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Chicago Route 66 Start of the Trail Sign

Choose Chicago blog post

Route 66 Association of Illinois

Chicago Navy Pier website

Illinois Route 66 Scenic Byway article

Route 66 Road Trip article

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Location Details

Route 66 start sign in Chicago is located on East Adams Street just west of South Michigan Avenue, alongside a new symbolic starting point introduced at Navy Pier. 

Historic Starting Spots (Downtown)

  • Begin Sign: Mounted on East Adams Street (facing west-bound traffic) right across from the Art Institute of Chicago at 122 S. Michigan Ave.

  • Alternative Signs: Additional markers sit nearby on Adams Street mid-block and at the corner of Adams and Wabash Avenue.

  • End Sign: Located just one block south on the south side of East Jackson Boulevard at South Michigan Avenue (facing east-bound traffic).

New Symbolic Start (Navy Pier)

  • Location: Navy Pier at 600 East Grand Avenue.

  • Details: Designated as the official modern pier-to-pier ceremonial start matching the Santa Monica Pier, featuring a "The Road Begins Here" sign in front of Harry Caray's Tavern.

  • Cost & Access: Free to visit outdoors 24/7 (indoor pier venue hours vary).

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