Bar Toma The menu is hit or miss at Tony Mantuano’s casual pizza joint, and execution wavers, but our ideal meal would start with polpettes (plump shrimp meatballs in spicy tomato sauce), move on to a pizza (such as the inspired combination of goat cheese, hazelnuts, leeks and roasted dates) and end with a cup of the cioccolato caldo—thick, drinkable Peruvian dark chocolate mixed with milk, cream and sugar. 110 E Pearson St (312-266-3110). Breakfast, lunch, dinner. Average pizza: $13.
Black Dog Gelato The second outpost of Jessica Oloroso’s unique gelato shop is pretty much the same as the first, with a few minor exceptions: (1) This location feels more polished than the Damen Avenue shop. (2) This location offers more seating. (3) This location is the first of the two this season to offer Spanish-style drinking chocolate (with housemade marshmallows). Of course, both locations hawk Oloroso’s uncommonly smooth, rich-but-not-too-rich gelato, in flavors (strawberry-balsamic; cajeta) both wild and tame. 1955 W Belmont Ave (773-348-7935). Mon 7–10am; Tue–Fri 7–10am, 3–10pm; Sat, Sun 2–10pm. Average cup of hot chocolate: $4.
Sprinkles Cupcakes We’ve always preferred Sprinkles’ chocolate flavors of cupcakes over the non-chocolate ones (the chocolate peanut butter is insane; the vanilla is just insanely sweet). Turns out the cupcake shop is serious about chocolate in other forms, too. We’re talking about the bittersweet drinking chocolate topped with vanilla bean marshmallows. Pairing the drink with a chocolate cupcake is probably overload. But what the hell, we’ll risk it. 50 E Walton St (312-573-1600). Mon–Sat 9am–8pm; Sun 10am–7pm. Average cupcake: $3.50.
XOCO Breakfast at Rick Bayless’s most casual spot yet is quiet perfection: a cup of masterfully concocted hot chocolate, a flaky egg empanada, one hell of a sugar-and-cocoa-coated churro. Lunch here is no less delicious, but it’s a frenzy: Lines extend out the door for tortas filled with fatty, crispy pork carnitas. The crowds keep up at dinner, when caldos like braised-short-rib soup and chicken stew with toothsome posole are the ideal prelude to…another churro. 449 N Clark St (312-334-3688). Breakfast, lunch, dinner (closed Sun, Mon). Average main course: $11.