The "Neighborhoods in Chicago" Wikipedia page alone lists more than 'hoods and so-called "community areas" that overlap more than the Marvel universe's storylines.
Mexican Bars and Clubs.
All these are meant for adult entertainment.
If it's summer festival season think Pride and Market Daysgoing out in Boystown is usually a recipe for a hour blackout binge.
If an old man or a pregnant woman gets on your bus and you're sitting in one of the handicap seats, get up and stand or be prepared to have six different people yell at you until you do.
Kokoroko A funky Wicker Park vintage shop so steeped in 90s nostalgia that it could legitimately be a forgotten Nickelodeon Studios gift shop.
Grab a giant Mexican pastry at the self-serve Nuevo Leon Bakery and take a long walk around to do some mural peeping.