The Chicago Winter Dining Challenge and Prequal’s Innovative Solution

COVID-19 unexpectedly and quickly disrupted everything when it took hold of the United States in the early part of spring 2020. Businesses and their owners were in shock and faced dire consequences if they could not creatively respond to the new and continually changing set of circumstances – the same was brutally real for the restaurant industry.

A warm, dry summer allowed establishments to combat a respiratory virus with open-air outdoor dining. This approach proved successful from both the safety and business perspectives. Yet, in the era of a pandemic, one pivot is never enough. Faced with the reality that COVID-19 was not ready to retreat before the onset of another harsh Chicago winter, the city was confronted with yet another looming challenge for its vast constituency of restaurants to stay financially afloat. The dilemma was stated: “How might we stimulate and encourage safe outdoor dining and entertainment during cold weather in Chicago?” The City of Chicago presented its predicament publicly to crowdsource input and innovation. 

The goal was to spark innovative thinking to uncover a unique solution or solutions that could benefit patrons and business owners.

Contest Description

The contest was open to everyone locally, nationally, and even globally—each proposal needed to be defined and detailed using the design thinking criteria provided.  

Therefore, key design factors were included to help consider, evaluate, and assist in the idea selection process. 

The application included: concept overview, feasibility, technical overview, equity, prototyping, user research, and Covid-19 Safety.  

Typically in these parts of a concept, you will uncover the defining traits that elevate an idea into a solution because they incorporate and consider a human-centered approach.

Additionally, Chicago’s’ Winter Dining Challenge prioritized safety and equity consistent with the Chicago Recovery Task Force Advisory report.

Proposed ideas were divided into three distinct categories: outdoor dining ideas, adjacent indoor ideas, and cultural change.

Prequal’s Idea

Prequal was thrilled to participate and recommend an innovative solution in the cultural change category. Prequal proposed the idea of a Chicago Mealathon with the command to “Bundle Up. Mask On. East Out.” 

The Prequal team included the following summary description in the application:

The alternative-marathon is a fun, community generating campaign focused on supporting restaurants and waitstaff during this disrupted COVID-era in a city with unpredictable weather. Diners sign up for the Chicago Mealathon and commit to eating at least 26(.2) meals out at participating establishments across the city throughout winter.

Race participation options follow a traditional marathon format and includes a race packet and bib number at varying levels with corresponding benefits like masks, cold weather branded merchandise, coupons, and elusive reservations.

Eaters can track their progress through an app to compete for categorical prizes. Meals/points can be earned for takeout & gift card purchases, but users earn more for onsite dining, during bad weather, or for visiting a restaurant in a clearly identified hub.

Race entry fees to be donated to the IRAEF relief fund for food service workers & sponsors to underwrite restaurant participation, including marketing & implementation costs.

Why this is a Strong Idea

Prequal examined the needs of Chicago and its stakeholders (restaurants) through research and empathy mapping and attempted to find the best connection to motivate diners and serve owners. Minimal cost and deployment effort for the city and restaurants and incentives for the customer directed the brainstorming process. 

The resulting idea prompts consumers to dine, even during unpleasant weather conditions.  

The corresponding research provided evidence that consumers/diners would latch onto this community-competition-for-a-mission type of event. 

This solution’s premise also aligned strategically with Chicago’s economic recovery plan, and the restaurants would benefit without the need for additional resources or investment. There are many detailed facets of the concept that bring the idea to life. At its core, it’s a feasible idea with historical evidence of similar success that could be implemented within weeks throughout a city as large as Chicago.


When the evaluation phased of the contest ended, participants had submitted 643 ideas overall. Mayor Lightfoot released a detailed report showcasing “The Top 60 Innovative Designs”. Prequal’s Chicago Winter Mealathon was one of only 13 nominations in the Cultural Change category and placed in the top 10% of ideas overall. You can view the full report here.

It remains to be seen if Chicago will adopt this approach or utilize it as a springboard to launch a similar endeavor. However, a creative idea-driven through design thinking methodology does produce winning results.  And if Chicago isn’t ready to truly embrace this innovation, another city will surely see the vision to move it forward.