
Mention visiting Chicago to people and it will evoke thoughts of the many great attributes of this world class city,great museums, outstanding chefs, the best shopping for 500 miles in every direction and a beautiful skyline. One thing it does not bring to mind is fall foliage. While Chicago will never compare favorably to New England it does have some beautiful fall vistas.
For those with plenty of time and a car the best options are day trips to the rolling hills of Northwestern Illinois and the Galena area or to southern and central Wisconsin which has large expanses of rolling terrain and tree filled forests. Much closer to Chicago but still requiring a car and several hours are the Chicago Botanical Gardens and the Morton Arboretum. The Arboretum is about an hour west of downtown and its 1700 acres contain over 4000 different plant species. Their website keeps an up to date fall color report. The Chicago Botanical Garden has over 100 acres containing more than 13,000 trees.
There are a few good options closer to downtown. The Montrose Bird Sanctuary is not only a great place to see migrating birds, I have seen several different types of hawks, many different flycatchers and warblers as well as the only oriole I have ever seen, but it is also a good place to see the fall colors. Just steps north of Navy Pier is my favorite park in Chicago, Olive Park. It juts out over Ohio Street Beach and offers spectacular skyline views over the water with a back drop of colorful trees. Jackson Park, behind The Museum of Science and Industry is another good spot. If you walk over the short pedestrian bridge and take a quick left it is a 2 minute walk to a small Japanese garden. Another personal favorite spot is Promontory Point. It is a small park which sticks out into the lake just north of the Museum. The trees are nice, but the real show stopper is the spectacular views of the skyscrapers as they seemingly rise out of the lake. If you are lucky you may even get to see the flock of parakeets which frequents the park. Northerly Island has a few good trees, but it is the Illinois prairie grasses and the spectacular city backdrop that make it worth the visit.
One unique way to see a lot of fall colors at one time is to go to the top of the Willis Tower or Hancock Building. They may be in the middle of the urban jungle, but when you can see for 20 miles you get to see a lot of color.