The Backyard Tourist

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Route 66 Start

Plan a Midwest road trip from the Windy City. Learn logistics, timelines, and routes that fit a long weekend or a full summer adventure.

Route 66 sign installed at Chicago's Navy Pier in 2026

Route 66 posts

  • Springfield — Walking in Lincoln’s Footsteps
  • Day 3: Springfield — Where Route 66 Meets Lincoln’s Legacy
  • Day 2: Bloomington to Springfield — Lincoln, Landscapes, and the Living Legacy of Route 66
  • One Tank Trip from Chicago: Route 66, Roadside Icons, and Small-Town Stories
  • Route 66-Pontiac, IL
  • Museums Drive the Economy in Pontiac, IL
Ferris Wheel and Swings at Navy Pier
Buckingham Fountain, Grant Park Chicago
The Chicago River at night
Chicago skyline as viewed from Millenium Park

Route 66 Chicago

Begin your Route 66 journey in Chicago with practical tips, a realistic timeline, and key logistics to balance driving time with must-see stops.

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