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.
1. Promontory Point
Promontory Point, a lush green grassy area, gently slopes down to a large stone staircase leading into Lake Michigan. On the lakeside edge of Chicago's Burnham Park is a man-made island with a view to rival any skyscraping observation deck.
- Type: Public park
- Why It’s a Gem: This peaceful spot overlooking the lake has a wonderful view of the city’s skyline.
- Address: 5491 S DuSable Lake Shore Dr, Chicago
- Cost: Free
- Vibe: Tranquil and scenic
2. Money Museum at the Federal Reserve Bank
The Money Museum, part of the Federal Reserve Bank of Chicago, presents the history behind the currency used daily. The museum features exhibits on currency history and inflation, and entry is free. Who knew learning about money could be just as fun as spending it?
- Type: Museum
- Why It’s a Gem: Get a hands-on look at U.S. money history.
- Address: 230 S LaSalle St, Chicago
- Cost: Free
- Vibe: Educational and insightful
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, medical achievements and progress of modern medicine. Its collection, housed in a lakefront mansion, includes a range of medical artifacts and fine art with medical themes. This activity is among the most unique things to do in Chicago.
- Type: Museum
- Why It’s a Gem: View rare surgical tools of medicine's past in a historic mansion.
- Address: 1524 N Lake Shore Dr, Chicago
- Cost: $25 adults / $18 seniors & students / $15 children age 4-13
- Vibe: Intriguing and historical
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.
- Type: Public garden
- Why It’s a Gem: This quiet oasis offers respite amid the downtown bustle.
- Address: 220 E Monroe St, Chicago
- Cost: Free
- Vibe: Serene and enchanting
5. ROOF on theWit
ROOF on theWit is where you go when you’ve had your fill of hidden gardens. This renowned bar, located 27 stories high, embodies Chicago's nightlife with its outstanding atmosphere. It features an excellent selection of handcrafted drinks and a refined food menu.
- Type: Rooftop bar & lounge
- Why It’s a Gem: Enjoy an all-season skyline view under the retractable roof of this high-perched lounge.
- Address: 201 N State St 27th Floor, Chicago
- Cost: Varies per item
- Vibe: Chic and energetic
Wow-Worthy Circus Acts!
Get ready to be amazed in Chicago! Jaw-dropping Cirque du Soleil performances are just a click away.
6. Zodiac Square
Zodiac Square in Chicago's Chinatown is a lively, must-see area for an authentic city experience. Begin your visit of the two-story outdoor mall with the Cultural Center and a stunning glass mural. The square features twelve bronze zodiac statues, each symbolizing unique characteristics.
- Type: Public space
- Why It’s a Gem: The interactive zodiac art in the open air is a must see and a unique photo spot!
- Address: 2100 S Archer Ave, Chicago
- Cost: Free
- Vibe: Mystical and artistic
7. The Magic Parlour
The Magic Parlour has many tricks up its sleeves! Witness unbelievable tricks and mind readings, 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.
- Type: Entertainment venue
- Why It’s a Gem: Experience an intimate professional magic show with engaging storytelling.
- Address: Palmer House Hilton, 50 W Randolph St, Chicago
- Cost: ~$93 per person (includes a complimentary drink from the bar)
- Vibe: Sophisticated and intimate
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.
- Type: Architectural landmark
- Why It’s a Gem: This whimsical photo spot sparks joy in kids and adults alike.
- Address: West Loop, 21 S Racine Ave, Chicago
- Cost: Free
- Vibe: Playful and creative
9. Challengers Comics + Conversation
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.
- Type: Retail & community space
- Why It’s a Gem: This comics store feels like home for long-time fans, seasoned collectors and newcomers to the hobby.
- Address: 1845 N Western Ave, Chicago
- Cost: Varies per item
- Vibe: Welcoming and enthusiastic
10. Twin Anchors
Twin Anchors was Frank Sinatra's favorite spot for a pre-concert meal in the Windy City, or so locals say! 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.
- Type: Restaurant (barbecue)
- Why It’s a Gem: This laid-back spot cooks up classic ribs and other barbecue favorites since 1932.
