I see your profile picture is near the water. I imagine that You like water so try the lakefront. Spend a day on the lakefront, aka Chicago's back yard, and see if that feels like an area you can enjoy. Bring your bike or blades so you can cruise around a bit. Think about what activities you enjoy and the answer will come to you.
It really depends on what you are looking for and the type of activities you participate in. Find a broker or leasing agent depending if you are buying or selling. Find someone who understands your needs.
What areas are you referring to? Also, give us a little more information about yourself such as your personality, what you are looking for in a neighborhood, etc. Please feel free to contact me if you want to discuss in detail.