I grew up in chicago.
If you want the city or the suburbs, I prefer the city.
Yes Wrigleyville is amazing, along with Lincoln Park, Lakeview, Roscoe Village, Bucktown, North Center, Ravenswood...even more expensive and closer to the Loop (center of chicago/financial district, its called the Loop b/c the El [elevated subway] loops around this area several times] is the Gold Coast, Streeterville, Goose Island, University Park.
All of the above stated is going to have a 20-30 y/o range most in college or post college professionals, TONS of bars and nightlife, Plus you have Cubs and North Avenue Beach...Chicago is just amazing and I hope to be back in that area at some point in my life.
As for the northern Suburbs towards PWK, your looking at much older subdivisions, the North side is the older side of chicago, but great suburbs to live, I grew up in Naperville on the West side (bout 30 min from DT chicago) can't go wrong with either