Chicago floored me in ways I never expected. Everyone talks about The Bean and deep-dish pizza, but when I ventured into neighborhoods like Logan Square with its tree-lined boulevards and incredible food scene or Pilsen with its vibrant murals and authentic taquerias, I discovered a Chicago that pulses with life beyond the gleaming downtown towers.
From the architectural wonders scattered throughout Ravenswood to the stunning lakefront parks that actually let you breathe, Chicago contains some of the best places in Illinois for food fanatics and culture vultures alike. After four visits spanning brutal winters and perfect summer weekends, I’ve finally compiled this list of 12 incredible spots that deserve your attention more than another selfie at Willis Tower or waiting in line for touristy pizza you’ll regret an hour later.
Best Things to Do in Chicago
Looking to explore hidden gems in Chicago? From the vibrant culture of Pilsen to the serene beauty of Promontory Point, Chicago is packed with hidden treasures.
Stroll through the historic charm of Pullman District, marvel at the unique art in Garfield Park Conservatory, or explore the lively atmosphere of Andersonville. Whether you’re into art, history, or local flavor, here are 12 of Chicago’s most breathtaking hidden gems!
1. Alfred Caldwell Lily Pool
Ready to discover Chicago’s most peaceful secret garden hidden in plain sight?
Tucked behind a modest entrance in Lincoln Park, the Alfred Caldwell Lily Pool reveals itself as a prairie-style masterpiece where cascading water flows over stratified stonework. The meticulously restored 1940s landscape creates perfect moments for contemplation without the crowds of nearby attractions.
What makes this spot magical is how it transforms seasonally—spring brings vibrant lily blooms while fall offers stunning foliage against the pavilion’s architectural lines. I found myself completely forgetting I was in the middle of a bustling city.
Located at the eastern edge of Lincoln Park near Fullerton Avenue, it’s easily accessible yet mysteriously overlooked by most visitors. The free entry makes it perfect for a quick morning visit before heading to nearby North Avenue Beach or Lincoln Park Zoo.
Pro tip: Arrive early on weekdays to experience the space in near solitude.
2. Wabash Arts Corridor
Want to experience a constantly evolving outdoor art museum that towers eight stories above city streets?
The Wabash Arts Corridor transforms mundane building facades into massive canvases spanning eight city blocks in the South Loop. Massive murals from international and local artists create a visual feast that changes regularly, ensuring no two visits are ever quite the same.
Between Columbia College buildings and historic structures, you’ll discover stunning large-scale works that tackle everything from social justice to pure visual delight. The contrast of contemporary art against Chicago’s architecture creates a uniquely photogenic landscape.
Located primarily along Wabash Avenue between Roosevelt and Van Buren, this walkable district sits near Grant Park and the Art Institute. Grab a coffee from Hero Coffee Bar on Wabash to fuel your exploration.
I prefer starting at Roosevelt and working north, capturing the changing neighborhood vibe.
3. The Sky Chapel
Ever prayed or meditated 29 floors above Chicago’s bustling streets?
Perched atop the Chicago Temple Building, the hidden Sky Chapel offers spiritual sanctuary within the world’s tallest church building. This intimate space features jewel-toned stained glass, hand-carved wooden pews, and panoramic views through Gothic-inspired windows.
The juxtaposition of sacred quietude against the urban landscape creates a uniquely Chicago moment of zen. Finding this gem requires insider knowledge—enter at 77 W. Washington Street across from Daley Plaza, take the elevator to floor 23, then follow signs to the second elevator.
Visits require a quick call ahead to the church office, but the effort rewards you with both architectural splendor and a peaceful respite from Michigan Avenue shopping. I was amazed at how few locals even know this place exists.
The chapel’s hushed atmosphere provides the perfect reset during a day of urban adventure.
4. Navy Pier’s Secret Skyline View
Tired of paying $30 for observation deck views alongside hundreds of tourists?
Chicago’s most spectacular skyline panorama awaits at the eastern edge of Navy Pier, completely free and often blissfully empty of crowds. This hidden viewpoint offers breathtaking vistas without the ticket prices of observation decks.
The secret spot sits at the pier’s far end past all the attractions—just continue walking until you reach the small lighthouse structure. From there, you’ll capture the entire downtown skyline, Lake Michigan’s vastness, and the architectural marvel of the city meeting water.
