The view from the Hancock Observatory is probably the best in the city. The observatory itself is kind of weak, and the lines can be long, but you're here for the view anyway, right? For up top, you can sometimes make out Michigan and if it's super super clear, Wisconsin. You get sweeping views of the lake beaches from way up north to around the bend down south. Lake Shore Drive is beautiful up here at night. As is Navy Pier. Plan on about 45 minutes to enjoy it all, plus 15-30 minutes in lines.
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