Despite the frigid temperatures in Chicago during the holiday season, this city is one of the best places for getting into the yuletide spirit and meeting all your Christmas shopping needs. The city's boldest opening is the new branch of Eataly, Mario Batali’s 63,000-sq.-ft. Italian superstore that carries sweets, meats, cheeses, wines, olive oil, pasta and more.
You can also hit up the German-style Christkindlmarket downtown for mulled wine, apple pastries and goulash, then go ice-skating and get hot chocolate in Millennium Park. Afterwards, take a break with high tea at The Drake Hotel. For more tasty holiday fun, hit up Irish saloon Butch McGuire’s, where the over-the-top Christmas decorations are an annual tradition. For something a bit fancier, try Lawry's Prime Rib, which is housed in an 1890s-era mansion.
Where to stay: Indulge in the luxurious world of The Drake Hotel, which has single, double and family-sized rooms complete with a mini bar, large HDTV and cozy bathrobes to lounge in. Sip a bit of history at the speakeasy-style Coq d’Or bar, a classic spot that opened its doors right after Repeal Day in 1933, the same year the hotel opened the seafood restaurant Cape Cod. Rates start at $199