Chicago's best holiday cookie contest winner may be a surprise

The annual Chicago Tribune Holiday Cookie Contest has been tradition for 36 years. 

Every year bakers from the Chicago area and Indiana vie for the title of best cookie.  

FOX 32's Sylvia Perez went behind the scenes with the Tribune food editor to see how the process plays out and to find out who the winner of this year's competition is – And, of course, what the cookies taste like.

The holidays wouldn't be the same without the flour, sugar, eggs and ingredients that lead to your favorite cookie. Pretty much everyone loves a cookie, and that's why the Tribune Cookie Contest is such a hit every year. It started in 1986. They decided to stop in 1999, and readers were not happy.


"I think they were wondering if, you know, people still wanted to participate in it, if it was going to be something that would go into the next millennia and people reached out and said, ‘Where are my cookies?’ So they brought it back then the following year," Tribune Food Editor Ariel Cheung said.

The contest is so popular there's even a cookbook with the winning recipes from years past. Chung broke down how the contest works. 

Bakers send in their entries; they had 35 this year. Then readers vote on the recipes they want tested, and it's narrowed down to 12. Then Tribune staff members bake them in their kitchens and bring them in for judging day. 

The third and fourth place cookies were only a 10th of a point apart this year.

"We judge them on a scale of 1 to 10 on originality, taste and appearance," Cheung said.

The third place winner this year was a Decorated Snickerdoodle Sugar Cookie. Second place went to a Marbled Pistachio Almond Cookie. 

First place went to Caroline Crispino for her Chocolate Salted-Caramel Surprise Cookie.

Chicago's best holiday cookie is a Chocolate Salted-Caramel Surprise. 

Besides winning the title of best holiday cookie, there is a cash for the top three winners with first place getting $250.

Crispino's winning recipe can be found below: 

Prep time: 20 minutes, plus 30 minutes to chill

Bake time: 9 minutes

Yield: 44-50 cookies


1 cup sugar

1 cup brown sugar

1 cup unsalted butter, softened (2 sticks)

2 eggs

2 ¼ teaspoon vanilla extract

2 ½ cups all-purpose flour

¾ cup unsweetened cocoa powder

1 teaspoon baking soda

50 Rolos, wrapping removed

½ cup granulated sugar

Kosher salt or flaky Maldron salt to finish at the end


1. Heat oven to 375 degrees Fahrenheit. Line a baking sheet with pan liner or parchment paper.

2. Combine sugars, butter, vanilla and eggs in a bowl. Mix until blended well.

3. Add all dry ingredients separately. Mix well. Then add to wet ingredients. Mix well.

4. Cover bowl or remove dough and wrap with plastic wrap and chill for 25-40 minutes.

5. Remove dough and form golf-ball-sized spheres, approximately 1 tablespoon each.

6. Press unwrapped Rolo into the center of one ball and be sure to cover the Rolo by the dough.

7. Repeat for the rest of the dough balls. (Just barely cover the Rolo with dough, without excessive dough around the candy.)

8. Roll dough balls (with embedded Rolo) through sugar spread out on a plate to coat. Place on baking sheet and press each ball with the bottom of a mug, measuring cup or mason jar to flatten slightly at the center.

9. Sprinkle with kosher or Maldron salt in the center on the flattened part of the cookie.

10. Bake for 9-10 minutes. (If you prefer soft and gooey, check after 8 minutes to see how they look.)

11. Cool on cooling rack for a few minutes then watch the caramel ooze out of the center and enjoy. For extra holiday oomph, roll edges in sugar once more for a snow-like dusting.