The image OP posted is older and zoomed in a bit too much.

If you use Google Earth and use historical aerial imagery, you can see that the bridge is designed as a sperm.

The park where the "head" used to be has been demolished and re-designed.

The pinecone is obvious. It's named the Pritzker Pavilion. Illinois just elected a Pritzker to Governor.

If you go south in Grant Park, you'll see architectural elements more akin to European palace grounds rather than an American city.