Bombon Cake Gallery Since 2001, Laura Cid-Perea and Luis Perea have been churning out wedding cakes, birthday cakes and—most of all—tres leches cakes (the mocha version is incredible). A fire in 2008 destroyed Bombon’s original 18th Street storefront, but Cid-Perea is still dishing out all of her signature pastries here and at three other Bombon locations. The couple’s tres leches cakes are also served at their taqueria, La Lagartija, so you’re pretty much covered whenever that sugar craving hits. 3748 W 26th St (773-277-8777). Mon–Sat 7am–8pm; Sun 8am–7pm. Average mini cake: $6.
Brown Sugar Bakery Stephanie Hart turns out a number of “down-home delights” at her bakery, many of them smacking of the shop’s eponymous ingredient. Peach cobbler, pineapple upside-down cake and sweet-potato pie, as well as by-the-slice or whole cakes such as caramel, German chocolate and red velvet, are just a sample of Hart’s cavity-producing creations. 328 E 75th St (773-224-6262). Mon–Sat 10am–8pm (closed Sun). Average baked good: $3.
Dinkel’s Baking in the Lakeview neighborhood since 1922, this popular German bakery reliably turns out cinnamon-raisin stollen, German chocolate and butter cookies and its signature “sip’n whisky cake,” a moist Bundt cake made with sour mash whiskey. Another draw is the strudel, which comes in several varieties, such as praline-pecan, cherry-cheese and poppy seed. 3329 N Lincoln Ave (773-281-7300). Tue–Fri 6am–7pm; Sat 6am–5pm; Sun 8am–4pm (closed Mon). Average baked good: $3.
Eggy’s At this diner from the Custom House Tavern crew, the savory stuff is the realm of Zach Millican, and the desserts are the work of Erin Mooney. Both play on diner classics, but it’s Mooney who has the enticement edge: Many of her tall, classic layer cakes (chocolate; coconut) are displayed on the counter, making it very, very difficult not to order a slice at the end of a meal. 333 E Benton Pl, suite 103 (773-234-3449). Breakfast, lunch, dinner. Average slice of cake: $7.
TipsyCake Want a cake shaped like an iPhone? A Rubik’s Cube? A bag of Cheetos? Aussie pastry chef Naomi Levine is your woman, and this sunny bakeshop is her laboratory for monumental fondant-wrapped special-occasion cakes. If you’re still waiting for the moment when you need a cake shaped like a hot dog, TipsyCake also offers a selection of brownies, petit fours and a wonderful confection called a Caramel Slice—a layered bar of chocolate ganache and caramel. 1944 N Damen Ave (773-384-4418). Mon–Sat 11am–8pm; Sun noon–5pm. Average pastry: $3.
Tweet Sure, it’s mostly known for brunch (and rightfully so: You haven’t had a Bloody Mary until you’ve had one here with the corn arepas). But anybody who’s tried one of Tweet’s layer cakes (also served at the bar next door, Big Chicks) knows dessert here is a must. Whether red velvet or yellow cake with chocolate frosting, these cakes taste as if they were baked by a loving mother (or at least a loving den mother—which is exactly what Tweet’s owner, Michelle Fire, is). 5020 N Sheridan Rd (773-728-5511). Breakfast, brunch (Sat, Sun), lunch. Average main course: $10.