Dat Donut Credit: KidItamae via Flickr

Dat Donut
8251 S. Cottage Grove

This Chatham spot rolls out handmade doughnuts seven days a week and almost 24 hours a day—it briefly closes at 5 PM on Sunday. Next month Dat Donuts celebrates its 20th anniversary, which means thousands of doughnut purists have made the pilgrimage for the shop’s mammoth-size Big Dat.

Do-Rite Donuts
50 W. Randolph

Do-Rite’s Loop location is no more than a counter and a wall of doughnuts behind it. If you’re looking to make a meal of a doughnut, try the pistachio-Meyer lemon; the handfuls of toasted pistachios on top might make you feel less guilty.

Somethin’ Sweet Donuts
5112 W. Fullerton

This unassuming shop also sells smoothies, sandwiches, and hot dogs, but don’t let the hodgepodge menu fool you; Somethin’ Sweet’s plump and light doughnuts are the focus. The glazed blueberry has a bold sweet kick that lingered after I left the place.