12 Best Hidden Gems in Chicago: Discovering the city off the beaten path

by Jen
Hidden Gems in Chicago
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Looking for the best hidden gems in Chicago? Chicago’s most underrated attractions are outlined in this ultimate guide. Let’s explore Chicago off the beaten path.

Chicago, a city in Illinois, that effortlessly blends its rich history with modern marvels, where skyscrapers kiss the clouds and the shores of Lake Michigan beckon with a serene allure. While many are drawn to its iconic attractions like the towering Willis Tower or the gleaming Bean at Millennium Park, there’s a side to Chicago that remains untouched by the typical tourist’s gaze. Dive deeper, and you’ll uncover a treasure trove of hidden gems that showcase the city’s true spirit. From secret skyline viewpoints to local-approved eateries and art in unexpected places, Chicago is brimming with surprises waiting to be discovered. So, if you’re yearning to experience the Windy City in a way that few have, you’re in for a treat. Join us as we embark on a journey to uncover the Hidden Gems in Chicago that promise an adventure unlike any other.

The hidden gems in Chicago for all types of travelers
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Hidden Gems in Chicago

Eager to unearth the best hidden gems in Chicago? As highlighted before, this city is teeming with destinations away from the usual tourist trails, catering to every type of traveler. Dive deeper to reveal some of the most underrated places in Chicago.


Are you looking to explore beautiful art masterpieces? Or would you prefer a leisure stroll through tranquil landscapes? Whatever you’re planning, Chicago can accommodate your needs. Dive into this guide to discover the best hidden gems in Chicago.

1. Alfred Caldwell Lily Pool: A Tranquil Oasis in Lincoln Park

Nestled within the bustling Lincoln Park lies a serene haven that many Chicagoans hold dear – the Alfred Caldwell Lily Pool. This peaceful sanctuary, designed by landscape architect Alfred Caldwell, is reminiscent of a scene straight out of a Monet painting. Cascading waterfalls, meandering stone paths, and a plethora of native plants create a picturesque setting that’s perfect for a leisurely stroll or a moment of quiet reflection.

While the lily pool is undoubtedly beautiful throughout the year, it truly comes alive in spring. The water lilies bloom in a riot of colors, and the gentle hum of nature fills the air. It’s a place where you can momentarily escape the city’s hustle and bustle and immerse yourself in nature’s embrace.

For those pondering where to go in Chicago for a slice of nature amidst urban surroundings, the Alfred Caldwell Lily Pool is a must-visit. It stands as a testament to the city’s commitment to preserving pockets of greenery and offers visitors a chance to reconnect with nature.

Travel Tips:

Best Time to Visit: Spring and early summer when the lilies are in full bloom and the landscape is lush. Early mornings or late afternoons offer a peaceful experience

Proximity: Located in Lincoln Park, it’s a short walk from the Lincoln Park Zoo.

Duration: Spend 30 minutes to an hour to fully enjoy the tranquility and beauty of the pool

Cost: Entry is free

Alfred Caldwell Lily Pool in Lincoln Park is one of the hidden gems in Chicago.
Alfred Caldwell Lily Pool in Lincoln Park: A serene, Monet-like oasis with waterfalls and native plants.

For art enthusiasts and casual observers alike, the Wabash Arts Corridor in Chicago’s South Loop neighborhood is a visual treat. Often overlooked in favor of more traditional museums, this vibrant stretch is an ever-evolving canvas showcasing the city’s dynamic art scene. It’s one of the coolest places to go in Chicago if you’re keen on discovering contemporary art in an urban setting.

As you stroll through the streets, you’ll be greeted by massive murals, intricate installations, and thought-provoking pieces by both local and international artists. Each artwork tells a story, reflecting the city’s cultural diversity and the artists’ unique perspectives.

The best part? The Wabash Arts Corridor is constantly changing. New artworks pop up regularly, ensuring that there’s always something fresh to see. Whether you’re an art aficionado or just someone looking for Instagram-worthy spots, this open-air gallery is sure to captivate.

For those wondering what to do in Chicago that’s a bit off the conventional path, immersing oneself in the Wabash Arts Corridor’s artistic wonders is a delightful choice. It’s a testament to Chicago’s thriving arts culture and the city’s dedication to supporting creative expression.

