Chicago Diabetes Project, Chicago

If people hear a collective gasp rush through Gold Coast on December 7, they will know it’s 11 a.m. That’s when the open bar begins and hordes of fun-loving, mildly masochistic do-gooders hit the winter streets in nothing but their skivvies to raise funds and awareness for diabetes. Then at 1 p.m., gussied up—or down—in holiday-themed speedos, runners will tear through a mile of the highbrow neighborhood, giving residents something to talk about other than their displeasure with the gelato in Mariano Park.