Chicago's Best Sweets of 2025 - Full List

This week we explore the Top 25 Sweets in Chicago. Those marked wth an asterisk are new entries since the original list back in 2018. (Jump to the full reviews of #21-25, #21-25, #16-20, #11-15, #6-10, and #1-5.)

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It's been a great week exploring the top sweets in Chicago. Click the links above for longer write-ups and tips. Here's the full list:

(1) Afternoon tea bun at Lost Larson*

(2) Caramel cake slice at Brown Sugar Bakery*

(3) Goat cheese cashew caramel gelato at Black Dog Gelato

(4) Strawberry rhubarb pie at Bang Bang Pie (rotating menu)
(5) Ellen from Alliance Bakery

(6) Bread pudding at Bar Roma*

(7) Valrhona chocolate iced doughnut at Firecakes

(8) Iced housemade chai with ube syrup at Del Sur Bakery*

(9) Panna cotta at Spacca Napoli

(10) Earl grey swirl ice cream at Bartleby's* (rotating menu)

(11) Vanilla sour cream doughnut at Downstate Donuts*

(12) Sour cream dutch apple pie at Hoosier Mama Pie Company (rotating menu)

(13) Cookie dough peanut butter milkshake at Chicago Diner

(14) Authentic drinking chocolate at XOCO

(15) Lemon-raspberry brioche French toast at M. Henry

(16) Purple velvet cupcake at Jennivee’s Bakery

(17) Tiramisu at "Original" Ferrera Bakery

(18) Pecan caramel crisp popcorn from Garrett Popcorn

(19) Death by chocolate sundae at Vaca's Creamery*

(20) Chilled drinking chocolate from Katherine Anne Confections*

(21) Cinnamon rolls at Ann Sather*

(22) Earl grey custard and sea salt caramel Japanese soufflé pancakes at Hanabusa Cafe*

(23) Raspberry pie at Shaw's Crab House*

(24) Tagalong cake at Defloured (rotating menu)

(25) Oreo frosted brownie from Sweet Mandy B's*

Honorable mention: Pretty much anything from Mindy's Bakery*

Gone, but not forgotten: Chai-infused French toast from Orange (R.I.P.)

Favorite non-Chicago dessert spot in Chicago: Jeni's Ice Creams (nationwide, originally from Columbus, OH)