I've had the good fortune of living in America's largest cities: New York, Los Angeles, and Chicago. Here are a few of my favorite places in each city:

New York

Taim.
Huckleberry Bar.
Highline Park.
Long Island City.

Los Angeles

Au Lac.
Wasteland.
Hiking.

Chicago

Two food spots.
1 bar.
1 shopping.
1 sight seeing