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Best Places to Visit in Chicago

Chicago

Whether you're visiting Chicago for the first time or discovering something new, these are the 38 places worth your time, from iconic landmarks to hidden corners that most visitors walk right past. With Questo's self-guided walking tours, you can explore many of them with GPS-guided clues and puzzles.

Explore Chicago with Questo

Discover Chicago's best places with a self-guided walking tour. Follow GPS-guided clues, solve puzzles at landmarks, and uncover stories most visitors miss — all at your own pace.

Browse 21 walking tours in Chicago

All 38 places to visit in Chicago

Explore the top landmarks, attractions, and hidden gems in Chicago

The Art Institute of Chicago

The Art Institute of Chicago is one of the oldest and largest art museums in the United States, and it sits right in the middle of the…

Crown Fountain

Crown Fountain is one of Chicago's most beloved modern public artworks, bringing together cutting-edge technology and playful interactive…

Cloud Gate

Cloud Gate stands as Chicago's most photogenic landmark, a 110-ton sculpture of polished stainless steel that seems to float in AT&T Plaza.…

BP Pedestrian Bridge

The BP Pedestrian Bridge curves gracefully above Columbus Drive, serving as both functional infrastructure and sculptural artwork in the…

Chicago History Museum

The Chicago History Museum stands as the second-oldest museum in Chicago, preserving and sharing the stories that shaped one of America's…

Lincoln Park Zoo

Lincoln Park Zoo has been delighting Chicago families for over 160 years, making it one of the oldest zoos in the United States and one of…

Ping Tom Memorial Park

Ping Tom Memorial Park sits on the banks of the Chicago River, creating a vibrant riverfront destination that reflects the city's…

Tribune Tower

Tribune Tower stands as a Gothic masterpiece in the heart of downtown Chicago, representing the pinnacle of early 20th-century newspaper…

DuSable Bridge

DuSable Bridge spans the Chicago River connecting downtown to the Near North neighborhood, serving as both essential infrastructure and an…

Old Chicago Water Tower District

The Old Chicago Water Tower District is one of the few structures that survived the Great Chicago Fire of 1871, making it a significant…

Holy Name Cathedral Rectory

Holy Name Cathedral Rectory stands as a testament to Chicago's diverse architectural heritage and the complex history of faith communities…

Flying Dragon

Flying Dragon is a striking public art sculpture that adds vibrant color and kinetic energy to Chicago's urban landscape. Located in the…

Founders Wall

Founders Wall commemorates the visionary figures who established Chicago and shaped its trajectory from a frontier trading post into a…