Sweeten Up Your Holiday Spread with Chicago’s Best Pie Shops

Chef Kyleen Gray held executive pastry chef positions at some of Chicago’s premier restaurants before launching her own business, which focuses on a wide array of French delicacies and cakes. Pies make an occasional appearance, too, including during the holidays, when she’ll be making one of her favorites: Chocolate Silk, with a thin layer of chocolate ganache, chocolate pastry cream, whipped cream, and chocolate shavings. While you’re at it, grab a cookie box—her seasonal assortment features more than a half dozen varieties, from Ginger Molasses and Chocolate Crinkle to Alfajores and Pinwheels.
Cost: $$$
How to order: Inquire and order via Instagram.

A cherished choice citywide thanks to its homestyle baked goods—namely the pristine, pastel-frosted cupcakes—this bake shop places a premium on old-fashioned sugar fixes, and pie is no exception. Look for Key Lime, Banana Cream, Chocolate Cream, Apple Streusel, and fruit pies like Apple Cherry and Apple Blueberry on a regular basis, and this month, expect to see Pumpkin or Pecan in the rotation. If you’re making the trip, spring for a few other holiday musts, like Gingerbread, Candy Cane Brownies, or (epic) Iced Molasses Cookies.
Cost: $$
How to order: Order pick-up via Toast.

Since reopening their doors earlier this year, this Lincoln Park café and bakery has been hard at work serving a fleet of fan favorites, from Basque Cakes and Buckwheat Scones to quiche and croissants. This month, that lineup gets even more exciting with additions like Eggnog Canelés and Stollen, plus an of-the-moment pie: Gingersnap Lime, comprised of a spicy gingerbread cookie crust that’s filled with sweet lime custard and topped with whipped white chocolate ganache and citrus zest. Hello, holidays.
Cost: $$
How to order: Stop by for counter service or pre-order holiday pick-up via Tock by 5 pm on December 18.

This Lakeview bakery is known for their cakes, but they’ve got plenty of other sweet tricks up their sleeve, too, including a game-changing Door County Sour Cherry. For the holidays, they’re also offering an Apple Streusel or Chocolate Cream Pie, plus several other seasonal favorites like Panettone, Peppermint Meringues, Eggnog Cheesecake, and Sugar Cookies.
Cost: $$
How to order: Stop by for counter service or pre-order holiday pick-up online by December 17.

Pie is the specialty at this Logan Square go-to, which typically serves up to a half-dozen different kinds around-the-clock. Expect their signature Key Lime year-round, along with a fruit pie that rotates based on seasonality thanks to local purveyors like Michigan’s Mick Klug Farm. This month, that menu revs up significantly, with options like Candy Cane S’mores, Sweet Potato, Chocolate Hazelnut, and an uber-Insta-worthy Cornflake Wreath.
Cost: $$
How to order: Pre-order holiday pick-up online.

Chefs Genie Kwon and Timothy Flores recently debuted dinner service at their bustling bakery-meets-modern Filipino restaurant, which quickly rose to fame for its daytime fare of irresistible breakfast sandwiches and adobo. All the while, their pastries alone are reason enough to rush here. Kick things off with any of Kwon’s croissant renditions (namely the Apple-Cheese), along with the show-stopping Ham and Cheese Danish, a salty-sweet symphony that continues long after the first bite. Pies are part of the holiday plans, too, with four kinds on offer: Lemon Pecan, Chocolate Cremeux, Chocolate Pecan, and Pumpkin.
Cost: $$
How to order: Stop by for counter service or pre-order holiday pick-up and delivery via Tock.

A marble bar dating to 1928, reclaimed materials, and mix-and-match flatware are all part of the charm at this modern-day soda fountain, where all-day breakfast and seasonal pies serve as staples. Key Lime Hibiscus and S’mores Pies are always on deck, and in December, many more join the old reliables: White Chocolate Peppermint Mousse, Brandied Apricot Cheesecake, Cranberry Cherry Crumble, and Butterscotch Cream (with pecan praline, no less). While you’re at it, sample other crowd-pleasing picks, from Sourdough Cinnamon Rolls to Maple Pecan Scones.
Cost: $$
How to order: Pre-order holiday pick-up online.