Chicago's Best Sweets of 2025: #21-25

Shaw's Crab House raspberry pie

This week we explore the Top 25 Sweets in Chicago. Those marked with an asterisk are new entries since the original list back in 2018.

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(21) Cinnamon rolls at Ann Sather*: A Chicago staple that I'm ashamed to have not included in my 2018 list of Top Chicago Sweets. Breakfast entrees come with two sides and each side of cinnamon rolls comes with two, so conceivably you can have two now and two later. I would know. As for the meal, I tend to go (mostly) savory with the Swedish breakfast sampler.

(22) Earl grey custard and sea salt caramel Japanese soufflé pancakes at Hanabusa Cafe*: Ever have soufflé pancakes? They're airy and lite...and they jiggle. If that weren't enough, at Hanabusa they top the pancakes with something more unique than syrup. The earl grey custard and sea salt caramel wage a delicious battle in my mouth where the winner is always me.

(23) Raspberry pie at Shaw's Crab House*: If jam is the more fruit-forward version of jelly, what is the even more fruit-forward version of jam? Answer: This pie. Just crust and loads and loads of raspberry filling. There's nothing gelatinous about it. I recommend getting a scoop of ice cream on the side to balance out the tartness.

Oreo frosted brownie
from Sweet Mandy B's

(24) Tagalong cake at Defloured (rotating menu)* - This gluten-free bakery features a cake of the week and only offers this one once a year around Girl Scout cookie season, but everything about it is worth the wait. One of my favorite chocolate peanut butter things! Also grab the almond fruit bar, which may not look as fanciful as their other stuff, but gives the Tagalong cake competition, imho.

(25) Oreo frosted brownie from Sweet Mandy B's*: This is a lot of brownie right here. Typically, I buy the Oreo brownie at the Streeterville location, eat about half and go to the movies nearby. Then, once I'm seated, I usually decide saving the second half of the brownie for later was unnecessary bargaining and down the rest of it post haste. Just make sure you have water with you because it is suh-weet.