Chicago's Best Viewpoint
Looking northwest from the Adler Planetarium. The view from here is especially beautiful/spectacular/fabulous in the summer months when Monroe Harbor is filled with hundreds of sail boats. Even without the boats, you've got a huge section of Chicago's iconic skyline along Michigan Avenue in the background, and all the beautiful trees and shrubbery of Grant Park in the middle. Calling this view “picturesque” is an understatement! This particular view has been the subject of posters, wall hangings, paintings, and jigsaw puzzles (I had one years ago). It is quite panoramic, extending from the Shedd Aquarium on the southwest all the way to the end of Navy Pier on the northeast. In my opinion, there is no better view from down here on the ground. And it's FREE. (I have a few great photos that I hope to post soon!)
Runners up: The northwest view of the city from the north east end of Navy Pier, which includes the John Hancock building, the “Lookout Point” on the northwest side of the entrance to the Shedd Aquarium, and the south and east sides of the Adler Planetarium. From there on a clear day, you can see all the way across Lake Michigan to the smokestacks on the shores of Indiana!