Indulge in a raspberry truffle shake from Bobtail Ice Cream before exploring funky shops, such as Hollywood Mirror, selling off-the-wall gifts like cupcake pillows. It’s also known for drawing foodies with unique establishments, such as the Chicago Diner, which has been serving vegetarian comfort food since 1983 (the Cajun black bean burger is a perennial favorite). A Legacy Walk of rainbow-color totems with plaques honoring LGBTQ rights advocates lines the main thoroughfare of this anchor to Chicago’s gay scene.