There is a lakefront path that runs the whole length of Chicago just for cyclists and pedestrians. Rent a divvy bike or stroll along the shore for a great view of the city.
Bavette's Bar & Steakhouse
https://bavettessteakhouse.com/
Avec
https://www.avecrestaurant.com/
This New York Times guide for things to do on a long weekend in Chicago has some good sights. Also, it highlights our neighborhood, Andersonville!
Here's a google doc with more ideas for activities and restaurants all over the city.