22. South Shore Cultural Center
Location: 7059 South South Shore Dr.
A former country club and now official Chicago Landmark (since 2004), the building has been around over 100 years. The opulent site once housed ballrooms, a golf course, and horse stables, and now offers arts and recreational programs like including cooking, yoga, dance, and ceramics classes. That's basically a well-rounded man curriculum, and also a great way to put you close proximity to ladies that will notice your newfound well-roundedness while you take note of theirs. (Sorry, we can't shut off that part of our brain.)