Travel Tips:

Best Time to Visit: Daytime for the best visibility of murals

Proximity: Located in the South Loop

Duration: 1-2 hours

Cost: Free

The Wabash Arts Corridor in Chicago's South Loop neighborhood: A dynamic urban canvas for contemporary art.
The Wabash Arts Corridor in Chicago’s South Loop neighborhood: A dynamic urban canvas for contemporary art.

3. The Sky Chapel: A Spiritual Retreat Above the City

Perched 400 feet above the bustling streets of Chicago, the Sky Chapel offers a unique blend of spiritual solace and architectural brilliance. Located within the First United Methodist Church at the Chicago Temple Building, this hidden gem is the highest indoor worship space in the world.

As you ascend to the Sky Chapel, the city’s noise fades, replaced by a serene ambiance that invites introspection. The chapel’s stained-glass windows cast a kaleidoscope of colors, creating an ethereal atmosphere that’s perfect for meditation or quiet reflection.

But it’s not just the spiritual aspect that draws visitors. The Sky Chapel also offers panoramic views of Chicago’s iconic skyline. This makes it a beautiful destination in Chicago for both the soul and the eyes.

If you’re pondering where to go in Chicago for a spiritual retreat coupled with breathtaking views, the Sky Chapel is a must-visit. It’s a testament to the city’s architectural prowess and its commitment to preserving spaces of spiritual significance.

Travel Tips:

Best Time to Visit: Weekdays during the building’s open hours, as weekends might have private events or services

Proximity: Located in the heart of the Loop, it’s easily accessible by public transport, especially the ‘L’ trains

Duration: Plan for about 30 minutes to an hour to explore the chapel and take in the views

Cost: Entry is usually free, but donations to the church are appreciated

Sky Chapel in Chicago is a spiritual haven perched 400 feet above the city.
Sky Chapel in Chicago is a spiritual haven perched 400 feet above the city. | Source: https://www.choosechicago.com/

4. Navy Pier’s Secret Skyline View: A Panoramic Perspective

While Navy Pier is a well-known attraction in Chicago, not many are aware of the secret skyline view that awaits atop its parking garage. Bypass the usual crowds and head straight to the top floor, where a breathtaking panorama of the city unfolds before your eyes. It’s one of those hidden gems in Chicago that even some locals are yet to discover.

From this vantage point, the iconic Chicago skyline, with its mix of historic and modern architecture, stretches out in all its glory. The shimmering waters of Lake Michigan add to the spectacle, especially during sunset when the city is bathed in a golden hue.

For those wondering where to go in Chicago for an unobstructed and less crowded view of the city, this secret spot at Navy Pier is a fantastic choice. It’s a reminder that sometimes the best views are found in the most unexpected places.

Travel Tips:

Best Time to Visit: Sunset or nighttime for the best city views

Proximity: Located at the end of Navy Pier

Duration: 30 minutes to an hour

Cost: Free, but parking at Navy Pier has a fee

Navy Pier's parking garage hides a secret skyline view atop its top floor
Navy Pier’s parking garage hides a secret skyline view atop its top floor, offering a hidden gem in Chicago for those in the know.

5. The 606: Chicago’s Elevated Urban Oasis

Once an old rail line, The 606 has been transformed into a 2.7-mile elevated greenway that offers both residents and visitors a unique way to experience the city. It’s one of the most unique places to visit in Chicago, blending urban design with nature, art, and community engagement.

As you walk, jog, or bike along the trail, you’ll be treated to a mix of art installations, beautifully landscaped gardens, and observation points that offer glimpses of Chicago’s diverse neighborhoods. The 606 is more than just a park; it’s a living testament to Chicago’s commitment to sustainability and urban renewal.

For those pondering what to do in Chicago that offers a blend of nature, art, and urban exploration, The 606 is a top choice. It’s a reminder of the city’s innovative spirit and its dedication to creating spaces that foster community and well-being.

Travel Tips:

Best Time to Visit: Early mornings or late afternoons for fewer crowds

Proximity: Accessible from various points in the Logan Square, Humboldt Park, and West Town neighborhoods

Duration: 2-3 hours if you’re walking the entire trail

Cost: Free

The 606, a 2.7-mile elevated greenway, reimagines an old rail line into a unique urban-nature blend.
The 606, a 2.7-mile elevated greenway, reimagines an old rail line into a unique urban-nature blend.

6. Chicago River Kayaking: A Unique Waterway Adventure

While the Chicago Riverwalk is a popular spot for tourists and locals alike, there’s an even more thrilling way to experience the Chicago River: kayaking. Paddling along the river offers a fresh perspective of the city’s architectural marvels. This allows you to glide past iconic buildings and under historic bridges. It’s undoubtedly one of the best things to do in Chicago if you’re seeking a mix of adventure and sightseeing.

