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.)

• • •

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.)

• • •

(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: #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.)

• • •

(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.)

• • •

(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.

• • •

 

(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.

Carina's Cupcakery in Chicago

(Editor's note from 2025: Carina's Cupcakery shut down business on February 1, 2025. Just six months previous, Carina made the cakes for my wife and me's wedding celebration in Chicago. Gone, but not forgotten.)

• • •

A little over a year ago, a theatre artist friend posted that one of his theatre artist friends had started a cupcake business out of her home kitchen. I investigated, saw that she delivered (which has been so necessary in pandemic-land), and dove in, sweet tooth first. Her business, Carina's Cupcakery, may primarily be cupcakes and cakes, but she does many other things, too; over time she has delivered cake pops, caramel corn, and macarons along with my cupcake orders. (These additional items haven't made it to her website's menu yet, but I can attest to their quality for when they do!) 

Carina's specialty is flavors of the Philippines, some flavors I'd first been introduced to by another Jennivee's Bakery and others I first had from Carina. Another menu often features monthly specialty flavors, which means there's often something new I haven't tried on the menu. I've tried the ones I am most excited about and decided it was time to blog about it.

Without further ado, here is my personal ranking from favorite to not-my-favorite-but-still-tasty:

• 

  From Carina's Cupcakery's
  Facebook page.

  Date Night (chocolate covered strawberry, seasonal)
• Ube Jammin' (ube)
• Philippine Sun (mango pineapple)
• Ginger Spice (cinnamon and spices, seasonal)
• Chocolate Cravings (quadruple chocolate)
• Lemonade Stand (raspberry lemonade, seasonal)
• Spill the Tea (chai spices, seasonal)
• Cupcake de Coco (brown sugar and coconut)
• CocoJoy (coconut almond chocolate)
• Cupcakes 'n Cream (Oreo)
• Big Buko (pandan and coconut)
• So Corny (corn and coconut)

If you're like me, you'll try them and soon want to make your way through the menu. It's dangerous, but worth it. So if you're in Chicago, give Carina's Cupcakery a try!

Lost Larson in Chicago

If there's one reason to retcon my Best of Chicago Sweets List, it is Lost Larson. The bakery has become my favorite in Chicago. It's located in Andersonville between two of the neighborhood's longest Swedish holdouts--the Swedish Bakery and the delicatessen--before both tragically disappeared in the past five years. But while Lost Larson is definitely modern, it still keeps things Swedish, offering a lingonberry almond cake, limpa bread and semla, among others delicacies. In addition to their chai latte (the best I've ever had) and their cheddar and kale scone, these are my favorite items from Lost Larson:

(1) Afternoon Tea Bun - To the naked eye, it is a cinnamon roll shape that's merely covered in granulated sugar. Incorrect. There is sugar, lemon zest and earl grey. It is simple, yet mind-blowing. My favorite by far.

(2) Cinnamon Roll Bread Pudding - Like everything at Lost Larson, the cinnamon rolls are good. The cinnamon roll bread pudding, however, is great. Dense and sweet. It may not have a cream cheese frosting, but it doesn't need it.

Afternoon Tea Bun.

(3) any seasonal fruit dough-y pastry - Croissant, danish, whatever they're calling it that day, get it. My favorite is when they have rhubarb, but that is more personal preference than studious recommendation.

(4) Chocolate Passionfruit Caramel Tart - Did I mention they do pastry of the non-dough variety? Lost Larson excels at this, too! What would you say to a dark chocolate tart topped with a caramel that has been flavored with passion fruit? You would say, "Yes. I would like to eat that now, please."

(5) Almond Croissant - Almond croissants were perfected in my mind by West Seattle's Bakery Nouveau. Here at Lost Larson, we have a worthy local option. The almond paste in the middle of this powdered sugar topped delight doesn't taste like marzipan and it doesn't taste like amaretto; it tastes like--who'da thunk?--almonds.

Downstate Donuts in Chicago, IL

Many of us Chicagoans have been craving the foods we cannot access easily during quarantine due to them being outside walking distance. Imagine my delight when a friend spread the gospel of a new doughnut place that delivers! The purveyor in question is Downstate Donuts, where the doughnuts are made with potatoes. Indeed when the half dozens have arrived at my door, they smelled like potato chips. They didn't taste like potato chips, but there's no denying that smell.

