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)

Chicago's Best Sweets of 2025: #1-5

Lost Larson spread, left to right: almond croissant,
lingonberry cake, afternoon tea bun, chocolate croissant

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, #16-20, #11-15, and #6-10.)

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(1) Afternoon tea bun at Lost Larson*: Flaky dough rolled into a spiral, covered in granulated earl grey sugar and lemon zest. There is always a slight caramelization on the bottom. It is simple, yet mind-blowing. At Chicago's best bakery, this one stands on top. But, honestly, other pastries there could've made this list, too.

(2) Caramel cake slice at Brown Sugar Bakery*: It's sticky, it's gooey, it's caramel-y. I did not know cake icing could be like this. And the cake itself is moist and delish. Probably the best cake slice I've ever had. I will forever be missing their Navy Pier outpost because I don't get down to E 75th St. all that much.

Black Dog Gelato

(3) Goat cheese cashew caramel gelato at Black Dog Gelato - When I moved away from Chicago for a brief spell, this dessert was the last thing I ate before driving out of the city. A subtly sour goat cheese gelato base, a bitter burnt caramel swirl, and crunchy cashews. What it does to my taste buds is borderline erotic.

(4) Strawberry rhubarb pie at Bang Bang Pie (rotating menu) - I've said it before and I'll say it again: The best slice of pie I have had in my life. Sadly, these fruits are not always in season, but at Bang Bang Pie it's pretty much all incredible.

(5) Ellen from Alliance Bakery - The Ellen is a layered pistachio, white chocolate, and cinnamon mousse dessert. It is delicate, which means you have to pretend to be eating it daintily while you shovel it in your face.

Chicago's Best Sweets of 2025: #6-10

Valrhona chocolate iced doughnut at Firecakes

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, #16-20, and #11-15.)

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(6) Bread pudding at Bar Roma*: Tart cherries and dark chocolate always go well together; in an expertly prepared bread pudding they are pure bliss. Top it with salted caramel and *mwah* chef's kiss. (I recommend getting the vanilla gelato on the side.) Side note: Bar Roma is my wife and I's favorite date spot. Don't miss their cacio e pepe.

(7) Valrhona chocolate iced doughnut at Firecakes: Without a doubt the best chocolate icing I've ever had on a doughnut. It's definitely icing textured, but it tastes like a bite of fine chocolate. And Firecakes' yeast doughnuts are where it's at, whether this classic or their more creative flavors that rotate in and out, like dulce de leche and strawberry mascarpone.

(8) Iced housemade chai with ube syrup at Del Sur Bakery*: There is no shortage of items with complexity to their flavor at Del Sur, but the best example may be their chai. Their website notes that the chai contains "clove, ginger, black pepper, cayenne, star anise, cardamom, rose water, and orange." I added some of their housemade ube syrup. I have had numerous ube beverages; this one was the truth.

Spacca Napoli

(9) Panna cotta at Spacca Napoli: If you close your eyes, you might think you are eating the silkiest vanilla gelato ever, punctuated by fruit and a balsamic drizzle. This jiggly Italian custard delivers. An elegant ending after eating the best Neapolitan-style pizza in Chicago.

(10) Earl grey swirl ice cream at Bartleby's* (rotating menu): This was a seasonal fall flavor almost a year ago and I dream of it still. The swirl was a tart raspberry, adding a punch to the warm flavor of the earl grey ice cream base. I'm also a big fan of their honeycomb crunch and my wife always brings home a pint of their dairy-free chocolate ice cream.

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.

Chicago's Best Sweets of 2025: #16-20

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.)

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(16) Purple velvet cupcake at Jennivee’s Bakery: As I've said before, while purple velvet is also available as an airy cake slice, the dense cupcake is the better choice for this particular flavor. While ube can sometimes be a delicate flavor, as a cake frosting, it packs more punch. The denseness of the cupcake helps bring the flavor back down to earth.

(17) Tiramisu at "Original" Ferrara Bakery: Everyone has their preference of what component of their tiramisu should be front and center. Is it the espresso? The chocolate? The ladyfingers? For me, it's the custard, offset by the cocoa dusting on top. And that is why this is the perfect tiramisu. One of several tasty items at Ferrara.

(18) Pecan caramel crisp popcorn from Garrett Popcorn: I defy any dessert-loving omnivore to pass by a Garrett Popcorn without salivating; they pump the intoxicating scent of melted butter and sugar out into the street in front of their stores, making such resistance an impossibility. Most Chicago popcorn fans will point you toward the cheese and caramel popcorn mixture, but I say hold the cheese and add pecans.

(19) Death by chocolate sundae at Vaca's Creamery*: Vaca's offers delectable vegan soft serve in chocolate, vanilla, or twist with homemade vegan toppings based on nostalgic treats. Death by chocolate has chocolate shell--their version of magic shell--and brownie bites. Gobs of chocolate here. They also offer two additional soft serve flavors of the month along with pints of other flavors featuring mix-ins.

(20) Chilled drinking chocolate from Katherine Anne Confections*: A perennial favorite for me at the Andersonville farmer's market, Katherine Anne is best known for the chocolates and caramels. The chilled drinking chocolate features some salted caramel, homemade whipped cream, and cocoa nibs for texture. Simply divine.

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.