Three bids for the same Chicago apartment repaint can differ by thousands of dollars. Here is what each line item should say, and which omissions cost landlords the most.
A property manager in Lakeview sends the same six-unit repaint out to three painters and gets back numbers that range from $9,000 to $22,000. The instinct is to assume someone is padding and someone is honest. Usually neither is true. The bids are describing three different jobs.
Painting is unusual among trades in that the finished product looks nearly identical on day one regardless of how it was done. A wall skim-coated, primed, and given two full coats and a wall given one thin coat over dirty plaster both look fine at the walkthrough. The difference shows up eighteen months later, when one unit still looks sharp for the next tenant and the other needs a full repaint because the paint is burnishing, peeling at the trim, or bleeding old stains through.
That is why the cheapest bid frequently costs the most over a five-year hold. The goal when comparing estimates is not to find the lowest number. It is to force all three bids onto the same scope so the number actually means something.
Prep is where the labor hours live, and it is the first thing a thin bid quietly deletes. A serious estimate spells out what happens before any paint is opened: patching nail holes and cracks, sanding glossy trim so new coats bond, skim-coating damaged areas, scraping loose material, degreasing kitchen walls, caulking gaps at trim and baseboards, and spot-priming stains and patches.
In Chicago's vintage housing stock this matters more than in newer construction. Plaster walls in a Logan Square two-flat or an Andersonville greystone crack seasonally as the building moves through a humid August and a dry, radiator-heated January. Settlement cracks at door corners come back if they are simply painted over rather than opened, filled, and taped. If a bid says only "prep as needed," that phrase is doing an enormous amount of work and none of it is in your favor. Ask what "as needed" covers and get it written down.
"Premium paint" means nothing. A real estimate names the manufacturer, the specific product line, the sheen, and the number of coats per surface — walls, ceilings, trim, doors, and closets are often specified separately because they take different products.
Coat count is the single most common ambiguity. "Two coats" over a fresh primer coat is a genuinely different job from "two coats" that includes the primer as coat one. Over a dark accent wall left behind by a departing tenant in Wicker Park, one finish coat over tinted primer will not bury the color, and you will be looking at a shadow under the hallway light for years.
Watch for the difference between contractor-grade and mid-tier product too. In a high-turnover rental, a washable, scrubbable wall paint in eggshell costs a little more per gallon and buys you an extra turnover cycle before the next repaint. Over a six-unit building that math is not close.
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