As the weeks continue to pass in quarantine, I've allowed myself to make more than one order to this wonderful establishment and create a list of their donuts, from my favorite to my least favorite. Don't get me wrong, though: all of them are good!

L-to-R: Wild Blueberry, Strawberry Rosé,
Lemon Mascarpone, Vanilla Sour Cream

Strawberry Rosé - My favorite of their offerings, they actually boast that this is their first savory doughnut...but it tastes sweet to me! The strawberry glaze is the best I've encountered.

L.R.P. (Lemon Ricotta Pistachio) - Hot on the tail of the previous doughnut, the layered combination gets better with each bite.

Vanilla Sour Cream - Don't bypass this one just because it sounds simple. This classic is classic for a reason.

Sweet Potato Maple - A delightful balance of sweet potato and maple, I actually prefer this version to their other option Maple Pecan, which has too much going on flavor-wise in my humble opinion.

Lemon Mascarpone - As you have probably deduced by now, in addition to having a variety of glazes, Downstate Donuts also uses different doughs. This particular doughnut is decadent and rich.

Italian Cream Cake - I ate the whole thing, but I'm still not totally clear on what was going on with it. All I know is that it was good. The website says the cake doughnut has coconut milk in it!

L-to-R: Vanilla Sour Cream, L.R.P.,
Chocolate Sea Salt, Brown Butter Chai

Wild Blueberry - The glaze has more than a hint of lemon in it, which sadly overpowers the blueberry, even though there are hunks of blueberries in the doughnut.

Brown Butter Chai - I expected more of a punch of flavor than I got in this doughnut, but when has cinnamon on a glazed doughnut ever been bad?

Chocolate Sea Salt - More salt than I prefer on this tasty chocolate glaze. I feel it necessary to reiterate that while this is near the bottom of the list, it still was good!

Salted Peanut Butter - This was the only doughnut of theirs that didn't taste unique to me. I feel I can grab something similar at other doughnut spots.

Delivery from Downstate Donuts is available on Saturday mornings only, so get your orders in before 5pm on Friday this week.

Chicago's Best Sweets of 2018 - 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.)

• • •

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 milkshake 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 of 2018: #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 of 2018: #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 of 2018: #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 of 2018: #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.

Chicago Cake: Molly's Cupcakes

On my dessert hierarchy, cakes are usually way, way down near the bottom, above desserts I dislike (Turkish Delight, banana anything) and below those I do like. But Chicago has taught me what cake and cupcakes are capable of being.

• • •

During the cupcake bubble, I thought I'd tried it all, cupcake after meh cupcake. Then Molly's Cupcakes opened my eyes. All of their cupcakes are worthwhile, so I'll have to limit myself to the Top 5:

1.) Pumpkin Spice - spice cake filled with pumpkin mascarpone, topped with cream cheese buttercream 

An annual favorite during pumpkin season, this cupcake stands tall amongst many would-be competitors for Chicago's pumpkin crown.

2.) Chocolate Raspberry - chocolate cake filled with fresh raspberry puree, topped with chocolate ganache and a fresh raspberry

Raspberry puree is borderline erotic in this dessert. And the chocolate is rich enough to warrant adding the tart raspberry to cut through.

3.) Ron Bennington - chocolate cake with peanut butter filling, chocolate ganache and crushed butterscotch topping

Decadence, thy name is Ron Bennington. Well, maybe not THE Ron Bennington, but the cupcake for certain.

4.) Peach Cobbler - vanilla cake with a peach filling, whipped topping and peach on top

Buttery, sweet and fruity. Just like a cobbler, but lighter.

5.) Red Velvet with Cream Cheese Frosting
Pulling from Molly's selection of make-your-own non-filled cupcakes is a standard so good you're reminded of why it's a classic.

Though they've expanded to New York City and Iowa City, Molly's was founded in Chicago, where it has two locations.

Chicago Cake: Jennivee's Bakery

On my dessert hierarchy, cakes are usually way, way down near the bottom, above desserts I dislike (Turkish Delight, banana anything) and below those I do like. But Chicago has taught me what cake is capable of being.

