Chicago is one of the last major U.S. markets where the rental math can still genuinely work — but only if you underwrite the things that make this city different. The Investing Primer is our field guide: the strategies, the benchmarks, and the Chicago-specific risks that decide whether a deal performs.
It's written from the contractor's side of the table. We renovate these buildings for a living and invest here ourselves, so the rehab numbers in this guide are the ones we actually see — not national averages.
Strategy Deep-Dives
Buy & Hold, BRRRR, and Fix & Flip — when each works in Chicago, and when it doesn't.
2026 Chicago Benchmarks
Current cap rate, rent, and cost benchmarks by property class.
A Worked BRRRR Example
A real-numbers walkthrough from purchase through refinance.
The Risk Chapter
Cook County reassessment, RLTO compliance, insurance trends, and pre-1980 building CapEx — the four risks that sink Chicago deals.
A Taste of the Benchmarks
Three numbers from inside the primer, current to mid-2026: Class B/C two-to-four-unit buildings on the South Side and south suburbs are trading at cap rates in the 7–9% range while north-side equivalents sit closer to 5–6%; a workable BRRRR in this market targets 75% LTV refinance recovering 90%+ of capital; and the underwriting line most investors miss is Cook County reassessment risk — the primer’s risk chapter shows how to model it before you buy. Run any specific deal through the Deal Analyzer to see these benchmarks applied live.
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