Located about a 15-minute walk from the pier’s entrance, this viewpoint provides perfect photo opportunities at sunrise and sunset. Nearby, Offshore Rooftop offers crafted cocktails with similar views if you prefer sitting with drinks.
I stumbled upon this spot during an early morning run and couldn’t believe more photographers weren’t there.
5. The 606
Looking for the perfect way to explore four of Chicago’s coolest neighborhoods in one scenic adventure?
Chicago’s answer to New York’s High Line, The 606, transforms an abandoned railway into an elevated urban trail stretching 2.7 miles through the city’s hippest enclaves. Unlike its more famous counterpart, this path feels authentically local rather than tourist-oriented.
The pathway connects Wicker Park, Bucktown, Humboldt Park, and Logan Square, offering both a scenic route and a practical way to explore these vibrant districts. Passing through residential areas and past small art installations, you’ll glimpse authentic Chicago life rarely seen on standard tours.
Access points dot the trail approximately every quarter-mile, with the eastern entrance near Walsh Park (1722 N. Ashland) offering a convenient starting point. Grab breakfast at nearby Mindy’s Hot Chocolate before your urban hike.
I’ve found sunset visits especially rewarding when the path lights create a magical ambiance.
6. Chicago River Kayaking
Ever wanted to paddle directly beneath towering skyscrapers while seeing Chicago from a completely new angle?
Experience the architectural canyon of downtown from water level by kayaking the Chicago River—a perspective that transforms familiar landmarks into awe-inspiring vertical monuments. This active adventure offers both exercise and unmatched photo opportunities.
Several outfitters including Wateriders and Urban Kayaks, offer guided tours or rentals for independent explorers. The twilight tours reveal the magic of the city’s lights reflecting off skyscrapers and rippling water.
Launch points exist at multiple locations, with the Riverwalk near Michigan Avenue providing the most convenient downtown access. Most tours last 1-2 hours, making this activity easy to fit into a packed itinerary.
I’ve never felt smaller or more amazed by Chicago’s architectural might than while paddling beneath its massive bridges with skyscrapers towering hundreds of feet overhead.
7. Woolly Mammoth Antiques and Oddities
Ready to browse Victorian medical devices, vintage taxidermy, and crystallized bat skeletons?
Woolly Mammoth in Andersonville houses Chicago’s most delightfully macabre collection of curiosities and conversation pieces. This modern-day cabinet of wonders defies easy categorization—vintage medical instruments share space with articulated skeletons and preserved specimens.
The carefully curated collection walks the line between creepy and captivating. Each visit reveals new treasures as inventory constantly evolves with one-of-a-kind items you won’t find anywhere else.
Located at 1513 W. Foster Avenue in the charming Andersonville neighborhood, the shop makes a perfect detour while exploring the area’s Scandinavian heritage. Nearby Simon’s Tavern offers the perfect spot to discuss your strange discoveries.
I spent an hour completely mesmerized by the artful arrangements and unusual finds. While not for the squeamish, the shop offers genuinely unique souvenirs that will spark more dinner party conversations than anything on Michigan Avenue.
8. The Secret Mermaid Sculpture
How many thousands of tourists cross Michigan Avenue Bridge each day with no idea about the whimsical secret beneath their feet?
Hidden under the bridge’s massive structure, the Man with Fish sculpture (nicknamed “the mermaid” by locals) sits tucked away at river level. Created by renowned artist Henry Hering in 1940, this bronze figure wrestling an enormous fish pays tribute to Chicago’s maritime heritage.
It’s semi-hidden placement creates a delightful urban treasure hunt for curious explorers. To find this gem, descend to the Riverwalk near the McCormick Bridgehouse & Chicago River Museum, then look for the figure on the bridge’s underside.
The sculpture provides a perfect excuse to explore the revitalized Riverwalk’s cafes and wine bars. I love watching visitors’ faces light up when they first spot this hidden artwork.
The location offers a unique vantage point for admiring the bridge’s mechanical workings and watching tour boats pass.
9. Winter Garden at Harold Washington Library Center
Did you know Chicago’s most spectacular glass-domed conservatory hides on the top floor of a public library?
