Failing to winterize properties in Chicago can lead to significant risks, including frozen pipes, heating system failures, roof leaks, and drainage issues caused by ice buildup. These problems can result in costly emergency repairs and unsafe living conditions. Multifamily property owners and managers face additional challenges, such as maintaining common areas and ensuring residents are prepared for heating or plumbing emergencies. The guide also warns of potential hazards like carbon monoxide exposure from improperly maintained heating systems and the dangers of snow and ice on exterior surfaces, which can lead to accidents or non-compliance with local ordinances.