11 Unexpected Things to Do in Chicago for a Fresh Take on the Windy City

Chicago offers way more than just deep-dish pizza and the Bean. Beyond the typical tourist attractions, the Windy City hides amazing experiences most visitors never discover. Whether you’re a local looking for something new or a traveler wanting to see the authentic Chicago, these unexpected activities will show you a completely different side of the city. Get ready to explore hidden gardens, secret theaters, and cultural treasures that showcase Chicago’s true character.

1. The Magic Parlour

Tucked away in the historic Palmer House Hotel lies a mesmerizing experience that transports you to the golden age of illusion.

Master magician Dennis Watkins performs mind-boggling tricks in an intimate 40-seat venue where everyone gets a front-row experience. The show blends sophisticated sleight-of-hand with heartfelt storytelling, creating moments of genuine wonder rather than just spectacle. Many guests report their jaws literally dropping during performances.

Unlike large-scale magic shows, this cozy parlour setting means you’re never more than a few feet from the impossible happening right before your eyes. Perfect for date nights or making ordinary evenings extraordinary!

2. The 606 Trail

Formerly an abandoned railway line, this 2.7-mile elevated path has transformed into Chicago’s answer to New York’s High Line. Connecting four diverse neighborhoods—Wicker Park, Bucktown, Humboldt Park, and Logan Square—the trail offers a peaceful escape above bustling city streets.

Local artists have turned the path into an open-air gallery with rotating installations that change with the seasons. Pause at one of the many lookout points for spectacular downtown skyline views you won’t find in guidebooks.

Morning joggers, afternoon cyclists, and sunset strollers share this urban oasis. Stop at the many access points to explore unique shops and eateries in neighborhoods tourists rarely visit.

3. International Museum of Surgical Science

Housed in a stunning lakefront mansion, this unusual museum offers a fascinating—sometimes spine-tingling—journey through medical history. Ancient trepanation tools, iron lungs, and early X-ray machines tell the story of how far medicine has come.

The museum’s marble halls contain over 10,000 artifacts including Japanese surgical scrolls, primitive amputation saws, and a collection of heart valves that trace the evolution of cardiac surgery. Each room explores different medical specialties with exhibits that are equal parts educational and eerie.

Don’t miss the beautiful anatomical paintings and sculptures that blend art with science. The museum stands as America’s only institution dedicated exclusively to surgical history and practices.

4. Chicago Greeter Tour

Skip the cookie-cutter tourist experiences and explore Chicago through a local’s eyes. This free program pairs visitors with passionate Chicago residents who customize walking tours based on your interests—whether that’s architecture, food, music, or neighborhood culture.

Your volunteer guide might show you their favorite hidden bookstore, the best spot for authentic Polish pierogi, or a community garden tucked between historic buildings. These aren’t professional tour guides but enthusiastic locals sharing their personal version of Chicago.

Tours venture into neighborhoods rarely seen by tourists, offering authentic glimpses into Chicago’s diverse communities. Advance registration is required, but the personalized experience offers insights no guidebook could provide.

5. The Violet Hour

Behind an unmarked door covered in ever-changing murals lies one of Chicago’s most sophisticated drinking experiences.

This speakeasy-style cocktail lounge enforces strict house rules—no cell phones, no standing at the bar—creating an atmosphere of refined relaxation rare in today’s world. Mixologists craft drinks with scientific precision, often using house-made ingredients and unexpected flavor combinations. The high-backed chairs and dim lighting create intimate conversation spaces, while the carefully curated music never overwhelms.

Arrive early as lines form quickly, and remember there’s no sign—look for the doorway with the distinctive mural in Wicker Park. The seasonal menu changes frequently, encouraging regular visits to sample their latest liquid creations.

6. The Charnel House

A former funeral home transformed into an experimental performance space, The Charnel House offers theatrical experiences unlike anything in Chicago’s mainstream venues. The black box theater hosts boundary-pushing plays, immersive shows, and avant-garde performances that engage audiences in unexpected ways.

