Even though wicker park is slowing dying from the infestation of bros and mainstreamers , it's still one of the best places to be in Chicago! There's a lot of great places to go out to like Debonair, Evil Olive and Danny's. I also have a hookah bar that I recommend called arabic cafe. check it.
Boystown is a no brainer. In the summer time all the rainbow flags are out and there's so many pride fests it's insane. It's also a great neighborhood to either just shop in or go out to at night. Can't miss The Berlin and Hydrate if you wanna see a bunch of pretty boys.
My last favorite spot is Logan Square. It's kinda weird cause it's a mixture of mexicans and hipsters. I love all the old houses that are around. Some good place here are the whirlaway and Burlington.