Chicago, ILHot Chocolate

A Logan Square confectioner with a case of chocolates, candy and house-made marshmallows, but The Infatuation says the reason to come is the drink: ground chocolate melted into a mix of milk and cream, which lands velvety and almost buttery. Flavours run to hazelnut and salted caramel. Order the twelve dollar flight of three rather than a single cup, which is the guide's own advice and the only way to taste across the range in one sitting.

The River North cafe of the New Hampshire chocolatier pours several drinking chocolates, some made with single-source chocolate shavings. The Infatuation is unambiguous about which one to pick: the spicy dark cocoa, served piping hot. It has the thick consistency of a drinking chocolate but runs sweeter, and a hint of chili pepper balances it out. Order that rather than working through the range, and note that the guide rates the lineup highly enough to propose replacing the Chicago River with it.

A tiny Pilsen sweets shop The Infatuation describes as a jewel box, where the black salt caramel truffles and the sipping chocolate are both worth the trip. A handful of flavours rotate through, including plain, a seasonal pumpkin spice and a more unusual turmeric. Order the rose, which the guide rates the best of them: the dried petals scent the chocolate without taking it over. The cup is well balanced rather than heavy.

The Wicker Park bakery comes from the team behind Mindy's Hot Chocolate, the closed restaurant that was named for this exact drink, and The Infatuation reports the classic version survived the move. Twelve dollars buys a single cup of mild liquid chocolate that reads sweet without being cloying, thick but still drinkable, plus a house-made marshmallow the guide singles out. Order it alongside whatever is in the pastry case that morning.

An all-day cafe and bakery on North Clark Street that The Infatuation describes as diner-ish, and the only neighbourhood spot on this list rather than a chocolate specialist. The cocoa is the reason it is here: thick, creamy, and in the guide's words tasting like a melted chocolate bar. Order a mug with something from the bakery counter, which is what the room is set up for. The city inspection register recorded a pass at this address in May 2026.