Why Go: The Windy City embraces yuletide cheer to the max, with a million holiday lights along bustling Magnificent Mile; Christkindlmarket, a huge outdoor German crafts market with beer and fare like sausages to stoke your fire; a towering handmade Christmas tree; and Navy Pier’s Winter WonderFest, a holiday-themed amusement park and indoor skating rink.
Where to Stay: Peppy, tropical-themed Hotel Monaco Chicago is a Kimpton boutique hotel with verve and a sense of humor. Its wild combo of lime and plum is eye-popping, and it’s a great value in The Loop.
Holiday Dinner: Cozy wine-driven eatery the Cellar at Bin 36 is serving its creative, locally sourced menu on Christmas Day. Starter highlights like Applewood smoked bacon are followed by the likes of a cedar-plank salmon with beluga lentils and pork schnitzel with butternut squash spaetzle. Expert wine pairings are, of course, de rigueur.
The windy city is a cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans. Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. There are dozens of museums and theater companies in Chicago, so a cultural experience is never hard to find. You’re sure to laugh your head off at the Second City Theater, the professional launch pad of many famous comedians.