First let me say that I have a distinctive sweet tooth, sweet but not too sweet. I also am not the biggest lover of chocolate, goo, or nuts.
Open a bit laterFox and Obel's Apple Pie-- The best that I did not make myself. Have it heated. The crust is amazingly flaky and you can taste the butter. They also have a la mode with Homer's Vanilla Ice Cream, Cafe open until Midnight, seven days a week!
Sweet Mandy B's- Old school Bakery with a place to sit. Lovely red velvet or yellow cake cupcakes, fantastic banana pudding with vanilla wafers that are not soggy! They also have coffee, espresso, hot chocolate, hot cider, and tea. I believe they are open until 10.
Intelligentsia Coffee-- Southport Grocer's cupcakes ( both chocolate and vanilla), Maude's Organic Carrot Cake, Miss Fran's shortbread (depending on which location you can get single pieces either plain or a delightful chocolate chip) and a lovely, not to sweet zucchini bread. Have it with hot cider, coffee, or their nice selection of teas. I think the original in Lakeveiw is open until 10.
Come for dinner and stay for desertLula Cafe- Always seasonal and delish also committed to more than pasta for vegetarians and offerings from small farmers. A few months ago I had a not too sweet generously sized portion of sweet potato pie ( I asked them to hold the marshmallows-- I am a Southerner and a Vegetarian). They used to sell Maude's Organic Carrotcake, but they do their own in house. Last spring or summer I had a fantastic semi-freddo with blood oranges that was one of the most perfect endings I have ever had.
Graham Elliiot- Carrot cake is fantastic, along with Maude's Organic the Best Carrot cake I have ever had!
Green Zebra- Also Sunday Brunch- The Madelines I had a few months ago were amazing. They had a beautiful color, with lightly-browned edges and a moist (cake-like) center. I could eat these by the truckload.
Closing EarlierBittersweet- Lovely environment with table service, but I don't think they are open past 7 pm. I had a fantastic cheesecake last week that included their brownies. I don't even like chocolate and this was magnificent, albeit rich, so a sliver is all I could handle.
Brown Sack- Hopefully heading over there in a few moments. Many adore this place, I don't even love sandwiches and I feel the same. You must have the Vanilla Milkshake. Oh you can taste the butter notes, and no I do not get the whipped cream. I believe the winter hours are Tuesday-Saturday 11 am until 8 pm.
Marcus Samuelson's Burger stand (7th floor of Macy's on State Street)- I did it yesterday. A very close second to the famed Brown Sack Vanilla Milkshake. They also have portions of custard in chocolate, vanilla, or strawberry, just right size.
FoodLife/Sacred Grounds (Water Tower Place)- Lovely marble pound cake. Also a yummy banana pudding with unsoggy wafers among the offerings. Oh yeah, an assortment of gelatos and sorbets.
Ditching Work Early Head to the Lobby at the Peninsula for Afternoon Tea- Weekday service is available. The sweets are also seasonal and generally include a souffle as well. The scones are lightly sweetened and do not require Devonshire cream or a fear of losing your dental work. Other two-bite wonders too numerous to mention, plus they are pretty and the service is lovely.