Food & Drink

The 13 most drool-inducing cookies in Chicago

Published On 05/20/2014 Published On 05/20/2014
best cookies chicago bakery
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".

Sean Cooley

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.

Kailley Lindman

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.

Kailley Lindman

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.

Sean Cooley


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.

Sean Cooley

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.

Sean Cooley

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)
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.

Baker's Tale

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.

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1. Insomnia Cookies 2260 N Lincoln Ave, Chicago, IL 60657 (Lincoln Park)

Insomnia Cookies has your late night munchies covered. This Lincoln Park cookie shop is open 'til 3am and offers 20+ desserts either frozen or baked (some frozen AND baked). Cookie flavors include triple chocolate chunk, s'mores, peanut butter, and more!

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2. County BBQ 1352 W Taylor St, Chicago, IL 60607 (West Loop)

If you want to explore the wide world of bacon and BBQ, look no further than County BBQ, which has got burnt ends, brisket, and a bacon parfait (!!!).

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3. Crossing 2548 N Southport Ave, Chicago, IL 60614 (Lincoln Park)

A sprawling 6,000sqft sports joint outfitted with 50-plus plasmas and four individual bars -- including one dedicated to their enormous beer garden -- Crossing's the latest effort from the Benchmark folks, serving up Korean steak tacos as well as KU-inspi

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4. Lovely 1130 N Milwaukee Ave, Chicago, IL 60622 (West Town)

This Charming West Town bake shop features coffee, espresso, tea, pastries, sandwiches, and soup, but they're best known for their coconut macaroons, which are best enjoyed via a dunk in a cup of Joe.

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5. Floriole Cafe & Bakery 1220 W Webster, Chicago, IL 60614 (Lincoln Park)

Floriole Café & Bakery’s beginnings were confined to a 10-by-10 tent at Green City Market, where the menu was limited to pastry alone. Today, from its two-story Lincoln Park-based brick and mortar, Floriole continues to sell its French pastries, en masse, but with an expanded inventory. Now, you can enjoy your pastry with coffee, quiche, breads, sandwiches, salads, and more. The levain, canelé, and other French delicacies may rival those actually made in France -- the baker cut her teeth at San Francisco’s acclaimed Tartine Bakery, after all -- and the quiche is served in shells that are like golden-brown butter sculptures, and are not to be missed.

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6. Eataly 43 E Ohio St, Chicago, IL 60611 (River North)

Eataly Chicago is the newest hub from Mario Batali. Head to any of his food shops for authentic grub, or take some classes!

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7. Vanille Patisserie 2108 N Clark St, Chicago, IL 60614 (Lincoln Park)

This authentic French patisserie in the heart of Chicago doles out a wide variety of French pastries, cookies, and other deletable treats. Pro tip: go for one (or seven) of their famous macarons.

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8. Dinkel's Bakery 3329 N Lincoln Ave, Chicago, IL 60657 (Lakeview)

Dinkel's is serving up some insanely delicious baked goods, but be sure to hone in on their donuts and specialized cakes.

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9. Leghorn Chicken 959 N Western Ave, Chicago, IL 60622 (Ukrainian Village)

Leghorn Chicken is one of the best fried-bird establishments in Chitown. Get their chicken-fried fries, or even some free condoms (seriously).

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10. Sweet Mandy B's 1208 W Webster Ave, Chicago, IL 60614 (Lincoln Park)

With delicious confections like cakes that come in flavors that range from Pumpkin to lemon to Snickerdoodle, Mandy B's is your one-stop-shop for sweets in Lincoln Park. Don't miss their stand-out cookie, The Ranger, that's crammed with coconut, oats, and chocolate chips.

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11. Ferrara Bakery 2210 W Taylor St, Chicago, IL 60612 (West Loop)

Ferrara Bakery is a bona fide Italian bakery with delicious cookies, pastries, and specialties like their cannoli cake (a layered cake soaked in rum, layered with fresh stawberries and Italian custard, plus their cannoli cream, and then iced with whipped cream).

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12. A Baker's Tale 2127 W Division St, Chicago, IL 60622

A Baker's Tale is a delectable Division bakery that's doling out some of the most seriously-insane cookies in the whole city. Wait in line for its iced cookie snaps, generously-iced cupcakes, or get a custom cake made for that special occasion you, uh, keep meaning to have an excuse to buy a cake for...?

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13. Mindy's Hot Chocolate 1747 N Damen Ave, Chicago, IL 60647 (Wicker Park)

Pastry chef Mindy Segal's Bucktown restaurant is synonymous with comfort food from both the sweet and savory sides of the spectrum. Open for lunch, dinner, and weekend brunch, Mindy's Hot Chocolate serves soul-warming dishes, like the Slagel Farm beef burger topped with a fried egg, creamy mac & cheese, and daily soups with crusty sourdough bread. Of course, a meal here isn't complete without dessert, which should include an order of the amazingly rich hot chocolate and a slice of the daily cake (or anything off the dessert menu -- it's all addictive).