In moving back to the midwest after my years in the south for college I was really excited to partake in autumn activities. One of the main ones in the areas around Chicago is apple picking throughout September and October. Apple Holler is a massive orchard between Chicago and Milwaukee in Wisconsin that grows all different types of apples that are ripe at different times throughout the fall. It has a huge restaurant and place to have cider and make your own caramel apples. There are also tons of other activities onsite including a corn maze and pumpkin patch. Its a fun day trip from the city for all ages.