Chocolate Walnut Cookie at Kingsbury Street Cafe ($3.50)
Cookie dunkers, this is your dream. If you simply can't eat a chocolate chip cookie without a tall glass of milk, you know that some softer cookies fall apart, leaving mushy crumbs in the glass. This version is sturdy enough to stay intact, and the nuts benefit from a milky counterpoint.
Chocolate Chip Cookies at Sweet Miss Givings ($2.30)
How to absolve the twinge of guilt you might feel about inhaling one of these ultra-soft, crumbly pillows? Know that all the profits from Sweet Miss Givings' pastries benefit the formerly homeless and HIV-affected residents of Chicago House. Pair this sugary bite with a strong cup of dark coffee to balance the sweetness of those huge, melting chocolate chunks.
Jalapeno Chocolate Chip Cookie at Cookie Bar ($1.25)
When all your bakery does is bake cookies, you're bound to start experimenting. At the retro-themed Cookie Bar, this means flavors like potato chip and Butterfinger. But for something really unique, try the spicy-sweet combo of jalapeno and chocolate chip. It won't scorch your mouth, but it will tickle your nose a bit.
Ranger Cookie at Sweet Mandy B's ($1.95)
This lumpy cookie wouldn't win any beauty contests, but it doesn't have to. Full of oatmeal, chocolate chips, Rice Krispies, and walnuts, it has a lot more going for it than just symmetrical edges. If you can make it through the throng of strollers at the store's entrance, this is your reward.
Chocolate Oatmeal Cookie at City Provisions ($1.95)
Cleetus Friedman's shop is a lot of things to a lot of people: part deli, part retail grocery, part coffeeshop, part liquor store, and it also happens to be a small bakery. Selection varies, but you're lucky if you can catch one of his chocolate oatmeal cookies, especially early in the morning when they're freshly-baked and soft.