Chicago is gearing up for fall, marking the start of the annual Tribune Holiday Cookie Contest, now in its 40th year. Dust off your cherished holiday cookie recipe and see if you can be among this year’s winners. Previous contests had professional bakers or Tribune journalists as judges. In honor of past participants, this year’s judges include former winners and finalists.
Erin Traynor, a two-time finalist, reached the baking stage with her almond coffee cookies in 2018 and drunk uncle cookies in 2019. At 57, Traynor grew up surrounded by baking, influenced by her mother and grandmothers. Her grandmother even managed the Fingerhut bakery in Berwyn. Traynor has a preference for butter-based cookies with nuts and fruits. She focuses on traditional holiday treats like gingerbread and sugar cookies, and ‘Orange You Glad It’s Christmas’ cookies mimicking chocolate orange flavors. She expressed excitement for cookies with personal stories and whimsical designs.
Alicia Andry claimed second place in 2017 with sweet potato cookies, inspired by Thanksgiving pie. The 44-year-old South Loop resident runs a pediatric therapy practice and sells cookies. An early cooking influence, her grandmother was a chef and her grandfather a pastry chef. Andry believes holiday cookies connect people and spread happiness. Her preference leans toward soft, chewy cookies where flavor carries more weight than appearance.
In 2017, Serena Daley and her friend Maggie Dring placed third for combining s’mores with Rice Krispies Treats in their cookies. Daley, now 26 and working in the candy industry, values classic cookie recipes with a twist and enjoys cookies that can be prepared quickly. Holiday cookies, according to her, reflect varying cultural and familial recipes. Daley looks for originality and whimsical elements where submitters enjoyed the process, emphasizing that baking memories with friends mean more.
How to Enter
Interested in joining? Submit your recipe, a 200-word explanation of its uniqueness, and a photo through the form on this page. Clearly detail your cookie-making process. Original recipes are essential; entries replicating published works will be disqualified. The contest is open only to residents of Illinois, Lake County in Indiana, and Kenosha County in Wisconsin, aged 13 and over. Previous winners from last year’s contest or food professionals cannot enter. Consult the complete rules at chicagotribune.com/cookiecontestrules.
Deadline
Recipes must be submitted by 11:59 p.m. on Oct. 9. Voting starts Oct. 12, allowing daily votes until Oct. 23. The top 12 voted recipes will be professionally baked for sampling by guest judges. The Tribune food team retains the ‘Joe Gray Save’ privilege to include an additional finalist.
Prizes
First, second, and third place winners receive $250, $150, and $50 respectively. Winners will be announced both online and in print on Dec. 2. For inspiration, review stories about past winners and favorite Chicago cookie guides. Try ‘Holiday Cookies, Second Edition,’ featuring past award-winning recipes.

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