
Adler Planetarium
1300 S DuSable Lake Shore Dr, Chicago, IL 60605
The Adler Planetarium was the first planetarium in the Western Hemisphere when it opened in 1930, and its location on the tip of a peninsula jutting into Lake Michigan gives it the best skyline view in Chicago — a fact that the architects clearly knew, because the building is positioned so that the city rises directly behind you as you enter.

Promontory Point
5491 S DuSable Lake Shore Dr, Kenwood, Chicago, 60637, United States
Promontory Point is a man-made peninsula in Burnham Park that juts into Lake Michigan from the Hyde Park shoreline, and it offers the best skyline panorama in Chicago — a sweeping view north to the Loop and south to the steel mills of Gary, Indiana, with nothing between you and the water but a set of limestone steps that descend directly into the lake.

Willis Tower Skydeck
233 S Wacker Dr, Chicago, IL 60606
Willis Tower — which every Chicagoan over 30 still calls Sears Tower — held the title of tallest building in the world for 25 years after its completion in 1973, and at 1,450 feet it remains the tallest building in Chicago and one of the most recognisable skyscrapers on Earth.
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