Chicago Scavenger Hunt – Hard Mode

This is our Chicago scavenger hunt on hard mode, mobile-friendly and free so that you can take it with you while on the hunt. You can review the rules, our suggestions, and scoring on our original checklist-style Chicago scavenger hunt page.

Remember that you can click or tap each item to mark it as complete, as well as drag and drop rows to change the order of items.

Scavenger Hunt for Chicago

ItemPoints
Millennium Park — A reflective sculpture commonly known as “The Bean” offering a unique view of the city’s skyline.5
Millennium Park — Two 50-foot glass towers displaying LED images of locals with water flowing from their mouths.3
Grant Park — A large ornate fountain one of the largest in the world with impressive water displays.4
Daley Plaza — A massive abstract steel sculpture created by a famous Spanish artist.4
Federal Plaza — A bright red abstract steel sculpture by a renowned American artist.4
Grant Park — A series of 106 headless armless iron sculptures walking in various directions.3
Chase Tower Plaza — A vibrant mural depicting the changing seasons created by a famous Russian-French artist.4
James R Thompson Center — A large abstract fiberglass sculpture by a French artist known for its intricate shapes.3
Grant Park — Two bronze equestrian statues representing Native American warriors.5
Jackson Park — A gilded bronze statue commemorating the 1893 World’s Columbian Exposition.4
Washington Park — A large sculpture representing the passage of time featuring figures moving towards an imposing central figure.3
Loop — A surrealist sculpture by a famous Spanish artist known for its vibrant colors and whimsical shapes.5
Pioneer Court — A statue honoring the Haitian-born trader regarded as the founder of Chicago.5
Daley Plaza — A bronze flame dedicated to the memory of those who served in the armed forces.4
Bronzeville — A granite and bronze memorial commemorating the achievements of an African American infantry regiment in World War I.5
South Loop — A series of large-scale paintings created by local and international artists transforming the area into an open-air gallery.3
Lincoln Park — A vibrant painting of flamingos created by a well-known street artist adding color to the urban landscape.4
Magnificent Mile — A large reproduction of the famous painting displayed on the exterior of a building.4
Grant Park — Two bronze lion sculptures guarding the entrance of a famous art museum.3
Loop — A historic and iconic neon sign of a well-known theater perfect for photos.4
Loop — A glass-floored observation deck offering thrilling views from one of the tallest buildings in the Western Hemisphere.4
Streeterville — A large Ferris wheel providing scenic views of the city and Lake Michigan.4
Magnificent Mile — A historic skyscraper with stunning architecture and a clock tower beautifully lit at night.5
River North — Two iconic cylindrical towers known for their unique design and scenic views of the Chicago River.4
Lincoln Park — A beautiful glass building housing exotic plants and flowers providing a peaceful escape in the city.4

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