The building’s history adds an atmospheric backdrop to productions, with original architectural details preserved throughout the space. Shows often incorporate the unique layout, with performances sometimes moving through different rooms for a truly immersive experience.

Beyond theater, the venue hosts film screenings, live music, and multidisciplinary arts events. Check their calendar for upcoming performances—each visit promises something completely different from traditional Chicago entertainment options.

7. Alfred Caldwell Lily Pool

Hidden within Lincoln Park lies a prairie-style masterpiece designed in 1936 by landscape architect Alfred Caldwell. This secluded garden showcases native plants surrounding a lily pond, with stratified limestone pathways leading visitors through a meticulously designed natural sanctuary.

The pavilion’s horizontal lines and natural materials reflect the Prairie School of architecture championed by Frank Lloyd Wright. Water trickles gently over stepping stones, creating a peaceful soundtrack that makes the city noise fade away completely.

Spring brings vibrant wildflowers while autumn transforms the space with golden hues. Birdwatchers flock here to spot migratory species making their seasonal stops. This National Historic Landmark remains one of Chicago’s most perfectly preserved yet least-known architectural treasures.

8. Garfield Park Conservatory

Often overshadowed by its Lincoln Park counterpart, this botanical wonderland houses one of the largest greenhouse collections in America. Eight indoor display gardens transport visitors from Chicago’s concrete jungle to lush tropical rainforests, ancient fern forests, and desert landscapes.

The Fern Room features a breathtaking indoor lagoon designed to resemble what Illinois might have looked like millions of years ago. Massive palms reach toward the soaring glass ceilings while seasonal flower shows transform the space throughout the year. Outside, 10 acres of outdoor gardens showcase urban agriculture initiatives and community green spaces.

Free admission makes this an accessible escape year-round—especially valuable during Chicago’s notorious winters when the warm, humid air offers a perfect tropical retreat.

9. 16th Street Murals

Along a mile-long stretch in Pilsen, over 150 vibrant murals transform ordinary walls into extraordinary canvases. Local and international artists have created this open-air gallery celebrating Chicago’s Mexican-American heritage and addressing social justice themes with bold colors and powerful imagery. Each mural tells a different story—from historical events to contemporary social commentary.

The constantly evolving collection means repeat visits always reveal new artistic discoveries along the concrete canvas. Unlike formal museums, this grassroots art space encourages photography and creates perfect backdrops for memorable pictures.

The surrounding neighborhood offers authentic Mexican restaurants where you can refuel after your art walk. Visit during the annual Pilsen Open Studios event to meet artists creating new works in real-time.

10. Rooftop Cinema Club

Movie nights reach new heights at this elevated outdoor theater experience. Perched atop Chicago buildings, these screenings pair classic and contemporary films with spectacular skyline views that create a magical backdrop as the sun sets.

Unlike standard theaters, guests relax in comfortable deck chairs with wireless headphones that deliver perfect sound while blocking city noise. The experience begins before the film, with themed cocktails and games creating a festive atmosphere as day turns to night. From cult classics to recent releases, the carefully curated film selection appeals to various tastes.

Blankets are provided on cooler evenings, making this a three-season attraction. Advance tickets are essential as screenings regularly sell out, especially for popular films and perfect weather nights.

11. National Museum of Mexican Art

Tucked away in the vibrant Pilsen neighborhood, this cultural gem houses the largest collection of Mexican art in the United States. Unlike larger downtown museums, this free institution offers an intimate look at both traditional and contemporary works spanning 3,000 years of Mexican culture.

The museum’s Day of the Dead exhibition ranks among the most comprehensive outside Mexico, featuring elaborate ofrendas (altars) and artistic interpretations of this important celebration.

Rotating galleries showcase everything from pre-Columbian artifacts to cutting-edge works by emerging Mexican and Mexican-American artists. Beyond visual arts, the museum hosts traditional music performances, film screenings, and cultural workshops. The gift shop offers authentic crafts supporting artisans from both sides of the border.