Posted in Route 66 sign The Start/End of Route 66 in Chicago, IL sysadmin June 23, 2018 Leave a comment The Gateway of Route 66 Starts/Ends in Chicago, IL Route 66 Starts at Gateway Intl Raceway and goes westward from there. Share this:Click to share on Twitter (Opens in new window)Click to share on Facebook (Opens in new window) Author: sysadmin Related Articles One Route 66 But Many Names Another Street Sign Ride along with us!