Named one of the “best Christmas towns in America”: This Illinois town’s holiday season returns November 20 with a festive kickoff
It goes without saying there is no shortage of holiday events in Chicago , from bars adorned with floor-to-ceiling decorations to lights taking up an entire zoo—we mean there’s even a returning Little Nero’s-themed pizza pop-up inspired by Home Alone . But don’t let Chicago hold you hostage this holiday season; there are so many fun things happening outside the city limits . One of them is in historic downtown Long Grove, named one of the best Christmas towns in America (and only an hour from Chicago, might we add). Every year, the town transforms into something that feels like a Hallmark movie: storefronts are decorated with festive displays, carolers hit the streets, and carriage rides are the main form of transportation. Officially called Vintage Holidays, the annual event returns November 20 through December 24, 2026. Vintage Holidays begins with Light Up Long Grove The season opens Friday, November 20, with Light Up Long Grove from 5–8 p.m. Shops will stay open late, with decorated, tractor-pulled wagon rides, illuminated photo stations, and street activities running from 5–7:30 p.m. At 7:30 p.m., the village will light its bridge and Christmas tree, followed by a performance from the Fred Astaire Dancers. Consider