• • •

From the first time I visited Jennivee's Bakery, I quickly became a regular, trying as many flavors I could keep up with. Their main focus are cakes (which may be light, but are loaded) and cupcakes (which are dense with tasty toppings). A shop in their first year, they do a lot to stick out among the crowd. First, there's the shop's founder, a young Filipino transwoman entrepreneur. Then there's the shop's hours, which cater to the late night crowd. And, best of all, there's the originality of the product, highlighting my three favorites:

Purple Velvet Cupcake - Also available as a cake slice, the dense cupcake is the better choice. If you've never had ube before--a purple yam that features in some Filipino desserts--this is an excellent place to start: ube cake with ube mousse and coconut strings. It's a delicate flavor knocked up a few notches into something truly unique to the Chicago dessert scene.

Sans Rival Cake - As the French name implies, this cake has "no rival." Unlike anything I've had before, this crispy, chewy cake consists of layers of meringue cookies packed between layers of buttercream. I ate half of it (a reasonable amount), telling myself to save the rest for later, but the second half only lasted an hour's break from eating the first...which I suppose does classify as "later."

Mango Mousse Cake - Triple mango! Mango cake with mango cream and bits of mango. Also available as a cupcake, the lightness of cake is better suited to this particular flavor. But don't take my word for it; try both!

Gone But Not Forgotten: Endgrain in Chicago

While going through old blog posts, I happened upon a draft of a post about Endgrain, a restaurant opened by the man some credited with launching the doughnut craze in Chicago. Endgrain was my obsession for a while, even if inconvenient for carless Chicagoans not on the Brown Line. I was saddened a couple years ago when it shuttered.

Endgrain founder Enoch Simpson was more than serious; he wanted people to give doughnuts the respect they deserve. Simpson talked the talk in a Guide to Doughnut Tasting, which, excepting the two bizarre and confusing opening sentences, offers some doughy insight into Chicago's grease-gone-gourmet obsession. Simpson also walked the walk, making the best overall textured doughnut menu in the city.

At the start, there were a mere four doughnut options for customers to choose from: the Butterscotch Bacon—their one constant—and three rotating selections. On most days, there was a jelly doughnut, a chocolate doughnut and a traditional doughnut with a unique glaze, what my waitress called a "vanilla doughnut" and what I'm calling a "rogue doughnut."

The Doughscuit.

After some time, Simpson decided that, rather than jumping on the cronut bandwagon, he’d make his own doughnut hybrid: the Doughscuit, a doughnut-come-biscuit filled with crème frache. It was buttery, sweet and creamy. This was followed by an alternative takes on his creation, including the German Chocolate Doughscuit. The original Doughscuit would go on to win the FirstAnnual DonutFest in Chicago, though I personally preferred the German Chocolate variety.

Despite the Doughscuit’s accolades, I always felt the crown jewel at Simpson’s Endgrain were the jelly doughnuts, which I wrote about in my review of the best of Chicago doughnuts. Put simply, it was the perfect jelly doughnut. And now, sadly, it is gone. My second favorite doughnut at Endgrain was the Butterscotch Bacon, a rare beacon of light in the bacon-doughnut craze. Their version had a gooey butterscotch coating, topped with crispy bacon. In my visits, I also tried Mochanut, Blackberry Peppercorn, Peaches 'n Cream, Nutella Milkstout, Chocolate Turtle and Salted Caramel.



Endgrain, you are gone, but not forgotten!

Chicago Pie: TL;DR

(l-r) Hoosier Mama's Vanilla Cream with Strawberries,
First Slice's storefront, Bang Bang's Blue-barb

As a lover of pie and annual host of a Pi(e) Day party, I often seek out the best bakers of round pastry. In my own city, there is no lack of notable stops. I wrote a series on Chicago Pie's Big Three. Here's the TL;DR.

• • •

Hoosier Mama

Best pies: Dutch Sour Cream [any fruit] and Earl Grey Custard
Biggest overall strength: Custard pies
Extra credit: Best in Chicago at savory pies

First Slice

Best pies: Michigan Cherry and Pecan
Biggest overall strength: Cheesecakes
Extra credit: Gluten free Polka Dot pie

Bang Bang Pie & Biscuits

Best pies: Strawberry-Rhubarb and Chocolate
Biggest overall strength: Fruit pies
Extra credit: Biscuit with toppings


Honorable mention:
Chopping Block

Best Pie: Apple pie
Biggest overall weakness: Only available at Apple Fest and for order at Thanksgiving

Chicago Pie: Bang Bang Pie & Biscuits

Chocolate Pecan and Blue-barb.

