Secret Spots and Not-to-be-Missed Hidden Gems in Chicago

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The Windy City is well known for its world-class architecture and museums, its diverse neighborhoods and the majestic Lake Michigan skyline. From dazzling public art to an historic place to hear live music, here are the hidden gems in Chicago locals know and visitors love.

Chicago is known for its gangster history (think Al Capone), skyscrapers like Willis Tower (which locals still call Sears Tower) and the world-renown Art Institute of Chicago. And, of course, there is the food. Chicagoans love their Italian cuisine, deep dish pizza and Chicago-style hot dogs.

Even the city’s nickname is a hidden gem. While most people think it refers to the winds that blow in from Lake Michigan cooling the city in the summer and freezing it in the winter, that’s not why it’s called the Windy City. It got that nickname back in 1893 when Chicago was competing with New York City to host the 1893 World’s Fair. An NYC editorial writer referred to the “windbags” from the Midwest. Chicago won the fair and the nickname stuck.

Now that you know that hidden history, check out these secret spots and hidden gems in Chicago.

SheBuysTravel Tip: It can be expensive to take a regular taxi around downtown Chicago. A more affordable, fun and scenic way is to travel by water taxi along the Chicago River. 

See Chicago’s Skyline

Chicago is known for its unique architecture and more than 1,300 skyscrapers. You’ll get amazing views of the skyline from the Skydeck at the 1,450-foot tall Willis Tower.

But for a less touristy experience, head to Navy Pier. Take the elevator to the top floor of the garage parking structure for expansive city views.

Or, see the skyscrapers from the river. The best known option is the famed Chicago River Architecture Tour. Or do it the secret way: by kayak. Several outfitters rent kayaks and offer guided tours of the river.

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Garden of the Phoenix

Located on Wooded Island in Jackson Park, the serene Garden of the Phoenix is one of Chicago’s hidden gems.

The azalea-studded Japanese garden features a waterfall and foot bridges. A gravel path meanders through Japanese maples, green spaces and pines.

Find the garden just south of the Museum of Science and Industry, one of the best science museums in the country.

Rack of Divvy bikes in Chicago, a super way to explore the hidden gems
Rent a bike to explore Chicago’s Lakefront Trail. Photo courtesy: Pixabay

Biking on the Chicago Lakefront Trail

Biking is an excellent way to see the sights of the city. The Lakefront Trail is a flat, 18-mile paved path that follows the Lake Michigan shoreline. Bike rentals provide everything you need for a family bike ride. Chicago’s bike rental program, called Divvy, is a fun, affordable way to get around.

A bike tour is another option. It’s a great way to see the city, enjoy lake views and not worry about getting lost. Tours take you through neighborhoods, the lakefront, The Loop (another name for Downtown Chicago), Lincoln Park and more.

Sights to see along the way

Take time for sightseeing as you cruise along the bike path. Watch the beach volleyball players at North Avenue beach and visit Lincoln Park Zoo, one of the last free zoos in the country. Don’t leave before walking through the Lincoln Park Conservatory next door to the zoo. It’s also free to visit.

Plus, you’ll also peddle past iconic downtown sites like Buckingham Fountain, Navy Pier and Adler Planetarium. If you have more time, you’ll also have a chance to visit museums, such as the Field Museum, the Shedd Aquarium and Soldier Field.

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Grand main hall staircase at the Driehaus Museum, one of Chicago's hidden gems
The Main Hall at the Driehaus Museum. Photo credit: Steve Hall of Hedrich Blessing

The Driehaus Museum

Travel back to America’s Gilded Age (1870s to early 1900s) at The Driehaus Museum. Formerly the home of banker Samuel Mayo Nickerson, it was turned into a museum by philanthropist Richard H. Driehaus in 2003. He preserved and refurbished the mansion (dubbed The Marble Palace), which is an architectural gem.

When you visit, you’ll enter the museum through the same door guests of the Nickersons used in the late 19th century. All of the rooms are grand and offer a peek into Chicago’s history.

