Harper Avenue from 57th to 59th, Hyde Park
You’ll find spiders falling from rooftops and trees, creepy-as-is Victorian homes covered in skeletons, a giant worm smack in the middle of the street, and, some years, a homemade horror character known as “The Thing.” The area is well prepared for the onslaught of kids: Roughly 2,000 pieces of candy are dished out at each residence.
Goethe Street from Dearborn to Astor, Gold Coast
Mansions become professionally decorated haunted houses, crowned with giant spider nests and, in one case, a witch stirring a big cauldron you might just get tossed into. Expect huge candy bars and stuffed animals as treats. Keep your eyes peeled: J.B. Pritzker has been known to pass out sweets at his manse on Astor.
Burling Street from Fullerton to Wrightwood, Lincoln Park
This stretch, packed with single-family homes, is blocked off for safe, efficient trick-or-treating. Front yards are transformed into graveyards, and some families have been known to give snacks like Italian beef sandwiches to grownups too.