Chocolate Cake Shake from Portillo’s—Yes, you read that right. This Chicago-style hot dog joint offers perhaps the best dessert combination ever, the chocolate cake shake. Vanilla ice cream is blended with Portillo’s decadent chocolate cake for a thick shake combination that will take you back to your childhood.Churro Sundae from Churroholic
—Crispy fried churro pieces are the base of the churro sundae at Churroholic
and it gets even better from there. They take two original churros, cut them into bite-sized pieces, and top them with ice cream, whipped cream, caramel, chocolate, coconut flakes, and toffee. Bring a friend as there’s more than enough to share.