Kennedy Expy, Near West Side

Randolph is maybe the busiest east-west street that cuts through Chicago's loop. So this means that whatever you're looking for, you can probably find it somewhere along Randolph. But it also means that because it's such a busy street, it's not very pedestrian friendly, and parking can be difficult.

By far my favorite thing on Randolph is Flirty Girl Fitness. It's part bar, part spa, but mostly gym that will kick your butt with risque themed workout classes.