5. Chicago, IL

Chicago, IL

Courtesy of Christkindlmarket Chicago

Chicago’s frosty winter weather, festive events, and glittering lights make it a hotbed for holiday spirit. The 20th annual “Magnificent Mile Lights Festival” is at the city’s celebratory epicenter, where more than a million lights on 200 trees flank the famous shopping strip, with hundreds of shop’s holiday window displays adding to the appeal.

Don’t miss stepping in to see Macy’s 45-feet-high Great Tree, whose lights remain up through March 1 (free; www.themagnificentmile.com). Meanwhile, downtown’s sparkling Christmas tree in Daley Plaza has been prettifying this plaza for 98 years; a Santa’s workshop for the kids and German-style Christmas market ensure the square is positively brimming with holiday cheer (remains lit through January 8; free).