As a lover of pie and annual host of a Pi(e) Day party, I often seek out the best bakers of round pastry. In my own city, there is no lack of notable stops. Last year, I began a series covering the wonder that is Chicago pie, starting with Hoosier Mama and First Slice. Here’s the last of the Big Three.

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If asked which of Chicago Pie’s Big Three is my favorite, I’ll likely say Bang Bang Pie & Biscuits. Unlike the other two, I can always rely on something I haven’t tried yet from their rotating monthly menu of six pies, plus weekend specials. Why else might that be? Well...

Bang Bang’s Strawberry Rhubarb pie is the best slice of pie I’ve ever had. Ever. That is no small statement. Usually when I have Strawberry Rhubarb pie, I wonder why anyone would ever want to dilute the tang of rhubarb with the strawberry sweetness. Strawberries may be the perfect food, but rhubarb is a delicacy that one shouldn’t take for granted. But Bang Bang has created a pie in which both superior fruits shine brightly, the tang and the sweetness, neither diluted, both combining their forces into a Super Pie, the likes of which has never been seen before by man or beast. Let us thank our lucky stars for being born in the same time as this pie.

Example menu. It changes.

In general, I feel the main distinction Bang Bang has from its peers is its fruit pies. They use a flaky crust with lard in it, the best of their different crusts. It is glorious. Additionally, they tend to add a little somethin’, somethin’ to their fruit pies, like a drizzle of crème fraiche (as with the Strawberry-Rhubarb) or a lemon crumble topping (as with the Blue-barb pie…that’s blueberry-rhubarb). These extra touches make their already superior product stand out even more.

Bang Bang also does a good job on their chocolate pies. The Chocolate was a favorite when it was featured. It was dark chocolate pastry cream, chocolate french silk, whipped cream, chocolate cookie crust. A more oft-featured menu item is their Chocolate Pecan Pie, which is heavy on the pecans and has none of that overrated sweet jelly stuff. What they have instead is a dense maple sorghum filling, plus a chocolate chip or two in each bite.

Brisket biscuit.

Predictably, the biscuits that make up part of the business name are the best part of the savory menu, offered with a variety of toppings (candied bacon, collard greens, etc.) to turn a side item into its own feast. Bang Bang does offer two savory pies, but they are a bit of a let down; the buffalo chicken pie is really the exact same thing as the chicken pot pie, but with bleu cheese and hot sauce on top. But these are minor slights next to the rest of the menu.

Bang Bang may be my favorite in Chicago pie, but be sure to try Hoosier Mama and First Slice for yourself to decide which is your favorite.

Ferrara Bakery's Pastries in Chicago, IL

At Ferrara's, you can't lose.

In operation since 1908*, Ferrara Bakery is one of the few lingering family-owned Italian eateries on Taylor Street, the road to Chicago's "Little Italy." According to their website, they were actually the first pastry shop in the neighborhood! (The same family also went on to found the Ferrara Pan Candy Company, makers of Lemonheads, Red Hots and Atomic Fireballs, among other candies.) Since I've been finding myself in the neighborhood a lot, I've gotten around to tasting some most of their pastries. Here are my top ten:

(1) Tiramisu - The question isn't whether the tiramisu is the best thing at Ferrara's; the question is whether or not theirs is the perfect tiramisu. The dusting of cocoa powder neither overpowers, nor is overpowered by the espresso. The ladyfingers are a springy vessel that neither steals too much focus nor soaks in too much of the main event. And, blessedly, the predominant flavor is the layers of whipped mascarpone which is airy, but never light on flavor. With the balance of flavors in their tiramisu, Ferrara's has accomplished a rare feat, one worth trying for yourself.

(2) Eclair - From the rich chocolate topping to the the eggy pastry shell to the generous amount of custard within, this is an eclair as it is meant to be. Somewhat delicate, somewhat sturdy and all delicious. These remind me of my mom's cream puffs she made at Christmas, only better. (Don't tell Mom!)

(3) Sfogliatella - My favorite pastry from my 4 weeks spent in Italy and a rare find in America. Sometimes called a lobster tail, these pastries should have a little snap to their crust, but mostly be chewy inside. (A bad sfogliatelle is crunchy throughout. Just say no!) They are also filled with a thick custard (thickened by corn starch, maybe?) that is subtly sweet. At Ferrera's, the sweetness comes from the hints of citrus in the custard and the powdered sugar they sprinkle on top. It is a genuine taste of Italy for the curious. Molto bene! 

