Originally scheduled for late October or early November, the contest had to be postponed because of the eighty-nine entries, only a handful were ready to go. The race was rescheduled for Thanksgiving Day, November 28. On November 2, the newspaper held a consolation event for those ready entrants. During this event, the Duryea went into a ditch to avoid a farmer's wagon and was severely damaged. The automobile was returned to Springfield for repairs with only a few weeks before the big race. The vehicle that did win the consolation event, with an engine built by Benz, was that of H. Mueller and Company.
As fate would have it, snow fell the evening of the race. The morning light revealed slippery, deeply-rutted roads, bounded by huge snowdrifts. That Thanksgiving morning, only six vehicles were at the starting line; the Duryea, two Benz automobiles including one sponsored by the Macy department store in New York, two electric vehicles, and the car of H. Mueller and Company (with a reconstructed engine).
The race course ran from Chicago to Evanston and back, a distance of about 50 miles (80km). The November cold and the terrible road conditions took their toll early. The two electrics dropped out as their batteries died. The two Benz automobiles also broke down. The Duryea, however, made consistent, steady progress, but at a rate of under 10 m.p.h. It crossed the finish line just after 7 pm. An exhausted Frank Duryea climbed down from the vehicle. He had been driving for over nine hours.
Just before 9 pm, the Mueller vehicle, with its weary passengers nearly overwhelmed by the cold, arrived at the finish line.