Best Places for Pie

You've probably crafted at least one excuse to eat pie, but we have five reasons to indulge at Chicago's best pie shops. Whether you like it custardy, fruity or a la mode, there's no reason not to treat yourself to one (or more) of these toothsome slices.

Updated: March 16, 2010

Chicago Pie Stops


1327 E 57th St, Chicago, IL 60637

Pie purists swoon over Gracie's apple pie, a thick wedge of crispy crust and tart chunks of fruit that's served warm with an oozing dollop of vanilla ice cream at this sweet Southside standby. If one slice leaves you wanting more, snag a whole pie from adjoining Medici's Bakery.

Hoosier Mama Pie Company

1618 1/2 Chicago Ave, Chicago, IL 60622

Slip into West Town's sunny slice of pie nirvana for a cup of Metropolis coffee and some lemon chess pie--a custardy, pucker-inducing Southern classic. If you're feeling benevolent, surprise your office mates with a tangy strawberry rhubarb or passion fruit meringue pie.

Sweet Mandy B's

1208 W Webster Ave, Chicago, IL 60614

Even non-pie lovers can get their pie on thanks to this Lincoln Park sugar shack's whoopie pie, a colossal concoction that actually belongs in the cake family. Perched regally atop the bakery case, this sprinkle-covered affair sandwiches the bakeshop's beloved butter cream frosting between two slices of dense chocolate cake.

First Slice

4401 N Ravenswood Ave, Chicago, IL 60640

Down a decadent helping of this Ravenswood cafe's chocolate-peanut butter pie and forget that usual side of guilt since your indulgence just benefited someone in need. Fifteen percent of the cafe's proceeds benefit First Slice, a community-supported kitchen that provide restaurant-quality food to the needy. Now that's the spirit.

Tipsy Cake

1043 N California Ave, Chicago, IL 60622

If you're craving an out-of-the-ordinary pie on this unconventional holiday, call this Humboldt Park shop and ask for the made-to-order Banoffi pie. The layered creation starts with a crumb crust, alternates rows of fresh bananas and fudge, and ends with a mound of whipped cream drizzled with homemade toffee.