Companies like Wateriders offer guided kayak tours, ensuring a safe and informative journey. As you paddle, you’ll learn about Chicago’s rich history, its architectural wonders, and the significance of the river to the city’s development.

For those wondering where to go in Chicago for an active and immersive experience, Chicago River kayaking is a top pick. It’s a chance to see the Windy City from a vantage point few get to enjoy. This makes it a truly unique place to visit in Chicago.

Travel Tips:

Best Time to Visit: Late spring to early fall

Proximity: Multiple launch points along the river, including downtown

Duration: Tours typically last 2-3 hours

Cost: Varies based on tour operators

Kayaking on the Chicago River adds an adventurous twist to the city's iconic architectural sightseeing.
Kayaking on the Chicago River adds an adventurous twist to the city’s iconic architectural sightseeing.

7. Woolly Mammoth Antiques and Oddities: A Quirky Treasure Trove

For those with a penchant for the unusual, Woolly Mammoth Antiques and Oddities is a must-visit. Tucked away in the Andersonville neighborhood, this shop is a haven for collectors, artists, and anyone with a curious mind. It’s one of those unique places to visit in Chicago where every nook and cranny holds a surprise.

From vintage medical equipment and taxidermy to rare books and peculiar artifacts, the store’s eclectic inventory is a testament to the weird and wonderful. Each item has a story, and the friendly staff are more than happy to share tales of their origin and significance.

For those pondering beautiful places in Chicago with a twist, Woolly Mammoth Antiques and Oddities is a delightful detour from the usual tourist spots. It’s a reminder that Chicago is a city of contrasts, where history, art, and a touch of the bizarre come together in harmony.

Travel Tips:

Best Time to Visit: Weekdays for a quieter experience

Proximity: Located in the Andersonville neighborhood

Duration: 1-2 hours

Cost: Free entry, but items for purchase vary in price

Woolly Mammoth Antiques and Oddities in Andersonville is a haven for the curious, making it a unique place to explore in Chicago.
Woolly Mammoth Antiques and Oddities in Andersonville is a haven for the curious, making it a unique place to explore in Chicago.

8. The Secret Mermaid Sculpture: Oakwood Beach’s Mysterious Beauty

Tucked away at Oakwood Beach is a lesser-known piece of art that has intrigued locals and visitors alike: the Secret Mermaid Sculpture. This enchanting bronze statue, partially submerged in water, depicts a mermaid gazing wistfully towards the horizon. It’s one of those hidden gems in Chicago that combines natural beauty with artistic expression.

The sculpture’s origin remains a mystery, adding to its allure. Some say it’s the work of a local artist, while others believe it’s a tribute to the myths and legends of Lake Michigan. Regardless of its origins, the Secret Mermaid Sculpture offers a tranquil spot for contemplation and photography.

For those searching for beautiful destinations in Chicago that are off the beaten path, the Secret Mermaid Sculpture is a captivating find. It’s a testament to the city’s love for art and its ability to surprise even the most seasoned travelers.

Travel Tips:

Best Time to Visit: Sunrise or sunset for the best lighting

Proximity: Located at Oakwood Beach

Duration: 30 minutes to an hour

Cost: Free

The Secret Mermaid Sculpture at Oakwood Beach: A hidden gem in Chicago blending art and natural beauty.
The Secret Mermaid Sculpture at Oakwood Beach: A hidden gem in Chicago blending art and natural beauty.

9. Winter Garden at Harold Washington Library Center: An Urban Sanctuary

Amidst the hustle and bustle of Chicago’s downtown lies a serene escape that many overlook: the Winter Garden at the Harold Washington Library Center. Situated on the library’s top floor, this architectural marvel boasts a vast, airy atrium with a glass ceiling. This allows natural light to flood the space. It’s one of the coolest places to go in Chicago for a moment of calm.

Lush green plants, comfortable seating areas, and the gentle sound of water from the fountain create an oasis of tranquility. Whether you’re looking to read a book, work on your laptop, or simply relax, the Winter Garden offers a peaceful retreat from the city’s frenetic pace.

For those pondering beautiful places in Chicago that offer a blend of nature and architecture, the Winter Garden is a top choice. It’s a testament to Chicago’s commitment to creating public spaces that nourish the mind and soul.