Garfield Park Conservatory

The 184-acre Garfield Park Conservatory is free and has a lot to offer families. Stroll along meandering trails with massive, glass dome greenhouses filled with unique tropical plants, cacti and flowers. In addition, there’s a children’s play garden that encourages climbing.

Take the Green Line L train just a few stops west of downtown to the Conservatory stop. From there, it’s just a few steps from the front door of the Conservatory.

Although the park is free, donations are appreciated.

Ping Tom Memorial Park

Discover under-the-radar skyline views at the Ping Tom Memorial Park in Chinatown.

Formerly an abandoned rail yard, the waterfront park is a scenic green space ideal for strolls, picnics and even kayaking. Summer events feature concerts and a Dragon Boat race. Don’t leave before having lunch or dinner at one of the Chinese restaurants that line the streets of Chinatown.

SheBuysTravel Tip: Chinatown is easily reached by L train. You can also catch the water taxi from the park. The seasonal boat travels between Ping Tom Park from the Loop, making it an easy and scenic way to get to Chinatown.

Admire Public Art

After perusing The Art Institute of Chicago, get off the beaten path to find public art all around the Loop and on the walls and in alleys of the neighborhoods.

The Wabash Arts Corridor in the Loop is one of the most expansive public arts programs in the country. It features murals, installations and, in the evenings, Art on the Mart. That is a series of projections that use the  Merchandise Mart as the screen. The Mart, a building so big that it once had its own ZIP code, is located at Wells Street and the Chicago River. Find a spot on the south side of the river along Wacker Drive for the best views.

aerial view of Lurie Garden one of the hidden gems in Chicago's Millennium Park
Lurie Garden is among secret spots in Millennium Park. Photo courtesy: Pixabay

The Lurie Garden

Millennium Park is best known for The Bean, the iconic sculpture that invites selfies. But the park is also home to a secret garden – the 2.5-acre Lurie Garden. The garden’s design celebrates Chicago’s motto, “Urbs in Horto,” Latin for “City in a Garden.”

The four-season urban oasis is living art that represents Chicago’s unique culture, ecology, history and people. Plus, it’s home to a wide variety of plants, animals and insects.

Oak Street Beach

Michigan Avenue and Oak Street are Chicago’s high end shopping strips. Escape the hustle and bustle on days when the  weather is nice. Just walk a few blocks north on Michigan Avenue and through the underpass to get to Oak Street Beach. It’s a free public sand beach with a stunning skyline backdrop.

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Celebrate Latin Culture

The National Museum of Mexican Art in Pilsen is home to one of the largest Mexican art collections in the US. It’s free and easily reachable via the Pink Line L train.

While you’re in Pilsen, spend some time wandering around the charming neighborhood to see the Instagrammable street art and stop at a mom and pop shop for lunch.

Visit Graceland Cemetery and Arboretum

Graceland Cemetery is one of Chicago’s finest and unique hidden treasures. Established in 1860, it’s located in the North Side community area of Uptown.

The cemetery is the final resting place for many prominent Chicago athletes, politicians, industrialists and architects. But it’s open to the public to enjoy the architecture and lush gardens.

Enjoy Live Music

The aptly named Hideout is a dive bar that is not only a hidden gem but a historic one as well. It opened in 1934 as a hideout for those seeking creative freedom and artistic rebellion. It’s a place where you can let your hair down, and enjoy live music featuring alternative styles.

The Hideout hosts various events to support many local causes. Find the Hideout in the center of the industrial corridor along the North Branch of the Chicago River.

Native Angeleno and seasoned travel journalist Mimi Slawoff writes for numerous print and digital publications. She is also the author of Oldest Los Angeles (Reedy Press, 2022). A lifelong world traveler, Mimi is an award-winning journalist who writes about outdoor adventures, cruises, Europe and cultural activities. Mimi has three grown kids and lives with her husband and their dog, Maya, in Los Angeles.
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