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Chicago’s Oldest Bakeries Share Their Christmas Cookie Secrets

Some of Chicago's most beloved bakeries have to start making cookies weeks before the holidays because demand is so high. Check out a few of their recipes.

Cookies from Alliance Bakery.
Instagram/Alliance Bakery
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CHICAGO — Some of Chicago’s most beloved bakeries have to start their cookie-making weeks before the holidays begin — demand is just that high.

And though sugar cookies are always a hit and make for fun designs, the city’s sweetest spots are also making hundreds of classic shortbread cookies and unique treats like cucidati.

Three of the oldest bakeries in Chicago told Block Club about the cookies they make for Christmas.

Check out their goodies (and maybe try baking them):

Alliance Bakery, Wicker Park

Alliance Bakery’s shortbread butter cookie is a tried-and-true holiday treat that the beloved spot, 1736 W. Division St., offers year after year.

The recipe’s been in use since 2007, when owner Peter Rios bought the bakery. The cookie is the same as the shortbread offered year-round — but it’s cut into holiday shapes and decorated in unique, bright ways for this time of year.

“We want them all to be works of art,” Rios said. “The cookie itself is already delicious. It’s just a matter of having fun with colors, designs and shapes.”

And Alliance does: During a visit last week, the bakery offered a splashy array of snowman faces with colorful accoutrements, plus Christmas trees, ornaments, reindeer and snowflakes.

Many of those same shapes come back yearly, but Rios said they don’t like to repeat themselves at Alliance — so the decorations, accents and colors change. New shapes and styles are introduced annually, as well. One year, the team put together cookies that looked like sweaters and mittens.

“We couldn’t keep those in stock,” Rios said.

This year, the two best-sellers are the snowman faces and Christmas trees.

Rios said the beauty of Alliance’s holiday cookies is found in the all-natural ingredients and the endless creativity of the bakery’s cookie decorator.

“We like being able to be flexible, create, and not have any restraints,” he said. “You’re never going to find a catalog of designs; it’s always custom. For cookies we put out daily, I give free reign to our cookie decorator. The creative ideas come from her, with input from me. I try not to set boundaries other than make it fun and make it colorful.”

Alliance Bakery’s shortbread butter cookie

Yield: About 48 cookies


  • 450 grams butter
  • 400 grams sugar
  • 2 large eggs
  • 2 tablespoons vanilla extract
  • 710 grams all-purpose flour
  • 1 tablespoon baking powder
  • 1 teaspoon salt


  1. Cream butter with sugar until softened.
  2. Add eggs one at a time to incorporate.
  3. Add vanilla extract.
  4. Mix flour, salt and baking powder in a separate bowl.
  5. Slowly add flour mixture to the butter mixture.
  6. Cool and refrigerate for at least four hours.
  7. Roll out, cut and shape cookies. Bake in an oven at 350 degrees Fahrenheit for 15-20 minutes.

Ferrara Bakery, Little Italy

When Salvatore Ferrara came to the United States from Italy in 1900, he carried with him recipes for old-world cookies and treats. He put them to use when, in 1908, he opened Ferrara Bakery, Chicago’s first Italian pastry shop.

Those recipes are still in use at the bakery at 2210 W. Taylor St. — now owned by Ferrara’s granddaughter, Nella Davy — including holiday favorites filling the cases right now.

“My favorite is the cucidati,” Davy said about a fig-filled Christmas cookie that’s iced and topped with nonpareils. “We used to sell them just at Christmas. Maybe 15 years ago, we decided that at Christmas we sell so many that these people must really like it. So, we’ll sell them all year round. But it’s still a Christmas cookie.”

It’s the most-requested Christmas cookie at the bakery, in fact, with sales spiking during the holiday season.

And though the cucidati are sold all year, many holiday-only treats come out around Christmas. One of them, struffoli, causes a bit of confusion throughout the rest of the year. It’s essentially a Christmas-tree-shaped tower of small, unfilled cream puff balls, stuck together with honey, drizzled with more honey and topped with nonpareils.

“The Sicilian people call it pignolata,” Davy said. “It’s so funny because people will call during the year and ask if we have pignolata, and I say sure, because we make pignolati cookies. The Neapolitan people, though, we call the Christmas trees struffoli. But the Sicilians call the Christmas trees pignolata. Now that we’re so aware of that, we always ask what they’re really looking for if it’s an odd time of year.”

Other holiday favorites at Ferrara include castagnelle (nicknamed tetu), which are spiced dough balls iced in white, green and red sugar. They’re difficult to make, and the recipe is pretty particular, Davy sais, so the bakery only sells them at Christmastime.

Sweets lovers can also find chocolate-covered almonds, cashew bars, traditional Italian cookies and pineapple slices, which are another of Davy’s favorites.

“We put pineapples in a machine like a slow cooker that turns the fruit around and around,” she said. “It cooks for maybe three hours, down to almost nothing. You take that, and you take your dough, and you roll it and slice it, like making it a biscotti. It’s out of this world.”

Roeser’s Bakery, Humboldt Park

If you’re looking for traditional variety in holiday cookies, stop in to Roeser’s Bakery, 3216 W. North Ave. The crew sells about 30 types — almost all of which have been around since the bakery opened in 1911. Each 1-pound box comes with 25 cookies, each a different style.

“The recipes are much older than me,” said owner John Roeser IV. “Probably older than my dad, too.”

Want something with nuts, chocolate, fruit, white chocolate or dark chocolate? How about something soft, crispy or with streusel on top? Roeser’s has you covered.

Currently, the most-requested holiday cookie at the bakery is one shaped like a Christmas tree. They come in two sizes: The small size goes into that 1-pound box, and the large ones are wrapped individually and tied with a bow.

And though Roeser said his favorite holiday cookie at the bakery is an icebox cookie (a basic dough rolled in sugar or nuts, topped with fruit and fondant), he agrees the Christmas tree ones have a certain mystique.

“Some people like to call the baking industry witchcraft,” he said. “There’s something about it. We’re using the same dough and the same sugar that we would use for other cookies, but for some reason on that cookie, it tastes different.”

Roeser and his team get started baking the holiday cookie batch about three weeks before Christmas. This year, he expects they’ll go through at least 350 1-pound boxes of cookies.

“Without our customers and staff, we wouldn’t be here,” Roeser said. “I really appreciate all of them, now more than ever. The holidays are a time to reflect on all the positive things that have happened throughout the year and throughout your life. It’s a time to be grateful.”

Roeser’s Bakery’s chocolate chip cookies

Recipe from “Historic Chicago Bakeries.”


  • 12 ounces sugar
  • 12 ounces brown sugar
  • 1/4 ounce salt
  • 8 ounces butter
  • 8 ounces all-purpose shortening
  • 8 ounces eggs
  • 1/4 ounce vanilla
  • 1 1/2 pounds cake flour
  • 1 1/2 pounds small bittersweet chocolate chips
  • .13 ounce baking soda


  1. On lowest speed with a paddle, cream the sugar, brown sugar, salt, butter and shortening until incorporated and softened. Scrape the bowl. The more you cream these together, the more the cookies will spread because the dough will be softer.
  2. Add the eggs and vanilla slowly. Scrape again after fully incorporated.
  3. Add the flour, chocolate chips and baking soda. Mix only until the flour is fully incorporated into the dough. Do not over mix.
  4. Scoop the cookies onto parchment paper at 1.5 ounces per cookie. Bake at 400 degrees Fahrenheit for 16 minutes or until you see the edges become golden-brown.

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