(4) Monachine - Take a biscuit--think cobbler topping, not something heavily seasoned and translucent with butter--then stuff it full of cannoli cream. Make sure the cannoli cream has a few chocolate chips in it. Then keep adding cannoli cream until it's overflowing. Add a maraschino cherry and you have a monachine. Sacrilege, I know, but even though it's basically a different take on the cannoli, I like it better than Ferrara's cannoli. 

Sfogliatelle.

(5) Limoncello Cake - This ever-so-slightly boozy dessert is a light layered cake with limoncello (or limoncello flavoring) used to add a citrusy punch. Mostly good, but one or two bites come on a bit too strong along the way...or maybe I just ate it too fast. 

(6) Ricotta Cheesecake - Cheesecake is usually heavy, but there's something even heavier about using ricotta. Fresh ricotta, though, offers a moist quality that makes each bite feel like a sip of water along the way. Order it and your gut will grow three sizes that day.

(7) Custard Chocolate Horn - Similar to the eclair in structure, but with a different shell. This shell is flakier, yet it crumbles more. Eating this pastry is more labor-intensive, even if the rewards are high. I highly prefer the eclair shell to this one.

(8) Cassata al Forno - A dense layered cake containing cannoli cream. Heavier than it looks, but no trouble to finish on my own. This would make a fine birthday cake with the right ice cream, maybe a small scoop of raspberry. Or maybe just raspberries. It's a good cake and flavor, but would benefit from something punching it up a little. 

(9) Cannoli - It's good, but something is off about the cream. A great cannoli offers a wave of different flavors, while Ferrara's offers only two: the shell and the cream. Still good, like I said, but it isn't even the best cannoli on Taylor Street. 

(10) Pasticiotto - Like a tiny pie crust filled with a thick, lemony custard. The lemon flavor is strong here. The texture of the crust is unlike any other Italian pastry I've eaten. Tasty and fun to try, but not one I'll likely revisit anytime soon.

There ya have it! Ten Italian pastries to choose from next time you find yourself on Taylor Street. Buon appetito! 


 * The infamous year the Cubs last won the World Series...OH, WAIT. THEY WON IN 2016. WORLD CHAMPIONS!

Chicago Pie: Hoosier Mama Pie Company

Vanilla Cream with Strawberries

As a lover of pie and annual host of a Pi(e) Day party, my travels often include a stop to see the different bakers of round pastry. But in my own city, there is no lack of notable spots: Bang Bang, First Slice and this one. In this series, I will cover the wonder that is Chicago pie.

• • •

Hoosier Mama Pie Company, how do I love thee? Let me count the ways. First off, there's your name: a clever and functional pun, celebrating both female entrepreneurship and boasting Indiana roots in the ever-competitive Chicago. Second, there is your charismatic owner/chef, who is a winner at all speaking engagements and authored the Hoosier Mama Book of Pie. Third...actually, counting off by number is already a little tiresome. Onward!

Boasting the largest pie menu, both savory and sweet, one could argue that their biggest contribution to the Chicago pie community is their savory pies. While I've never been disappointed with the meal portion of my visits to Hoosier Mama, I feel the Pork, Apple and Sage offers the biggest revelation to the taste buds. (Meanwhile, First Slice offers zero savory pies and Bang Bang Pie Shop offers two versions of the same savory pie.) The savory pies may not actually be the best part of the Hoosier Mama experience, but they are so good that one could argue it's a tie race.

Over on the sweet side of the menu, one can find fruit pies a-plenty, cream pies, chess pies, custard pies and, for the gluttonous indecisive, there is the Pie Flight, three half slices so you can catch 'em all. You'll be safe ordering based on your personal preferences at Hoosier Mama, but in my opinion is they are masters of both the cream and custard pie. My personal favorite are their sour cream Dutch fruit pies with Sour Cream Dutch Apple Pie leading the bunch. Second place goes to the Coconut Cream, tied with whichever custard pie I am currently consuming, be it the Horchata Pie (exclusive to Dove's Luncheonette) or the Ginger Custard Pie.

The only downside of Hoosier Mama Pie Company is also one of their greatest strengths: their rotating menu. Sure, you can't always find your favorite on the menu, but happily you can almost always try something new, whether their pie of the week, a new recipe or one from the recipe vault.

Stay tuned for the final installment of Chicago Pie Week!