The Winter Garden at Harold Washington Library surprises visitors with its magnificent vaulted ceiling, hanging gardens, and stunning architectural details. This light-filled atrium on the 9th floor feels worlds away from the bustling South Loop below.
Ornate cast iron, abundant natural light, and comfortable seating create an ideal spot for reading or simply appreciating the soaring space. The intricate glass dome draws the eye upward while potted plants and trees create a peaceful atmosphere.
Located at 400 S. State Street, the library sits conveniently near multiple transit options. The garden remains open during regular library hours, making it an excellent retreat during inclement weather.
I noticed how few tourists had discovered this free architectural marvel—despite it being just blocks from major attractions. It’s perfect for recharging before continuing your urban adventure.
10. Charnel House
How many performance venues can claim they once prepared bodies for burial?
Theatrical adventures in unexpected places define Chicago’s vibrant arts scene, and The Charnel House epitomizes this spirit. This former funeral home transformed into an avant-garde theater space in Bucktown offers performances that border on immersive art installations.
The historic 1904 building retains hints of its macabre past while housing cutting-edge theater, film screenings, and art events. The unusual setting creates productions where the space itself becomes part of the performance.
Located at 3421 W. Fullerton Avenue, the venue sits in Logan Square’s arts district, surrounded by independent galleries and innovative restaurants. Grab dinner at a nearby Lula Cafe before a show for a perfect cultural evening.
I was captivated by how the building’s history influences each production. Check their calendar when planning your trip—performances often sell out due to the intimate venue size.
11. Magic Parlour at Palmer House
Ever watched a master magician perform impossible illusions from three feet away while sipping fine whiskey in a historic hotel?
The Magic Parlour creates an intimate evening of astonishment hosted in the legendary Palmer House Hotel. This sophisticated experience features magician Dennis Watkins performing close-up illusions for just 44 guests per show.
The elegant third-floor venue with vintage furnishings creates the perfect atmosphere for sophisticated deception. Unlike large-scale illusion shows, this intimate performance puts you close enough to scrutinize every move—yet the magic remains inexplicable.
Located within one of Chicago’s most historic hotels at 17 E. Monroe Street, the venue sits conveniently in the Loop near theaters and fine dining. The show includes a complimentary glass of wine, enhancing the parlor party atmosphere.
I found myself repeatedly glancing at other guests’ faces to confirm they were equally baffled by what we’d just witnessed.
12. The International Museum of Surgical Science
Want to explore four floors of medical curiosities inside a magnificent 1917 lakefront mansion?
Medical history meets macabre fascination at the International Museum of Surgical Science in Gold Coast. This unusual collection spans four floors of surgical artifacts, anatomical art, and medical innovations that simultaneously educate and unsettle.
From ancient trepanation tools to iron lungs, the exhibits provide fascinating glimpses into medicine’s evolution. The building itself—a limestone mansion with ornate details—adds to the slightly eerie experience of examining centuries of surgical history.
Located at 1524 N. Lake Shore Drive with stunning Lake Michigan views, the museum offers a thought-provoking alternative to typical cultural institutions. Nearby Oak Street Beach provides a cheerful counterpoint for after your visit.
I found myself unexpectedly captivated by the early anesthesia devices and anatomical wax models. This hidden gem delivers both historical insight and conversation-starting oddities worth the detour from Michigan Avenue.
Frequently asked questions about the best hidden gems in Chicago
Are you searching for more content about where to go in Chicago? Here are some common questions (and answers) I get asked a lot about the most underrated places in Chicago.
What is one thing Chicago is known for?
Chicago is renowned for its iconic skyline, rich history, and deep-dish pizza. It’s a city that beautifully blends architectural marvels with a vibrant arts and culture scene.
What is Chicago’s best kept secret?
While Chicago boasts many popular attractions, its best kept secret lies in the numerous hidden gems scattered throughout the city. From secluded spots like the Secret Mermaid Sculpture at Oakwood Beach to quirky venues like the Charnel House, there’s always something unexpected to discover.
Where are some hidden gems in Chicago for nature lovers?
The 606 is a transformed rail line that offers a unique blend of nature and urban design. Another gem is the Winter Garden at Harold Washington Library Center, an urban oasis with lush greenery and a tranquil ambiance.
How do I find out about hidden gems in Chicago?
