, which are crusted with garlic and black pepper. No indoor seating means this is a meal best eaten hot in the car or carried to the nearby drawbridge and eaten where a few scenes of The Blues Brothers were shot.

17. Margie's Candies

Mountains of sugar-sweet ice cream, whipped cream clouds, and chocolate fudge rivers are what's in store for you at Margie's Candies. For nearly 100 years, the shop, which has locations near Lincoln Square and Bucktown, has delighted Chicagoans with its confectionery spread, with staff churning ice cream and dipping chocolates by hand in its backroom kitchen. Stop here for a taste of homemade candy, or order a giant banana split still served in a vintage white clamshell bowl.

18. Chicago's "Bat Cave"

The Bat Cave is really a secret underground roadway once frequented by shuttle buses heading to a nearby convention center. But for history buffs, it doubles as a slightly spooky place to explore an urban thoroughfare abandoned by time. While you might encounter one of the few remaining delivery trucks that frequent the tunnel, the "Bat Cave" offers an eerie glimpse into once-bustling city spaces now forgotten.

19. Historic Hotel Tours

Windy City hotels are popular sites for visiting tourists observing from the street. But the real hidden gems of Chicago can only be seen from inside, where architectural intricacies combine to create marvelous lobbies, elevators, and stairwells. Book a tour at the Palmer House for an intimate look at the city's oldest operating hotel with its cathedral-like domes and gothic detailing. The Drake Hotel, the Blackstone, and the Staypineapple Chicago are other historic resting spots that history lovers and architectural fanatics will swoon over.

20. Chicago's Speakeasy Bars

In the 1920s, Prohibition prompted a speakeasy boom where patrons could drink and socialize while avoiding detection. And while many of these undercover bars have been lost to time, Chicagoans still flock to their modern equivalents, thrilled by the novelty of breaking the rules for a stiff drink. Spots such as The Drifter are real-deal speakeasies preserved for decades and still supply the public with freshly shaken cocktails. For a more modern take on the speakeasy, head to Pigtail for drinks served alongside fried pig ears.

Uncover Chicago's Hidden Gems

For the people who don't shy away from the strange, these Chicago hidden gems are the perfect off-beat activities to turn an average day in the city into a search for secret wonders. For an astonishing experience you don't have to hunt for, head to a theater near you to catch our latest masterpiece. Complete with jaw-dropping acrobatic feats and moving storylines, these performances are packed with imagination-bending sights that will have you literally hanging off the edge of your seat. At our shows, the only thing you can expect is the unexpected. Book your tickets today and experience the spectacular performance for yourself.

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