The John Hancock Center offers a beautiful view over the city of Chicago and Lake Michigan. The best time to be there to get a good shot is probably about sunset and blue hour. There are no tripods allowed at the observation deck, but you can use the heaters at the windows to get a sharp shot or even do a long exposure.
The John Hancock Center is pretty easy to find as one of the highest buildings in Chicago. The best way to get there is probably by subway. The admission currently costs about 18$ and you can enter this building from 9am until 11pm.
Insider trick: If you don't want to pay the admission you can also get up there to a restaurant, which is just below the observation deck. Entrance is free, but if you want to take pictures, the observation deck seems to be the better alternative.
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