Chicago officials met with NASCAR representatives to discuss the potential return of the Chicago Street Race in 2027, with a focus on improved set up and tear down efficiency, financial impact, and community engagement.

Downtown construction forced the fourth stop of the annual Chicago Grit bicycle road racing series to carve a new course Monday in Mundelein. The Tighthead Mundelein Grand Prix moved it’s 9/10th of

Whitehawk, a 104-foot wooden ketch, was the first to cross the finish line on Sunday. But given the conditions, some racing boats may not arrive at the island until Tuesday.

Nearly 300 boats participate in the Chicago Yacht Club Race to Mackinac, braving storms for a historic sailing competition.