Travel Tips:

Best Time to Visit: Weekdays during library hours

Proximity: Located in the Loop

Duration: 1-2 hours

Cost: Free

The Winter Garden is one of the hidden gems in Chicago.
The Winter Garden at the Harold Washington Library Center offers a peaceful escape with its airy atrium and natural light.

10. Charnel House: A Unique Venue for Avant-Garde Arts

Once a former funeral home, the Charnel House has been transformed into a unique venue that celebrates avant-garde arts and performances. Located in the Logan Square neighborhood, this space is a hub for experimental theater, music, dance, and visual arts. It’s one of the most unique places to visit in Chicago for those with a penchant for the unconventional.

The venue retains many of its original architectural features, adding to its atmospheric charm. High ceilings, stained glass windows, and a sense of history make every performance here a memorable experience. The Charnel House is not just a venue; it’s a testament to Chicago’s vibrant arts scene and its dedication to pushing boundaries.

For those wondering where to go in Chicago to experience the city’s edgier side, the Charnel House is a must-visit. It’s a reminder that Chicago is a city that embraces innovation and creativity in all its forms.

Travel Tips:

Best Time to Visit: Check their events calendar for performances

Proximity: Located in Logan Square

Duration: Duration varies based on the event

Cost: Ticket prices vary based on the event

The Charnel House in Logan Square: A former funeral home turned avant-garde arts hub.
The Charnel House in Logan Square: A former funeral home turned avant-garde arts hub.

11. Magic Parlour at Palmer House: An Evening of Enchantment

Step into a world of wonder and illusion at the Magic Parlour located within the historic Palmer House Hilton. Hosted by the renowned magician Dennis Watkins, this intimate show promises an evening of mind-bending magic, mentalism, and a touch of the theatrical. It’s one of those secret spots in Chicago where the line between reality and fantasy blurs.

Set in a luxurious, vintage-inspired parlor, guests are treated to a close-up magic experience like no other. Watkins’ masterful performances, combined with the venue’s opulent ambiance, make for a truly unforgettable evening.

For those pondering what to do in Chicago for a sophisticated and magical evening, the Magic Parlour is a top pick. It’s a testament to the city’s rich entertainment culture and its ability to offer experiences that captivate and mesmerize.

Travel Tips:

Best Time to Visit: Evening shows; reservations required

Proximity: Located within the Palmer House Hilton in the Loop

Duration: Approximately 90 minutes

Cost: Ticket prices vary

The Magic Parlour at the Palmer House Hilton: An intimate, mind-bending magic show that blurs the line between reality and fantasy.
The Magic Parlour at the Palmer House Hilton: An intimate, mind-bending magic show that blurs the line between reality and fantasy.

12. The International Museum of Surgical Science: A Journey Through Medical History

Housed in a grand historic mansion on Lake Shore Drive, the International Museum of Surgical Science offers a fascinating look into the world of medicine and its evolution over the centuries. It’s one of the unique places to visit in Chicago for those with a keen interest in science and history.

Spanning four floors, the museum boasts an extensive collection of medical artifacts, artworks, and exhibits. From ancient surgical instruments to interactive displays on modern medical techniques, there’s something to pique the curiosity of every visitor. The museum also pays tribute to pioneering figures in the field of medicine, celebrating their contributions and innovations.

For those pondering beautiful destinations in Chicago with an educational twist, the International Museum of Surgical Science is a must-visit. It’s a testament to the city’s commitment to preserving and showcasing knowledge, ensuring that the stories of medical pioneers live on for future generations.

Travel Tips:

Best Time to Visit: Weekdays for a quieter experience

Proximity: Located in the Gold Coast neighborhood

Duration: 2-3 hours

Cost: Admission fee with discounts for students and seniors

The International Museum of Surgical Science on Lake Shore Drive: A unique Chicago spot for history and science enthusiasts.
The International Museum of Surgical Science on Lake Shore Drive: A unique Chicago spot for history and science enthusiasts.

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.

Man walking with a bike along the sandy shoreline of North Avenue Beach in Chicago
Man walking with a bike along the sandy shoreline of North Avenue Beach in Chicago

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:

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. Scams: As with many tourist-heavy cities, be wary of street scams or people aggressively seeking donations for various causes.
  6. 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.
  7. 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.
  8. Taxes: Chicago has one of the highest sales taxes in the country, so be prepared for a slightly higher final price when making purchases.
  9. 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.

The hidden gems to visit in Chicago right now
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