Kailley Lindman
As Cookie Monster once said, "C is for Cookie". And as we once said, "H is for Here's a list of the 13 best damn cookies in all of Chicago, from a bacon-chocolate chip cookie in Wicker Park to a skillet cookie in Lincoln Park".
Bacon Chocolate Chip Cookie
Mindy’s Hot Chocolate (click here for address and info)Wicker Park
Mindy Segal’s brilliant, meat-flecked creation is the stuff that Jim Gaffigan’s dreams are made of: chocolate chips, homemade cookie dough, chunks of salty, smoky Gunthorp Farms bacon, and the whole thing is cooked in bacon grease. Every bite packs a subtle hit of fatty meat, while maintaining that just-like-Mom-used-to-make-‘em, classic choco chip cookie taste.
Cookie Dough
County BBQ (click here for address and info)University Village
One of our favorite Taylor St BBQ joints sells its house-made, eggless (read: safe to devour) cookie dough by the spoon, and it's loaded with chocolate chips, pecans, and the same guilty satisfaction that comes with sticking your hand/leg into a tub of store-bought Toll House dough.
Triple Chocolate Chunk Cookie
Insomnia Cookies (click here for address and info)Lincoln Park
What makes these Insomnia Cookies good isn't the fact that they have giant chunks of chocolate in them, it's the fact that they have giant chunks of chocolate in them that you can get any time before THREE IN THE MORNING. $12 will get you a box of a dozen triple chocolate chunk cookies. Did we mention they do late-night delivery, too? 'Cause they do.
Ranger Cookie
Sweet Mandy B’s (click here for address and info)Lincoln Park
Not only does Sweet Mandy B's have a fantastic tea party aesthetic, but they've also got some of the best sweets in the city, including confetti cake rice krispie treats, snickerdoodle cupcakes, and size-of-your-head ranger cookies crammed with coconut, oats, and chocolate chips.
Shortbread
Floriole (click here for address and info)Lincoln Park
Located just a couple doors down from Sweet Mandy B’s on Webster, Floriole is a quaint bakery boasting a spectacular array of award-winning breads, pastries, and other delectables. The cookie move, though, is the shortbreads -- they're sweet, buttery, and simple. Plus: if you buy enough, you can play Jenga with them.
Skillet Cookie
Crossing (click here for address and info)Lincoln Park
Crossing’s monster skillet cookie topped with ice cream, whipped cream, chocolate, and caramel sauce is the biggest one you're gonna find on this list. It's awesome for sharing and even awesomer for, um, not sharing.
Coconut Macaroon
Lovely (click here for address and info)West Town, Edgewater
You can either dunk Lovely’s thick, chewy macaroons in a mug of coffee, or spread some Nutella on them... and then dunk them in a mug of coffee. Totally your call.
Peanut Butter Oatmeal Cookies
Leghorn (click here for address and info)Ukrainian Village
Follow up a fried chicken feast with Leghorn's impossibly delicious PB oatmeal numbers, which're smothered in toasty, smoky, burnt sugar Fluff. They're a nostalgic twist on the Fluffernutter sammie -- complete with inevitably sticky fingers -- and are a welcome change from your garden variety chocolate chip cookie.
Bacio di Dama con Nutella
Eataly (click here for address and info)River North
Mario Batali’s Italian food emporium houses one of the greatest man-made creations in River North: a Nutella bar where you can enjoy Nutella muffins, Nutella-filled crepes and croissants, BREAD SMOTHERED IN NUTELLA, and this hazelnut cookie sandwich held together with, yup, Nutella.
Dipped Chocolate Chip Butter Cookie
Dinkel’s (click here for address and info)Lakeview
When you're not stuffing your face full of Dinkel’s awesome donuts, you’ll find yourself stuffing your face with these buttery little numbers. The shortbread-like cookies are studded with mini-chocolate chips, and dipped in your choice of dark or milk chocolate. Since they’re small, Dinkel’s only sells ‘em by the bag. Oh. Darn.
French Macaron
Vanille Patisserie (click here for address and info)Lincoln Park
Vanille’s macaron selection changes around regularly, which makes pinpointing a specific cookie for this deliciously, deliciously challenging. Three sure-things, though, if they've got 'em: chocolate mint, red velvet, and PB & J.
Iced Sugar Cookie
A Baker’s Tale (click here for address and info)Wicker Park
Pull up a seat beneath the faux tree decorated with leaves made of pages from Lewis Carroll’s Alice’s Adventures in Wonderland, and nosh on the expertly crafted iced sugar cookies; they’re firm and chewy, and the almost-too-pretty-to-eat royal icing amps the sugar content up to just the right level.
Brown Sugar Chip
Ferrara Bakery (click here for address and info)University Village
You can’t go wrong with any of the delicious Italian cookies at this bona fide Italian bakery, but the brown sugar chips take the cake (er, cookie?). Thanks to extra butter in the dough, they flatten out in the oven, which means that you’re going to get crunchiness, chewiness, and sweet buttery flavor in every single bite.
Kailley Lindman is a contributing writer for Thrillist Chicago, as well as a food blogger, bacon enthusiast, and devout user of the Oxford comma. Follow her at @KailleysKitchen.
Our Newsletter