How to use this checklist: Print or open on your phone during the walkthrough. Check items only after you have looked—not from the listing description. Chicago stock often hides cost in porches, masonry, combined sewers, and illegal garden units.

Before you go: pull violations and tax status from the resources directory. After you go: update your rehab budget and ARV comps before writing an offer.

Related guides: permits · structural renovation · contractor vetting · official portals

Educational tool only—not an inspection report. Hire licensed inspectors for structural, environmental, and systems issues. Confirm unit legality with city records before underwriting multi-door income.

1. Pre-Purchase & Legal Due Diligence

Before you close. Start with the resources directory for portals.

Check Building Violations Portal (City of Chicago) for open cases. Verify Property Tax Status (Cook County Treasurer) — are taxes sold? Zoning / legal unit count — is that garden unit legal? (zoning guide) Water Certification (Full Payment Certificate) status. Permit strategy sketched (Easy Permit vs plan review). (permit handbook)

2. Structural & Mechanical (The Expensive Stuff)

Chicago winters are harsh. These systems must be solid. See also structural renovation.

Foundation: horizontal cracks or bowing walls (common in brick bungalows). Roof: age and layers. Flat roofs need ongoing maintenance. HVAC: existing ductwork? Radiator boiler operational? Plumbing: lead service line from street; galvanized piping inside. Electrical: service amperage (100A min, 200A preferred); cloth or knob & tube.

3. Exterior & Safety

Curb appeal and code compliance. Curb appeal guide.

Porches: rear wooden porches are a major inspection target. Masonry: tuckpointing. Chicago winters destroy mortar joints. Windows: original wood (lead risk?) vs vinyl replacements. Garage: slab condition and leaning walls.

4. Interior Cosmetic

The finish line. Open-concept layouts if walls move (permits).

Flooring: can original hardwood be refinished? Layout: walls to move for open concept? (permit/architect). Kitchen/Bath: cabinet counts, vanity sizes. Basement height: 7ft+? Underpinning is costly. Contractor shortlist with license checks. (vetting guide)

Scope look good? Plan capital next.

Review financing options, then request terms if you need bridge or rental capital. Leverage and rehab draws are underwritten case by case.

Financing overview Request terms

Chicago Rehab Checklist

1. Pre-Purchase & Legal Due Diligence

2. Structural & Mechanical (The Expensive Stuff)

3. Exterior & Safety

4. Interior Cosmetic

Scope look good? Plan capital next.