Hidden Gems in Chicago: How To Get off the Beaten Path

Black Chicagoans, such as Daniel Hale Williams, Mahalia Jackson, and Oprah Winfrey, have innovated everything from heart surgery and gospel music to daytime talk shows. Concentrated on the city’s South Side, historically Black neighborhoods including Bronzeville, Pullman, and Hyde Park (home to the Obamas’ stately residence), feature a wealth of museums and informative historical landmarks. Start exploring by sampling Chicago's favorite fried chicken at Harold’s or book a city tour to find other hidden treasures on Chicago’s South Side.

Not far from the Loop, the former working-class neighborhood of Old Town is now one of the city’s wealthiest. Here, you can discover landmarks such as the Buddhist temple, founded by resettled Japanese-Americans during World War II, and the home of Henry Geber, the activist who founded the country’s first documented LGBTQ+ advocacy organization.

You can also learn about Old Town's 19th-century cottage architecture on a guided walking tour, and stop for ribs at Twin Anchors Restaurant & Tavern, a Frank Sinatra favorite.

Did you know?: Old Town is home to Second City, the improv theater that trained comedians such as Tina Fey, Amy Poehler, and Steve Carrell.

Groundbreaking architecture isn’t only found in the Chicago Loop. The Wicker Park neighborhood teems with Victorian-era architecture and unique things to do in Chicago. Start with a stroll down Milwaukee Avenue and surrounding streets to shop in a former bank vault, gawk at quirky sculptures such as Jerzy S. Kenar’s Shit Fountain, and browse comics by local artists. Beyond the commercial zones, you can meander residential streets lined with 19th-century mansions and modest historical homes that once housed artists such as the writer Nelson Algren. Take a walking tour of the side streets to spot mansions and other secret places in Chicago while admiring the city architecture.

The Loop may be a well-worn stop on the Chicago tourist trail, but there’s one part—or layer, rather—that isn’t. One of the best alternative Chicago attractions is the city’s extensive underground tunnel system, dubbed the Chicago Pedway. It's a complex system linking more than 40 city blocks and 50 Chicago buildings. Each day, tens of thousands of commuters pass through the restaurants, shops, and hidden treasures, such as hard-to-find stained glass windows, in this city under the city. Don’t rely on GPS, or even the signage—a guided tour is a must.

Get off the beaten path in Chicago in Pilsen, the historical heart of Chicago’s Mexican-American community, and explore the neighborhood’s extensive network of 16 Street Murals on a private sightseeing tour. Originating as protest art, the ever-changing open-air gallery continues to provide a community space for advocacy along with cultural pride, hyper-local humor, and history. Look up and you’ll notice turret-flanked brick buildings and Bohemian baroque facades built by Eastern European immigrants who first settled here in the late 1800s. Browse galleries and shops for local art, and refuel at a taqueria or locally owned bakery.

Visit the final resting grounds of Chicago’s famous residents throughout history at Graceland Cemetery on the North Side. The 119 acres (48 hectares) of lush arboretum and elaborate tombs rivaling Buenos Aires’ Recoleta are a welcome reprieve to the densely packed surrounding neighborhood streets. While it's worth a visit just for the tranquil atmosphere, you can also explore with a guide. Learn about meatpacking tycoon Phillip Armor, department store innovator Marshall Field, and visionaries in Chicago architecture on a cultural history tour of this off-the-beaten-path attraction.

Did you know?: Spending an afternoon at Graceland really isn’t just for paying respects. You’ll encounter neighborhood residents walking their dogs, running, and relaxing under the trees.

The Northwest Side neighborhoods of Bucktown and Logan Square are filled with unconventional things to do in Chicago. Between award-winning cocktail bars, Michelin-starred restaurants, vintage shops, urban street art, and a never-ending stream of community festivals and outdoor markets, this part of the city is ideal for art lovers and foodies alike.

Insider tip: The Dave Jonasen, a 2.8-mile (4.4-kilometer) converted rail-to-trail multi-use path, connects Lincoln Park to Logan Square. As Chicago’s answer to New York’s High Line, the trail features intentional landscaping and public art, and situates you just a short walk to coffee shops and restaurants.

Stretching more than 18.5 miles (30 kilometers) along the shores of Lake Michigan, the Lakefront Trail beyond the Loop is full of hidden gems in Chicago. Head north to the Montrose Point Bird Sanctuary, a 15-acre (6-hectare) hub for more than 300 species of migratory birds and photo-worthy views of the Chicago skyline, or head south for restored prairie grasslands and wildflowers in the Burnham Wildlife Corridor. If you're looking to cover the most scenic ground, bike tour is one of the best ways to experience the nature and public art along the trail.

Chicago-style dogs, Italian beef, and deep-dish pizza may be delicious, but Windy City cuisine is far more extensive than just these three well-known handhelds. You’ll work up an appetite on a bike and food tour passing through West Side neighborhoods, such as West Loop, Ukrainian Village, and Old Town, before tucking into some lesser-known but still-beloved Chicago staples. Savor Polish pierogies, gourmet pizza, and tacos—three Chicago staples locals swear by.

Related: 10 Quintessentially Chicago Dishes and Where To Eat Them in the Windy City