Top 10 Things to Do in Chicago

1. Explore Millennium Park

Millennium Park is a 24.5-acre civic park in Chicago’s Loop that opened in 2004 after a major redevelopment of former rail yards and parking lots. The site is known for Cloud Gate, the stainless-steel sculpture by Anish Kapoor, and Crown Fountain, the dual glass-block towers designed by Jaume Plensa. The Jay Pritzker Pavilion, designed by Frank Gehry, functions as the park’s main outdoor performance venue and is home to the Grant Park Music Festival summer season. Millennium Park sits between Michigan Avenue and Columbus Drive within Grant Park, linking downtown office districts to lakefront public space and large-scale public art installations.

2. Explore Navy Pier

Navy Pier extends about 3,300 feet into Lake Michigan and first opened in 1916 as Municipal Pier No. 2, designed by architect Charles Sumner Frost. During the 20th century it served shipping, passenger, military, and university functions before being redeveloped as an entertainment and event complex. The pier includes festival halls, theaters, restaurants, boat docks, and the Centennial Wheel, installed in 2016 during the attraction’s centennial renovation cycle. Located just east of Streeterville, Navy Pier remains one of the most visited destinations in the Midwest and reflects Chicago’s long relationship with lakefront commerce, public recreation, and large civic infrastructure projects.

3. Explore Art Institute of Chicago

The Art Institute of Chicago was founded in 1879 and is one of the oldest and largest art museums in the United States. Its main Beaux-Arts building on Michigan Avenue opened in 1893 for the World’s Columbian Exposition and is identified by the two bronze lion sculptures at the entrance. The museum holds major collections spanning ancient Mediterranean objects, Asian art, European painting, American modernism, and architecture and design archives. Notable works include pieces by Monet, Seurat, Grant Wood, and Edward Hopper. The institution is also connected to the School of the Art Institute of Chicago, making it a central part of the city’s long-standing visual arts and education network.

4. Explore Riverwalk

The Chicago Riverwalk is a multi-level pedestrian waterfront along the south bank of the main branch of the Chicago River in downtown Chicago. Its current form was completed in phases, with major expansion work between 2012 and 2016 that widened public access from Lake Shore Drive west toward Franklin Street. The corridor is organized into distinct sections, including the Marina, Cove, River Theater, and Civic zones, each designed for different uses such as boating, seating, and events. The Riverwalk sits below Wacker Drive, directly adjacent to high-rise architecture, and provides close views of bridges and historic buildings that define Chicago’s central river canyon.

5. Explore Wicker Park

Wicker Park is a Chicago neighborhood on the city’s Northwest Side centered near the intersection of North, Damen, and Milwaukee avenues. The district developed rapidly in the late 19th century after the 1871 Chicago Fire, when many residents and businesses moved outward from denser central neighborhoods. It takes its name from the 4-acre Wicker Park, donated in 1870 by brothers Charles and Joel Wicker. In the 1980s and 1990s, the area became associated with independent music venues, galleries, and artist lofts in former industrial buildings. Today Wicker Park combines historic housing stock, commercial corridors, and rapid-transit access via the CTA Blue Line station at Damen.

6. Explore Lincoln Park

Lincoln Park is Chicago’s largest public park, stretching roughly 7 miles along Lake Michigan from Ohio Street Beach to near Ardmore Avenue. Originally designated as a cemetery area in the mid-19th century, it was renamed for Abraham Lincoln in 1865 and gradually transformed into landscaped recreation grounds. The park includes the Lincoln Park Zoo, founded in 1868, and the Lincoln Park Conservatory, opened in the 1890s, alongside beaches, athletic fields, and harbors. Its long linear footprint connects multiple neighborhoods on the North Side and preserves significant lakefront open space. The park is managed by the Chicago Park District and remains a core element of the city’s shoreline planning.

7. Explore Willis Tower Skydeck

Willis Tower, completed in 1973 as the Sears Tower, rises 1,450 feet (442 meters) to its roof and was the world’s tallest building until 1998. The Skydeck observatory is located on the 103rd floor at about 1,353 feet above street level, offering wide views across Illinois and into neighboring states on clear days. In 2009, the observation deck added The Ledge, a set of glass boxes extending outward from the façade. The tower was designed by Bruce Graham and structural engineer Fazlur Rahman Khan of Skidmore, Owings & Merrill using a bundled-tube system. The Skydeck remains one of Chicago’s most recognized high-rise observation experiences.

8. Explore Architecture River Cruise

Chicago architecture river cruises travel the main, north, and south branches of the Chicago River and interpret the city’s built environment from water level. Commercial tours began in the 20th century and expanded as riverfront access improved and architecture tourism became a major part of Chicago’s visitor economy. Routes typically pass landmarks such as the Wrigley Building, Merchandise Mart, Marina City, and modern supertall towers in the Loop and River North areas. Many operators collaborate with trained docents or architecture organizations to explain planning history, engineering systems, and stylistic shifts from the 1880s through the 21st century. The format highlights how bridges and river geometry shaped downtown growth.