Chicago Loop and Millennium Park Tour

Defined by the elevated train lines that form a circuit in the heart of the city, the Loop is Chicago’s downtown area and commercial core, home to big names such as Boeing and IBM. But, it’s so much more. The Loop contains the largest concentration of skyscrapers, including the tallest in the United States (not counting spires) and it is effectively a living architectural museum, with a large range of architectural styles, from Victorian to post-modern, many with grand interior spaces.  Alongside the buildings, thought provoking public art displays, such as an unnamed piece from Picasso, dot the landscape.  The Loop is also home to Chicago’s Theater District.

Join Free Tours by Foot on this fun and engaging walk through the Chicago Loop.  Come and learn about how the Great Fire of 1871 started and marvel at the modern city that rose upon the ashes of the old city, or learn about the country’s second largest “subway” system.  Take a selfie at the start of the legendary Route 66 and discover the Chicago Pedway, a mostly subterranean system of walkways that connect a large swath the Loop and beyond and a popular place for residents and workers during Chicago’s rough winters.  This tour ends in Millennium Park, Chicago’s still new and much loved public park.

Sights and topics we cover on the Loop and Millennium Park Tour:


  • Marshall Fields
  • The Picasso/Daley Plaza
  • City Hall
  • Marquette Building
  • Willis Tower (a.k.a. Sears Tower)
  • The Chicago Pedway
  • Millennium Park
  • Crown Fountain
  • The Great Fire
  • The L (elevated trains)
  • Start of Route 66
  • The Art Institute of Chicago
  • Cloud Gate (a.k.a. the Bean)


Tour information

Reservations: REQUIRED. Click here to reserve. Groups of 6 or more must contact us before booking.

Where: under the overhang of the Chicago Theatre, 175 North State Street, Chicago, IL, United States. (map)

Duration: Tour lasts approx. 2 hours. Total walking is just over one mile (1.6km).

When:  View our Calendar. Tours are on U.S. Central Standard Time.

Cost: This tour is free to take, and you get to decide what, if anything, the tour was worth when it’s done. A name-your-own-price tour is a tour for anyone’s budget.