Things to do, places to go
It's been said that Chicago's Neighborhood Parks is one of the 10 parks that changed America. In the late 19C, the two designers Frederick Law Olmsted and Calvert Vaux executed that vision in a system of smaller neighborhood parks that serve better for immigrants and working-class people in Chicago.
Downtown Chicago is beautiful — but once you take the stairs to go down to the ground, you see the completely different landscape of underground space of the city. There are hidden restaurants and bars & clubs, and it's quite fun for urban adventurers.
It's quite interesting to learn how Chicago sold one of its skyways to the private sector. Chicago sold the Chicago Skyway for $1.8 billion
Curbed Chicago has great maps to get the gist of the city.
This essay depicts a personal sense of place in a beautiful and delicate manner, and it's about Chicago.
Where I’m (Not) From Becoming and un-becoming in a city that defies definition
Overall, I think these videos are the best introduction for urbanists;_[Chicago's Geography Advantage](https://www.youtube.com/watch?v=JyuZi9fHC4Y) by City Beautiful_
Chicago and St. Louis Compared by Mr. Beat