Valentine's Day Run 5K/10K/13.1 CHICAGO/EVANSTON

Valentine's Day Run 5K/10K/13.1 CHICAGO/EVANSTON takes place in Chicago, Illinois, on February 13, 2027. Four distances share a 7:30 a.m. start, a half marathon (13.1 miles), a 10K, a 5K and a one-mile family fun run, and the route is punctuated by chocolate stations, cheering volunteers and places to stop for photos. Finish in person and you collect a race shirt, a participant kit and a finisher medal, with treats waiting at the end; a virtual entry is available as an alternative.

Mid-February in Chicago sits deep in the winter training season, which is part of the appeal: the race gives you a reason to keep the long run on the calendar through January. The half suits runners with a base already in place, while the 10K rewards a shorter, sharper build. Newcomers should not be put off by the distances on the banner, since the one-mile fun run counts too.