- Address: 1655 N Sedgwick St, Chicago
- Cost: $20–$30 per person
- Vibe: Cozy and nostalgic
11. Hoosier Mama Pie Company
Hoosier Mama Pie Company is recognized among a growing branch of Chicagoans as the best pie shop in the city. 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.
- Type: Bakery
- Why It’s a Gem: Find delicious scratch-made pies with creative flavors, perfect for anyone with a sweet tooth.
- Address: 1618 W Chicago Ave, Chicago
- Cost: $5 per slice / $20–$30 whole pie
- Vibe: Charming and homely
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 Chicago restaurants, each serving up dishes that are both innovative and undeniably delicious.
- Type: Culinary event
- Why It’s a Gem: Get a taste of many local spots in one outing and meet up with fellow foodies.
- Address: 1554 W Hollywood, Chicago
- Cost: $40–$75 per ticket
- Vibe: Festive and community-oriented
13. The Violet Hour
The Violet Hour, an award-winning bar, shies away from the attention it deserves. 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.
- Type: Cocktail bar
- Why It’s a Gem: Sip on artisanal drinks at this elegant hideaway fit for a monarch.
- Address: 1520 N Damen Ave, Chicago
- Cost: $10–$38 per cocktail
- Vibe: Sophisticated and intimate
14. Cindy's Rooftop
Cindy's Rooftop, perched on the Chicago Athletic Association, 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.
- Type: Rooftop bar & restaurant
- Why It’s a Gem: High up, the panoramic view of the park and the lake pairs wonderfully with dinner.
- Address: 12 S Michigan Ave, Chicago
- Cost: $20–$40 entrées / ~$18 cocktails
- Vibe: Lively and scenic
15. Thorne Miniature Rooms
Thorne Miniature Rooms, located inside the Art Institute of Chicago, were created by Narcissa Niblack Thorne and her team. Chicago architecture can touch the sky, but some designers have found the beauty in thinking small — miniature, in fact.
- Type: Museum exhibit
- Why It’s a Gem: Get up close with the delicate craftsmanship needed to bring these tiny rooms, full of historical detail, to life.
- Address: 111 S Michigan Ave, Chicago
- Cost: $32 general admission, free for children under 13
- Vibe: Educational and intriguing
16. Calumet Fisheries
For Calumet Fisheries, smoking fish is both a labor of love and 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.
- Type: Seafood shack
- Why It’s a Gem: Their legendary smoked fish, made in-house since 1948, is a must-try for locals and tourists.
- Address: 3259 E 95th St, Chicago
- Cost: $10–$20 per person
- Vibe: Casual and authentic
17. Margie's Candies
Margie's Candies has mountains of sugar-sweet ice cream, whipped cream clouds, and chocolate fudge rivers waiting for you. 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.
- Type: Ice cream parlor & candy shop
- Why It’s a Gem: In a curated vintage decor, the homemade sundaes will cool you down on warm summer days.
- Address: 1960 N Western Ave & Ravenswood, Chicago; 1813 W Montrose Ave. Chicago
- Cost: $10–$15
- Vibe: Nostalgic and family-friendly
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.
- Type: Urban legend/exploration site
- Why It’s a Gem: These underground tunnels are full of mystery, perfect for experienced urbex enthusiasts.
- Address: Various
- Cost: Free (unofficial)
- Vibe: Adventurous and mysterious
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.
- Type: Guided tours
- Why It’s a Gem: Learn the stories and view the architectural details of landmark hotels around Chicago.
- Neighborhood: The Loop
- Cost: Variable – See hotel website
- Vibe: Elegant and sophisticated
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.
- Type: Bar crawl/venue group
- Why It’s a Gem: Travel back in time in these secret-entrance bars that bring back the Prohibition flair of the past.
- Neighborhoods: River North & others
- Cost: $30–$50 per cocktail at upscale spots
- Vibe: Nostalgic meets modern
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. At our shows, the only thing you can expect is the unexpected. Book your tickets today and experience the spectacular performance for yourself.