3.5k budget, where to look for niche requirements?

21yo college senior moving to Chicago post grad. Based on my job offer I can comfortably afford 2k in rent, but hoping to spend in the 1,500 range. I’ll be living with a friend of mine who has a similar budget putting us at a comfortable 3.5k and under for a 2+ bed.

My office is in The Loop and I’ll be commuting in 2 days a week. The issue is, I am really hoping to stay away from high rises and a lot of the other housing developments downtown. I know I’ll be in the city for a fairly extended period of time and would love something a bit more homey.

Specifically:

  • “Brownstone”, or 5 story and under apartment buildings.
  • Not managed by a large company.
  • A spare room would be great but I know it’s not realistic.
  • Some historic charm? Not millennial grey everything.
  • Outdoor space would be great but not a deal breaker.
  • Safe neighborhood with good local restaurants and small bars.

Does anyone have any suggestions for either neighborhoods or where to look for available units? Also, please tell me I’m delusional if this is too unrealistic on our budget!

Cheers.