Asado Coffee Co. Kevin Ashtari roasts his beans in a drum roaster behind the counter daily and rigorously trains his baristas, resulting in toasty, full-bodied cups of coffee. A café con leche and an alfajore (Argentine caramel sandwich cookies made locally by Lucila’s Homemade) make a perfect pair. 1432 W Irving Park Rd (773-661-6530). El: Brown to Irving Park; Red to Sheridan. Bus: 9, 22, 80. Average cup of coffee: $3.
Bake Husband-and-wife Jennifer and Eric Estrella turn out homestyle cookies, cupcakes and pies with a level of expertise that can’t help but show off their seasoned pastry chef backgrounds. In a storefront that’s both kid-friendly and appropriate for adult-age lingerers, those pies are actually stunning galettes made with butter-rich pastry, and that cookie (whether it’s chocolate chip, peanut butter or the mammoth homemade Oreo) is crisp on the outside and soft on the inside. 2246 W North Ave (773-384-7655). El: Blue to Damen. Bus: 49, 56, 72. Average baked good: $4.
Cookie Bar The 18 cookies on display at Cookie Bar start off chewy, with thinnish, caramelized and just barely crispy edges, and get progressively softer as you work your way to the center. This, of course, is exactly how most people want their cookies to be. People also usually prefer good quality chocolate (Cookie Bar uses Callebaut), the occasionally quirky flavor (a chai chocolate chip with warm, spicy undertones) and cookies that don’t cost $4 (here the cookies are about five inches across, and cost $1.25). So guess what, people? Cookie Bar was made for you. 2475 N Lincoln Ave (773-348-0300). El: Brown, Purple (rush hrs), Red to Fullerton. Bus: 8, 11, 74. Average baked good: $1.25.
Fritz Pastry Former Blue Water Grill pastry chef Nathaniel Meads is behind this Lakeview pastry shop, and he’s managed to convince hungry wanderers that there is indeed a reason to look inside the shop’s dreary tinted windows. Incredibly friendly counter help, solid coffee cakes and streusel-topped fruit tarts make nice latte companions, and Meads has built up a following for his endlessly rotating flavors of French macaron cookies. 1408 W Diversey Pkwy (773-857-2989). El: Brown, Purple (rush hrs) to Diversey. Bus: 9, 11, 76. Average baked good: $2.
Hilary’s Cookies Hilary Black is not a vegan. But most of the cookies on display at her simple Lincoln Square shop, the outgrowth of a decadelong cookie business that’s brought her into Whole Foods stores across the region, are. What’s up with that? They’re softer, she says. Turns out that’s true—both the butterscotch and chocolate-chip cookies are so soft and delicious they’re almost like eating cookie dough. Tasty? You know it. Healthy? You can pretend. 4917 N Lincoln Ave (312-285-5055). El: Brown to Western. Bus: 11, 49, 49B, 81. Average cookie: $2.50.
Twisted Baker There’s nothing twisted or off-kilter about this second-story Old Town bakeshop. In fact, the tarts (banana cream, apple pie) and cupcakes (red velvet, carrot cake) are pure, straightforward, old-fashioned goodness. It’s the cookies, though, such as the rustic cornmeal rounds with a hint of lime and buttery shortbread, that are instant classics. 1543 N Wells St (312-932-1128). El: Brown, Purple (rush hrs) to Sedgwick. Bus: 9, 11, 72, 73, 156. Average baked good: $3.