The 8 Cookies Every Chicagoan with a Sweet Tooth Needs to Try

There’s nothing better than homemade cookies…except, of course, professionally baked cookies at some of the best bakeries around the city. So put down that roller and join the cookie crawl. Here are eight Chicago cookies that will transport you back to childhood.

The Most Iconic Diners Around Chicago

Mindy’s Hot Chocolate

Fudge Thumbprint From Mindy’s Hot Chocolate

These are not your grandma’s thumbprint cookies. The gooey chocolate morsels are made with burned sugar (see: the ones all the way to the right). And they fly off the shelf, which is really saying something considering the other treats offered at this dessert mecca (see: all the other cookies pictured).

1747 N. Damen Ave.; 773-489-1747 or

Vanille Patisserie/Facebook

Macaron From Vanille

With all the pretty pastel colors and exotic flavors—strawberry lemongrass, anyone?—choosing a macaron from Vanille isn’t easy. Save yourself the stress and go for a box of 6, 12, or 24. Tell yourself it’s because you get a better value that way.

Three locations;

Sweet Mandy B’s/Facebook

Cookie Dough Sandwich From Sweet Mandy B’s

In all our years of baking cookies, we can’t believe we never thought of this. Even if you have no qualms eating raw cookie dough on your own, rest assured, Sweet Mandy B’s has made the filling of this next-level sandwich safe to eat (aka eggless).

1208 W. Webster Ave.; 773-244-1174 or

Mary O’Connell/Facebook

Iced Butter Cookies From Al’s Deli

There are good cookies, and then there are those you travel outside the city for. The iced butter cookie from Al’s Deli in Evanston is the latter. Make the most of your trip down the Purple Line by commencing your meal with one of Al’s equally tasty sandwiches on a crunchy baguette.

914 Noyes St.; 847-475-9400 or


Maple Pecan From Floriole

Nutty and crunchy with the sweetness of maple. This cookie is like the perfect fall day—except that you can’t dunk a fall day into your chai latte.

1220 W. Webster Ave.; 773-883-1313 or


Crispy Chocolate Chip From Summer House Santa Monica

Never again choose between a chocolate-chip cookie and a Rice Krispie treat. This slightly salty and super-fudgy cookie is studded with chunks of the classic bar. The whole thing is massive, yet you’ll find yourself refusing to share.

1954 N. Halsted St.; 773-634-4100 or

“Original” Ferrara Bakery/Facebook

Italian Cookies From Ferrara Bakery

We love these cookies because buying in bulk is encouraged. Also, they’re delicious: The pignolati (pine nut) and amaretto (almond paste) are two standouts. The Ferrara family has been churning them out since 1908, so you know they’re tried and true.

2210 W. Taylor St.; 312-666-2200 or

Dinkel’s Bakery/Facebook

Oatmeal Raisin From Dinkel’s

Dinkel’s is known for its doughnuts, but we think the cookies deserve some love. Specifically, the oatmeal raisin, which strikes the perfect balance between soft and chewy. If doughnuts are an acceptable breakfast food, cookies are, too, right?

3329 N. Lincoln Ave.; 773-281-7300 or