One of the best ways to discover hidden gems in Chicago is by exploring local blogs, joining city-specific forums, or engaging with Chicagoans on social media platforms. Additionally, taking guided tours with a local focus or simply wandering the city’s diverse neighborhoods can lead you to lesser-known spots. This article also highlights several unique and off-the-beaten-path destinations that are worth a visit in the Windy City.
How can I experience the coolest places to go in Chicago?
To truly experience the city’s charm, venture to places like Woolly Mammoth Antiques and Oddities for a quirky shopping experience or kayak along the Chicago River for a unique waterway adventure.
How can I experience Chicago’s history in a unique way?
The International Museum of Surgical Science offers a deep dive into medical history within a grand historic mansion. From ancient surgical instruments to interactive displays on modern techniques, it’s a journey through time in a unique setting in Chicago.
What to beware of in Chicago?
While Chicago is a vibrant and culturally rich city, like any major urban area, there are certain things visitors should be aware of for a safe and enjoyable experience:
- Crime in Certain Areas: Some neighborhoods, particularly on the city’s South and West sides, have higher crime rates. It’s always a good idea to research neighborhoods before visiting and to stay aware of your surroundings.
- Weather: Chicago’s weather can be unpredictable. Winters can be bitterly cold with heavy snowfall, while summers can be hot and humid. It’s often called the “Windy City”, so be prepared for gusty conditions year-round.
- Traffic: Chicago’s traffic can be dense, especially during rush hours. If you’re driving, be prepared for potential delays. Also, be cautious of cyclists; the city has many bike lanes.
- Parking: Parking in downtown Chicago can be expensive and hard to find. Consider using public transportation, rideshares, or parking outside the city center and taking the train in.
- Scams: As with many tourist-heavy cities, be wary of street scams or people aggressively seeking donations for various causes.
- Public Transportation at Night: While the ‘L’ train system is generally safe, some lines and stations can be less so late at night. Always stay alert and aware of your surroundings.
- Lake Michigan’s Currents: The lake’s beaches are beautiful, but the water can have strong undertows and rip currents. Always heed warning flags and signs.
- Taxes: Chicago has one of the highest sales taxes in the country, so be prepared for a slightly higher final price when making purchases.
- Events and Festivals: While they are a lot of fun, large events can also mean crowded public transportation, higher hotel prices, and booked restaurants.
What is a hidden gem of Illinois?
One of the hidden gems of Illinois is the Starved Rock State Park. Located in the Illinois River Valley, this park is a stark contrast to the flat landscapes often associated with the state.
Starved Rock State Park boasts a series of canyons and waterfalls, shaped by glacial meltwater thousands of years ago. The park has over 13 miles of trails that lead to these waterfalls, especially after a rain or during the spring thaw. The sandstone bluffs rise over 125 feet above the river, offering breathtaking views, particularly during autumn when the foliage turns vibrant shades of red, orange, and yellow.
In addition to its natural beauty, the park has a rich history. Its name, “Starved Rock,” comes from a Native American legend of a band of Illiniwek who died of starvation atop the 125-foot sandstone butte.
The park also offers a variety of activities year-round, from fishing and boating in the summer to ice climbing in the winter. The Starved Rock Lodge, built by the Civilian Conservation Corps in the 1930s, provides accommodations and is listed on the National Register of Historic Places.
While it’s one of the most popular state parks in Illinois, many outside the Midwest remain unaware of this stunning natural sanctuary, making it a true hidden gem.
Final thoughts on Chicago’s hidden gems
Chicago, with its iconic skyline, deep-dish pizza, and vibrant arts scene, is a city that never ceases to amaze. But beyond the well-trodden paths of Millennium Park and the Magnificent Mile lies a treasure trove of hidden gems waiting to be discovered. From serene urban oases to quirky shops and avant-garde performance spaces, the Windy City offers a plethora of unique experiences that often fly under the radar.
Whether you’re a long-time resident looking to rediscover the city or a first-time visitor eager to explore beyond the usual tourist spots, these hidden gems, including where to stay in Chicago, offer a fresh perspective on what makes Chicago truly special. So, the next time you find yourself wandering the streets of this magnificent metropolis, remember that there’s always something new and unexpected waiting just around the corner. Dive in, explore, and let Chicago’s lesser-known wonders captivate your heart and imagination.
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