Bread pudding emerged from obscurity in the 13th century as something called poor man’s pudding; then it cross-pollinated with custard in the United States in the 1800s. However you slice it, the dish has humble beginnings: Most recipes call for dry, day-old bread, which gets soaked in a variety of sinful mixtures anchored by eggs, milk, and butter. A turn in the oven delivers a satisfying—if artery-hardening—treat. You might want to lose the belt before cozying up to our list of the best. 

 

Bread pudding ingredients: butternut squash, cinnamon, butter, dark chocolate and cherries, fruitcakeM. HENRY
OUT OF THIS WORLD BREAKFAST BREAD PUDDING ($6.75; $5.25 for a half order)
5707 N. Clark St.; 773-561-1600
THE BREAD Egg brioche
THE PREP Milk, eggs, heavy cream, vanilla
THE PUDDING This legendary specimen sports a crown of warmed peaches and blackberries. Is it breakfast? Dessert? We don’t care.

 

PITCHFORK
BOURBON BREAD PUDDING ($6)
2922 W. Irving Park Rd.; 773-866-2010
THE BREAD Brioche
THE PREP Eggs, heavy cream
THE PUDDING Pitchfork tosses tart Granny Smith apples and golden raisins into its buttery pudding, but remember, it’s a whiskey bar: Beware the killer bourbon and brown sugar glaze.

 

HEARTY
BUTTERNUT SQUASH BREAD PUDDING APPETIZER ($9)
3819 N. Broadway; 773-868-9866
THE BREAD Cubed brioche
THE PREP Eggs, cream, roasted and puréed butternut squash
THE PUDDING Made with sautéed shallots, sage, and Fontina cheese and served with truffle fondue, this savory bread pudding is built to start your meal—not end it.

Warmed peaches and blackberries, Granny Smith apples and golden raisins 

MRS. MURPHY AND SONS IRISH BISTRO
BREAD PUDDING ($7)
3905 N. Lincoln Ave.; 773-248-3905
THE BREAD Brioche
THE PREP Bread tossed in melted butter, toasted, and drenched in custard
THE PUDDING This wonderfully moist bread pudding, classically presented with a Bushmills Irish whiskey and caramel sauce and cinnamon mascarpone cream, is our favorite. Must be the butter.

 

SOUTHPORT GROCERY AND CAFÉ
BREAD PUDDING PANCAKES ($9)
3552 N. Southport Ave.; 773-665-0100
THE BREAD White bread
THE PREP Milk
THE PUDDING Who knew that bread drenched in milk would make pancake batter so moist and divine? Warning: Thanks to SG’s signature cinnamon-sugar butter and a side of vanilla custard sauce, it’s insanely sweet.

 

Bread pudding ingredients: butternut squash, cinnamon, butter, dark chocolate and cherries, fruitcakeSUZETTE’S CRÊPERIE
CHOCOLATE CHERRY BREAD PUDDING ($4)
211 W. Front St., Wheaton; 630-462-0898
THE BREAD Chunks of day-old brioche, pretzel bread, and croissants
THE PREP Milk, eggs, seriously heavy cream
THE PUDDING With a lovely filling of dark chocolate and something resembling cherry pie—and an unprecedented amount of fat—this is easily the most sinful of the bunch.

 

GAETANO’S RESTAURANT
PANETTONE BREAD PUDDING ($7)
7636 Madison St., Forest Park; 708-366-4010
THE BREAD Sliced traditional Italian sweet bread speckled with raisins and candied pumpkin, orange, and lemon
THE PREP Egg yolks, cream
THE PUDDING Topped with vanilla semifreddo and chocolate sauce, panettone lies somewhere between fruitcake and ice cream sundae. Fine by us.

 

Photography: Anna Knott