Top picks: B-grade or better, up to $5,000/mo

23 structures, auto-ranked by composite score — this list updates whenever the underlying data does, no manual curation.

1AI-290Chicago Greyhound Terminal · Near West Side · $4,250–$4,750/mo81

2BUS 145957-5959 · Edgewater · $2,250–$2,750/mo76

3BUS 14West Peterson Avenue · North Park · $2,250–$2,750/mo75

5BOhio StWest Ohio Street · Near North Side · $3,750–$4,250/mo74

7BIL 64North Normandy Avenue · Austin · $4,250–$4,750/mo73

8BIL 64North Normandy Avenue · Austin · $4,250–$4,750/mo73

9BUS 142607 · West Ridge · $2,250–$2,750/mo72

10BUS 142743 · West Ridge · $2,250–$2,750/mo72

11BUS 142717 · West Ridge · $2,250–$2,750/mo72

12BUS 146017 · West Ridge · $2,250–$2,750/mo72

13BUS 145947-5959 · West Ridge · $2,250–$2,750/mo72

14BI-90South Harper Avenue · South Shore · $2,750–$3,250/mo71

16BOhio StWest Ohio Street · Near North Side · $3,750–$4,250/mo71

17BUS 41Phil & Ted's Service · West Ridge · $2,250–$2,750/mo71

18BIL 192121-2125 · North Center · $4,250–$4,750/mo per face3 facesFace 1 · #016-33356 Face 2 · #016-36560 Face 3 · #016-4045571

19BIL 19AT&T · North Center · $4,250–$4,750/mo70

20BI-90East 79th Street · South Shore · $2,750–$3,250/mo70

21BIL 192034 · North Center · $4,250–$4,750/mo70

22BWestern Ave3807 · North Center · $3,750–$4,250/mo70

23BI-908423-8427 · South Chicago · $2,750–$3,250/mo70

Data as of September 2026