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Chicago, IL

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In season through November 30part of Fall in Chicago

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Editor’s picks

Press picks, until locals rank their own Top 5s. Sourced from the local food press. As seen in Time Out Chicago. Updated September 2026.

Hoosier Mama Pie Company · West Town
Paula Haney, a former fine-dining pastry chef, made a name for her pies at farmers markets and coffee shops before settling into this tiny, retro pie shop. The case follows the seasons, from strawberry-rhubarb in spring to apple and pumpkin in fall, alongside house signatures such as the banana cream and the Chicago Sunrise, a pie inspired by Malört. Metropolis coffee is poured to go with a slice. Order the banana cream.
Bang Bang Pie & Biscuits · Logan Square
The flavors at this Logan Square pie shop rotate regularly, following seasonal produce and turning out funky combinations for the holidays. Summer can bring a lemon pie layered with tangy lemon cream, frothy lemon mousse and lemon curd, and winter richer creations like an apple and raspberry crumble. Key lime stays on all year: a citrus custard poured into a graham cracker crust and topped with a dollop of fresh whipped cream. Order a slice of the Key lime.
Justice of the Pies · Avalon Park
Maya-Camille Broussard started Justice of the Pies to honor her late father, a criminal defense attorney and a self-proclaimed pie aficionado. Her slices are sold at this bakery in Avalon Park and through pop-up partners around the city, and the business partners with nonprofits to make a positive difference in the lives around it. Order the lavender-lemon pie.
Gibsons Bar & Steakhouse · Gold Coast
The macadamia turtle pie at this Rush and Division steakhouse is the dessert that catches every eye in the dining room when it comes out: a pie crust loaded with vanilla ice cream, graham cracker crumbles and macadamia nuts, the towering dessert finished with drizzles of chocolate and caramel sauce. It is built to be shared. Order one for the table.
Shaw's Crab House · River North
The Key lime pie at this River North seafood house comes on an almond-graham cracker crust with a buttery-smooth filling, and for a fruit pie, the raspberry is stuffed with berries from Mike & Jerry's berry farm in Washington state. Order the Key lime, or the raspberry for something fruitier.