I've been to a number of bakeries recently and figured I'd throw out what I found.
I lost the receipt, so I can't remember the name, but there's a small bakery on Pulaski and Waveland run by an older Italian-American gentleman. Not much there - the usual danishes, some cookies, cinnamon bread, a salami/cheese deli area for sandwhiches. Had an almond macaroon which was fine, though old, and a lemon cookie, which wasn't worth finishing. These were the 2 most interesting items to me.
European Classic Bakery on Elston and Bryn Mawr was more promising. A woman whose accent I couldn't identify (Austrian?) came out and answered questions as best she could in broken English about the various cream-based pastries (napoleans, etc.) and cookies. When I asked for a certain cream-layered wafer cookie, she said they were a little old and would give some to me for free.
I tried some of these mini cream pastries (thin wafers filled with various buttercreams), some small cookies and a rum ball. While some of them were old and tasted of refrigerator, the fresher ones were pleasant. The rum ball wasn't impressive. But with such personalized care, I'd go back and try some fresher items.
Cafe Calao is just down the street from the new Miami Sweets ice cream place. The cafe makes their own puerto rican pastries, and offers sandwiches. I came late in the day, but even so enjoyed a cheese-filled pastry and a very nice budin (custard/bread pudding served as a slice) with nice soft raisins soaked in rum, I think. Sandwich menu looked intriguing.
Vanille Patisserie I've commented on before in a search for great croissants. I happened by around 2:30 pm and they had one croissant left, so I had it while talking with the owner. This is still the best croissant I've had in Chicago. Even hours after its baking it was crisp and crunchy on the outside, and delightful in every other way.
I asked the owner how business was doing, since they're not really in a pedestrian area where people would walk by before work or to a train. He said it's been going well, but more people drive up the the Starbucks and Einstein bagel place across the street to pick up coffee and pastry. Arg! If only I lived nearby. They have high end pastries as well, so I can see this as a destination pastry shop for many.
I hope their location works out. Does anyone else remember the small pastry/sorbet place on Broadway and Buckingham (9 years ago?) run by a Yugoslavian husband and wife (their descriptor)? They made superior pastries and fruit sorbets so intense and pure they must have been made with little or no water added. I especially remember the kiwi. They disappeared after about a year and a half, later replaced by an Einstein Bagels. Hopefully Vanille will fare better.
European Classic Bakery
5939 N. Elston, (Elston and Bryn Mawr)
2638 W Division St
2229 W. Clybourn