Chicago's Best Sweets of 2025: #11-15

Downstate Donuts spread

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. (Jump to the full reviews of #21-25 and #16-20.)

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(11) Vanilla sour cream doughnut at Downstate Donuts*: My absolute favorite donut from Downstate Donuts is the strawberry rosé, but it's a rare find. The good news is it's only a hair better than this, their most classic doughnut. Downstate incorporates potatoes into their dough, making their cake doughnuts standouts regardless of the glaze/topping. This vanilla sour cream glaze adds a tang to the experience.

(12) Sour cream dutch apple pie at Hoosier Mama Pie Company (rotating menu): As I've said before, Hoosier Mama is the queen of the custard pies in Chicago...but her sour cream fruit pies are even better. I've also had the sour cream blackberry, which would rank equally high on this list. The dutch apple one is just a titch better in my opinion.

(13) Cookie dough peanut butter milkshake at Chicago Diner: The best milkshake in the city is vegan. From the makers of the famous veggie Reuben sandwich comes a perfect milkshake that tastes like peanut butter cookie dough if it had been named by Yoda. Did I mention it's vegan? It's vegan.

Xoco

(14) Authentic drinking chocolate at XOCO: From Chicago chef Rick Bayliss, this spot offers tasty tortas, ho hum churros and, the best of the bunch, Mexican drinking chocolate. They offer it in classic or Aztec, which has a spicy kick to it. Which is better? Honestly, depends on one's mood. You can't lose.

(15) Lemon-raspberry brioche French toast at M. Henry: I take all of my out-of-town guests to M. Henry. Usually when I go to brunch, I like to split with a friend, so we can get half savory and half sweet. At M. Henry splitting isn't necessary because the morning sugar high of downing all the French toast is well worth it.