I’m planning a trip to Chicago and I’m wondering when is the best time to visit? I’m looking for a time of year that has the best weather, activities, and attractions. I’m interested in seeing some of the city’s famous landmarks, trying out some of the best restaurants, and taking in the culture of the city. I’m also hoping to find some great deals on flights and hotels. Is there a time of year that is better than others for a trip to Chicago?