29. Black Dog
Location: 859 North Damen Ave.
With off-the-wall flavors such as sesame fig chocolate chip and goat cheese cashew caramel, this gourmet gelato locale gives Italy a run for its money. And the whiskey gelato bar (yes, whiskey, plus gelato, on a stick) may be as close to paradise as you'll get in this life.
(For other great food 'n booze combos, check out this list of 20 Great Booze-Infused Foods from Across America.)