By: Coop Daley By: Coop Daley | November 23, 2021 | Food & Drink
Pies. Love them or—well, love them, they’re one of the best desserts in the world and are often enjoyed by many during the holiday season, but they're a great any time of year.
As families gather around the dinner table to enjoy a sweet treat, there’s a lot of stress to get just the right flavor: do you go for a sweet apple, or stick with classic of pumpkin? Or do you go absolutely crazy and try something new and fresh?
Regardless, it can be difficult to make such a pie yourself. As a result, we took a look at some of the best places to pick up a slice in Chicago, ranging from delicious originals to updated classics made for all audiences. Hungry? Good, let’s begin.
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1618 W Chicago Ave., West Town / Website
There’s no denying the grip this family business has had on the Chicago area over the past few years. Hossier Mama Pie Company consistently tops lists and rankings, and garners hundreds of five-star reviews online. The pie is, as their name suggests, just as good as mama used to make. While the shop offers plenty of staples—apple, pumpkin and other delicious treats—there’s also the option of several cream and chocolate pies. The menu changes each day, as the business tries to offer different pies for a variety of flavors, and there is no common consensus for what pie is best: some say coconut cream, others say the cherry, a few are chocolate die-hards. Whichever you choose, this is sure to be a hit following dinner.
2051 N California Ave., Logan Square / Website
While most shops on this list are known for fantastic dessert, Bang Bang elevates the pie with sweet and savory options. Customers of the restaurant have high recommendations for a wide variety of dishes, including the S’mores pie, tomato and cheese pie, chicken pot pie and blueberry pie; all of which can be enjoyed in one afternoon. Offering both meals and desserts, this is a wonderful place for takeout and dine-in. Just be sure to come hungry!
5357 N Ashland Ave., Andersonville / Website
This location near the North Side is known for a wide variety of pies, as well as the ability to buy individual slices—a good choice for the picky eaters in all of us. In addition to offering staples like apple and cherry, First Slice is also known for various cheesecakes including pumpkin, blueberry and others. It's worth the drive to Andersonville, as the customer service is sublime and the meals offered are a perfect getaway. Pro tip: try the strawberry rhubarb. You might not find a better option anywhere.
1477 W Balmoral Ave., Andersonville / Website
Technically this is more of a bakery than a pie shop, but anytime someone manages to make a gluten-free option that can match the delicious original, it deserves a place in the list. Defloured is extremely well-regarded for those with dietary restrictions, including gluten and vegan options. As for the pies, you've got to try the oatmeal cream, strawberry rhubarb, apple and cherry. Be advised: these pies must be ordered a week in advance, just so they have time to finish the order. According to reviews online, however, it’s more than worth the wait.
See also: How to Make Vegan Pumpkin Bread and Pumpkin Spice Lattes According to Take Two
3720 N Lincoln Ave., Irving Park / Website
Just off the Brown Line, this bakery is a socially-conscious non-profit that continuously works to provide jobs for the homeless and at-risk youth. The pies are doing lots of good too, as Blue Sky fans rave about the delicious flavors and fruit mixes, all unique by other bakery’s standards. They must be ordered in advance and picked up between 8 a.m. and 2 p.m., but the options of apple cranberry, chocolate peanut butter, dark chocolate pecan and more are well worth the effort. What combo will you try from Blue Sky?
2933 N Broadway Ave., Lake View / Website
One of the many dynamic duos to grace Chicagoland, this list focuses on the latter’s contributions. The pies offered stretch from traditional dessert staples to dinner options for those seeking a larger meal. To start with the dessert, Pie Man brings everything from classic pumpkin spice and blueberry to delicious combos such as pineapple and mango, as well as chocolate pecan and coconut. Dinner options include classics like steak and Guinness to pot pies and other mixes. The crown jewel just might be the mac and cheese pies, each offering a splash of protein. Try the three cheese, barbecue pork and lobster. Oh, and the empanadas are good, too.
6155 N Broadway Ave., Chicago / Website
Part of the Beard and Belly cafe, which specializes in burgers and brunch, this sidebar bakery has plenty to offer for itself. Like others on the list, Honeypie operates with a daily rotating menu, sometimes boasting more than 30 fruit and 50 cream pies on tap. What you can order depends on the day you arrive, unless you order more than 48 hours in advance. Customers can't get enough of the Key Lime pie, a tropical favorite that’s sure to warp you to your favorite beach even in the freezing Chicago winter; as well as the coffee cream pie. Of course, they offer all the originals as well, but where’s the fun in that?
820 W Randolph St., Fulton Market / Website
Another location, another cafe sidebar, another bakery known for pies as well as other things. The cupcakes with ingredients like ice cream, watermelon, pumpkin latte and Cheez-Its are worth a visit, but we're talking pies. Sugargoat has plenty of pies to choose from, with some interesting and perhaps a bit weird options to water your tastebuds. The chocolate french fry pie, cookies and cream, and apple gjetost described as "an apple pie, with a cheesy caramel twist” are especially noteworthy. For the less adventurous, there’s also the usual pecan and citrus meringue, as well as staples infused with a twist. What is pumpkin crunch? Try it for yourself!
Photography by: Brooke Lark / Unsplash
