There’s something about chocolate chip cookies that gets everyone feeling a little nostalgic. While a simple cookie by nature, there are so many twists and variations that can take this dessert to the next level. Chicago has an amazing cookie culture, with bakery owners and pastry chefs who pull out all the stops. We’ve scoured the city for some of the best chocolate chip cookies. It was both fun and extremely filling. Nevertheless, we’re pretty confident that after tasting some of these, you’ll never go store-bought again.
Nutella Stuffed Chocolate Chip Cookie from Warm Belly Bakery
A simple sugar cookie is elevated to the next level after it’s stuffed to the brim with Nutella and chocolate chips. Topped with pretzel salt, the cookie packs the ultimate sweet-salty punch.
1148 W Monroe St., Chicago & 2472 N. Clark St., Chicago
Chocolate Dipped Butter Cookie from Dinkel’s Bakery
What makes chocolate chip cookies even better? The answer is simple: butter, butter and more butter! The extra butter in these cookies makes them moist and tender, and the flavor profile is enhanced when hand-dipped in melted milk or dark chocolate.
3329 N. Lincoln Ave., Chicago
Chocolate Chip Pan Cookie from Mindy’s Hot Chocolate
Pastry Chef Mindy Segal takes the skillet cookie concept to the next level in this one-of-a-kind creation that starts with a brown sugar chocolate chip cookie. It is finished with coffee cocoa nib ice cream and a warm chocolate fudge drizzle. Mindy knows a thing or two about cookie: she’s the author of the book, “Cookie Love: More Than 60 Recipes and Techniques for Turning the Ordinary Into the Extraordinary.”
1747 N. Damen Ave., Chicago
Double Doozie Chocolate Chip Cookie from Sweet Mandy B’s
The thing about Sweet Mandy B’s is that their signature buttercream frosting is so good, it’s hard to order something on the menu that isn’t frosted. But lucky for us, the shop got the hint and started putting buttercream in everything, and we’re totally smitten with their Double Doozie Chocolate Chip Cookie. It’s not just one, but two chocolate chip cookies held together by buttercream frosting. If that isn’t to die for, we don’t know what is.
1208 W. Webster Ave., Chicago
Rice Crispy Chocolate Chip Cookie from Summer House Santa Monica
Each bite is full of more flavor and texture than the next. But what makes this bakery best seller extra special is the sticky, crunchy and perfectly baked brown butter rice crispy squares sitting on top of this enormous cookie. Eat them first, save them for last or put together the perfect bite—there’s no wrong way to devour this one.
1954 N. Halsted Street, Chicago
Soft Batch Chocolate Chip Cookie from Orland Park Bakery
These cookies are straightforward without any bells and whistles—that’s what makes them so special. Simply baked to perfection and big and rich with flavor and texture, these soft, melt-in-your-mouth cookies are loaded with chocolate chips, ensuring you’ve got the perfect blend in every bite. Simply put, they are unexpectedly delicious.
14850 S. LaGrange Rd., Orland Park
Chocolate Chip Cookie Ice Cream Sandwich from Scofflaw
A gin-fused cocktail bar isn’t where you’d expect to find a delicious variation of a chocolate chip cookie, but this Logan Square spot is an exception. The idea came after Scofflaw developed a cult following for handing out warm chocolate chip cookies to patrons at midnight. Now on the menu and even better with house-made ice cream in ever-changing seasonal flavors, you’ll get the cold sensation of the ice cream when it’s placed between the warm cookies.
3201 W. Armitage Ave., Chicago
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