Also, many new visitors mistake the Loop for downtown, but the Loop is really just one part of downtown. Downtown encompasses River North, West Loop and a bunch of adjacent neighborhoods where it's fairly lively. Parts of the Loop can be pretty lively at night too, especially off State St where the theaters are (I just saw Hello Dolly last night).
I mention this because there are many midwestern cities (like St Louis) whose downtowns are completely deserted after 5 which gives rise to safety concerns. Chicago's downtown isn't like that at all. It's still comparatively residential. It's somewhat similar to downtown Toronto in that the core business district clears out after 7 and the surrounding areas become more lively.
Architecture and urbanism generate pedestrian activity, and many midwestern towns are not designed for it, but for people to come from the suburbs and park near their office. You can use zoning to build lively neighborhoods, soulless collections of office buildings, or anything else in between. The many municipalities around St Louis, and their planning, also engineer world-leading levels of segregation, both by race and social class. It's no wonder St Louisians ask each other where they went to high school. The way the metro area is designed, it'd be a miracle if it didn't provide a lot of information.