Dependent on the weather, fall cleanup typically is performed during the months of October and November to ensure your property looks its best throughout the winter months. Be sure to add this option to your lawn care service contract. Given that Chicago winters are harsh on lawns and plants, it is important to remove all the leaves and debris from your property, helping prevent disease and fungus from developing. All leaves, sticks, paper and debris will be removed from the property. Annuals will be removed and Perennials will be cut back from planting beds.