Chicago

Chicago's residential real estate market is mid-sized by national standards, about 1.2 million housing units in the city proper, with another 2 million across Cook County's surrounding municipalities. Three structural features distinguish Chicago practice from the broader Illinois framework: a meaningful local transfer-tax stack, a property-tax appeals industry built on Cook County's idiosyncratic assessment system, and a high-rise condo segment that's substantial but architecturally varied.

The closing process is attorney-customary statewide in Illinois, but in Chicago specifically the attorney's role is well-formalized. Buyer and seller each retain attorneys at typical $500–$1,500 fees, with attorney modifications negotiated in the days following offer acceptance. The closing itself happens at the title company's office, with attorneys, agents, lender representative, and title company representative present.

Chicago's transfer-tax stack

The transfer-tax structure in Chicago is layered and split:

On a $400,000 Chicago sale: state + county = ~$600 (seller); city = $4,200 split as $3,000 (buyer) + $1,200 (seller); seller's total transfer tax ~$1,800; buyer's total transfer tax ~$3,000. The buyer's share is unusual, most cities don't split the local transfer tax this way.

There's also been ongoing political debate about a graduated city transfer tax for affordable-housing funding ("Bring Chicago Home") that would raise rates on higher-value transactions. The specific rates have moved through ballot measures and city council action; the rate at the moment of any specific transaction should be confirmed.

Cook County property tax dynamics

Cook County reassesses on a triennial cycle, every property gets reassessed once every three years, with the city of Chicago, the north suburbs, and the south suburbs each on a different year of the cycle. When a property's reassessment year arrives, the new assessed value can shift dramatically from the prior cycle, producing a step change in the tax bill.

The Cook County Assessor's office handles initial assessments; the Board of Review handles first-level appeals. Appeals are common, roughly a third of properties file an appeal in any given assessment cycle, often producing meaningful reductions. There's a substantial cottage industry of property-tax-appeal attorneys and consultants, typically working on contingency fees (a percentage of the first year's tax savings).

The homestead exemption for primary residences in Cook County reduces the equalized assessed value by $10,000, with additional exemptions for seniors (longtime occupant exemption, senior assessment freeze for qualifying low-income seniors), persons with disabilities, and veterans. Applications go through the assessor; deadlines vary.

What buyers should know

The standard Illinois residential purchase contract uses the attorney modification period (typically 5–10 business days after offer acceptance) during which both attorneys negotiate non-price terms. Inspection contingencies typically run 5–10 business days. Earnest money is held by the listing brokerage or buyer's brokerage in trust.

For high-rise condos, the HOA fee can be substantial, $400–$1,500/month is typical, depending on building amenities and reserves. New buyers should request the most recent reserve study and the past 12 months of board meeting minutes to assess the building's financial health and any pending special assessments. Buildings with insufficient reserves and pending major repairs are common in mid-century high-rises.

What sellers should know

Sellers face the symmetric portion of the transfer-tax stack. Required disclosures include the Illinois Residential Real Property Disclosure (covering known material defects, environmental conditions, HOA matters) and lead-based paint disclosure for pre-1978 homes.

Illinois state cap-gains tax is a flat 4.95%. Sellers with significant appreciation pay federal LTCG + 4.95% Illinois + NIIT (for high earners), combined effective rates around 24%–32% on the taxable portion above the federal § 121 exclusion.

How closings work

Chicago closings happen at the title company's office, typically 1–3 hours, with both attorneys, both agents, the lender representative (in financed deals), and the title company representative present. The deed records at the Cook County Recorder of Deeds (now the Cook County Clerk's office, post-2020 consolidation), the various transfer-tax forms get filed, and the transaction completes.

For property-tax appeals (a common follow-up activity for new owners), the Board of Review process is separate from the closing and typically run by specialist attorneys. The state guide for Illinois covers the broader Illinois framework.