Chicago's Best Sweets - Full List

This week we explore the Top 25 Sweets in Chicago. (Jump to the full reviews of #21-25, #16-20, #11-15, #6-10, #1-5.)

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1.) Strawberry Rhubarb pie at Bang Bang Pie (seasonal)
2.) Ellen from Alliance Bakery
3.) Cioccolato at Osteria Langhe (rotating menu)
4.) Goat Cheese Cashew Caramel gelato at Black Dog Gelato
5.) Strawberry Mascarpone doughnut at Firecakes (seasonal)
6.) Apple Pie at Chopping Block (only at Apple Fest)
7.) Sour Cream Dutch Apple pie at Hoosier Mama Pie Company (rotating menu)
8.) Chai-infused French Toast at Orange (pictured above)
9.) Cookie Dough Peanut Butter milkshake at Chicago Diner
10.) Tagalong cake at Defloured (seasonal)
11.) Panna cotta at Spacca Napoli
12.) Chocolate chip cookie at Publican Quality Meats
13.) Authentic drinking chocolate at XOCO
14.) Stuffed French Toast at M. Henry
15.) Almondolas from Amy's Candy Bar (seasonal)
16.) Katie Cakes at Taste of Heaven
17.) Purple Velvet Cupcake at Jennivee’s Bakery
18.) Pumpkin cupcake at Molly's Cupcakes (seasonal)
19.) Tiramisu at "Original" Ferrera Bakery
20.) Pecan caramel corn from Garrett Popcorn

21.) Cheese and Honey gelato from Frio Gelato 

22.) Cherry pie from First Slice Pie Cafe 

23.) Strawberry Milk Shake at Allende

24.) Mango Italian ice at Miko’s Italian Ice (closed during the winter)

25.) Coconut bao at Wow Bao

Chicago's Best Sweets #1-5

This week we explore the Top 25 Sweets in Chicago. (Jump to #21-25, #16-20, #11-15, #6-10.)

• • •

1.) Strawberry Rhubarb pie at Bang Bang Pie
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.

2.) 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.

3.) Cioccolato at Osteria Langhe
Their menus change, but look for it if you go. The dinner I had there was my favorite ever in Chicago, though again the menu changes. All I can say is that while I ate this I understood chocolate in a new way.

4.) 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. The things it does to my taste buds is borderline erotic.

5.) Strawberry Mascarpone doughnut at Firecakes
As I've said before, my second favorite doughnut of all time. This one is seasonal, though, so if you go when it's out of season, grab the Valrhona Chocolate Glazed yeast doughnut.

Chicago's Best Sweets #6-10

This week we explore the Top 25 Sweets in Chicago. (Jump to #21-25, #16-20, #11-15, #1-5.)

• • •

6.) Apple Pie at Chopping Block
Don't tell my dad this, but this is the best apple pie I have ever eaten. Only available one weekend a year at Lincoln Square's AppleFest.

7.) Sour Cream Dutch Apple pie at Hoosier Mama Pie Company 
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. This one it just a titch better in my opinion.

8.) Chai-infused French Toast at Orange (pictured above)
I've blogged about this before, but I still believe it puts other French toasts to shame.

9.) 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. Did I mention it's vegan? It's vegan.

10.) Tagalong cake at Defloured
The best slice of cake I have eaten in my life...and it's from a gluten-free bakery! Defloured features a Cake of the Week and only offers this one once a year around Girl Scout season, but everything about it is worth the wait.

Chicago's Best Sweets #11-15

This week we explore the Top 25 Sweets in Chicago. (Jump to #21-25, #16-20, #6-10, #1-5.)

• • •

11.) 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.

12.) Chocolate chip cookie at Publican Quality Meats
This cookie is the best cookie I've had that wasn't made by a family member.

13.) Authentic drinking chocolate at XOCO
From Chicago chef Rick Bayliss, this spot offers tortas, churros and, the best of the bunch, Mexican drinking chocolate. Mexican drinking chocolate hot chocolate.

14.) Stuffed 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 is worth it.

15.) Almondolas from Amy's Candy Bar
These are chocolate hazelnut paste-covered almonds. They are seasonal, because Amy likes to play with our hearts. Either that or because she also injects some elf magic into them.

Chicago's Best Sweets #16-20

This week we explore the Top 25 Sweets in Chicago. (Jump to #21-25, #11-15, #6-10, #1-5.)

• • •

16.) Katie Cakes at Taste of Heaven
Buttermilk pancakes, triple berry compote, whipped cream, lemon streusel crumb topping. The challenge, if you choose to accept it, is for the majority of bites to contain a little bit of all four components. Taste of Heaven also serves up a variety of cakes, including the Katie Cakes-like Jeanine's Cake.

17.) Purple Velvet Cupcake at Jennivee’s Bakery
From an earlier post: Also available as a cake slice, the dense cupcake is the better choice. If you've never had ube before, this is an excellent place to start. It's a delicate flavor knocked up a few notches into something truly unique to the Chicago dessert scene.

18.) Pumpkin cupcake at Molly's Cupcakes
I've written about Molly's before. What I might not have said is that, come fall, this is the best pumpkin option to be found in the city. Good luck savoring it. Or go up for a second to really get that autumnal spirit going.

19.) Tiramisu at "Original" Ferrera Bakery
I've blogged about this before. Everyone has their preference of what component of their tiramisu should be in the forefront. Is it the espresso? The chocolate? The ladyfingers? For me, it's the custard, offset by the cocoa dusting on top. To me, this is the perfect tiramisu.

20.) Pecan caramel corn 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 will point you toward the cheese and caramel corn mixture, but I point you toward the pecan.

Chicago's Best Sweets #21-25

 

This week we explore the Top 25 Sweets in Chicago. (Jump to #16-20, #11-15, #6-10, #1-5.)

• • •

21.) Cheese and Honey gelato from Frio Gelato 

This Evanston store opened a second location just south of the Music Box. Most people are lining up outside of Jeni's, but you can beat the crowds with this local option's Argentine ice cream. Don't know what that means? The Cheese and Honey flavor is the place to start.

22.) Cherry pie from First Slice Pie Cafe 

I've blogged about First Slice before, naming its Blueberry Cheesecake as the standout dish. And it is one of the standouts. But time has made me realize how irreplaceable a slice of their cherry pie is. More fresh, tart cherries; less gelatinous sauce.

23.) Strawberry Milk Shake at Allende

Not a milkshake in the sense most people would expect, this thin drink contains no ice cream. Indeed, it is milk, sugar and the flavor of choice. And I'm here to tell you the flavor of choice should always be strawberry. I treat myself to one anytime I go to Victory Gardens' Biograph Theatre or to my favorite music venue in town, Lincoln Hall.

24.) Mango Italian ice at Miko’s Italian Ice

Decisions are tough at Miko's. I could just as easily have named their blueberry or coconut Italian ice as my top pick. But mango is perhaps the perfect Italian ice flavor: sweet with a slight tang, meaty but it goes down smooth. Only open during the summer season. Stop by anytime you pass Damen on the 606.

25.) Coconut bao at Wow Bao

This local chain (from Lettuce Entertain You) is my main go-to for fast-casual when I'm in the Loop. It's a nice, inexpensive local option amongst the chains. But don't skip dessert: warm coconut custard in a doughy bao.