I’ve found that you can see some gorgrous views of Chicago from around the south rim of Lake Michigan. And it’s amazing how far you can see when there’s nothing abstructing your view. For example, New Buffalo, MI is roughly 40 miles (as the crow flies) to Chicago but you can still barely see the tops of a few buildings of the Chicago skyline from the beach at New Buffalo. Take a look at these ten images I found of photos from various distances along the lake. Please note that some of these photos are zoomed in at different levels which means that the skyline may look a little larger in some photos. Also, the map above will give you an overhead visual of where these photos were taken.
New Buffalo, MI (40 miles from skyline)
Michigan City, IN (33 miles from skyline)
Beverly Shores, IN (30 miles from skyline)
Indiana Dunes, IN (28 miles from skyline)
Burns Harbor, IN (26 miles from skyline)
Gary, IN (21 miles from skyline)
Whiting, IN (15 miles from skyline)
Rainbow Park, IL (8 miles from skyline)
Harold Washington Park, IL (6 miles from skyline)
31st St Harbor, IL (2 miles from skyline)