I like the oak park area, just outside the city itself to the west but you can easily take the green or blue lines downtown however if you are looking for night life better to live in the city itself the trains are safer downtown becuase there is an area on the west side that isn't great....everything is fine until about 6:30 at night but gets deserted after that. The trains do have cameras but that's not a huge deterrent...of course you can always drive a lot of restaurants have valet parking etc

Anyway you'll get bigger accommodations with cheaper parking outside of the city assuming you have a car....there is also an art league and arts district in oak park.

If you like the city itself wicker park is pretty trendy but you might try river north depending on affordability....Ukrainian village is more affordable but not a ton to do some ethnic restaurants etc. Not sure on current safety on that one, belive its ok.

All in all it will be very different than Kenosha so you might feel more comfy in the burbs or not.....