In 2004, because of the cancellation of the NHL season, Chelios, along with fellow Red Wing teammates Derian Hatcher and Kris Draper, decided to play hockey for the Motor City Mechanics, a UHL team based out of Fraser, Michigan. He was heavily criticized for this decision as the UHL has a maximum salary in place, but at the same time he was strongly against a salary cap in the NHL. In October 2004 he trained with the U.S. bobsled federation in a bid to compete for the Greek bobsled team at the 2006 Winter Olympics. While Chelios didn't compete in the bobsled, he did captain the USA hockey team at the 2006 Winter Olympics in Turin, Italy.
Through his career, Chelios has befriended many non-hockey athletes and entertainers. In 2004, he and surfer Laird Hamilton trained with the U.S. bobsled team and hoped to form the first Greek bobsled team at the 2006 Winter Olympics. Chelios and his family can be found Stand up paddle surfing with Hamilton. Chris credits the activity with helping him maintain his long career.
On Scrubs, Dr. Perry Cox, played by Chelios' friend John C. McGinley, often wears a Red Wings jersey with Chelios' name and number. During the fourth season of the show, which was concurrent with the 2004–05 lockout, Cox was seen on at least one occasion wearing a No. 24 "Motor City Mechanics" jersey. Chelios is also close friends with actors John Cusack and D. B. Sweeney, Pearl Jam frontman Eddie Vedder, Smashing Pumpkins frontman Billy Corgan, and musician Kid Rock. Chelios was sitting courtside with Kid Rock during the Pacers-Pistons brawl at the Palace of Auburn Hills on November 19, 2004. Chelios and Sweeney are quite close, with the two having appeared together in The Cutting Edge (1992) and Two Tickets to Paradise (2007), in addition to Chelios being the godfather to Sweeney's son, Cade.