Chicago is bracing for a weekend of cool and cloudy weather, with Saturday expected to bring overcast skies and cooler temperatures typical for this time of year. CBS News reports that showers are likely to develop later in the day, urging residents and visitors to prepare for a damp evening. The high temperature is forecasted to be in the low 60s, suggesting dressing in layers and carrying rain gear. Sunday's forecast indicates a continuation of cool and cloudy conditions, with possible breaks in the cloud cover, though temperatures will remain similar to Saturday.