Chicago’s housing stock is dominated by building types that demand more from painters than a standard suburban job. The city has roughly 60,000 two-flats, thousands of Chicago Common brick greystones, and dense blocks of pre-war bungalows where exterior paint must withstand winters that swing between subzero temperatures and summer humidity near 90 percent. Painting the interior of a two-flat in Cook County runs between $6,000 and $12,000 depending on square footage, while brick exterior work costs between $1.40 and $4.20 per square foot, with older Chicago Common brick buildings frequently requiring repointing before any paint is applied.
Chicago homeowners pay close attention to how painters handle the transition between interior and exterior seasons. Because exterior painting windows in the city are compressed to roughly May through October, scheduling demand peaks early and experienced contractors fill their books quickly. Locals also tend to ask about freeze-thaw compatibility in paint formulations, since products that perform fine in moderate climates can fail on masonry facades that go through extreme thermal cycling year after year.
Lookswell Painting Inc.
Founded: 1963
Address: 1951 W Cortland St, Chicago, IL 60622
Phone: (708) 532-1775
Website: https://lookswell.com
Services: Residential interior and exterior painting, commercial and industrial painting, drywall repair and refinishing, cabinet refacing and restoration
Products Used: Not specified
Lookswell Painting has operated as a family-owned business out of Chicago’s Bucktown neighborhood since 1963, making it one of the longest-continuously-running painting contractors in the city. Now managed by President Jim Scanlan, the company formally incorporated in 1994 while keeping the family-run structure intact. Their two-year workmanship guarantee and decades-long presence in the market give them a level of institutional knowledge about Chicago building types, particularly brick greystones and older two-flats, that newer contractors rarely match.
Painters Inc.
Founded: 2005
Address: 920 N. Ridge Avenue, Suite C-1, Lombard, IL 60148
Phone: (630) 214-9562
Website: https://www.paintersinc.net
Services: Commercial interior and exterior painting, HOA and condo painting, industrial painting, structural steel and precast concrete painting, metal roof painting, floor marking and line striping, fire escape painting, parking garage painting, rust and corrosion control
Products Used: Benjamin Moore, Sherwin-Williams
Painters Inc. operates as a purely commercial contractor, with no residential work in their scope. Their portfolio spans high-rises, hotels, hospitals, office buildings, and parking garages throughout the Chicagoland area. The company is EPA Lead-Safe Certified, OSHA compliant, and holds membership in both the Painting Contractors Association and the Community Associations Institute, reflecting a client base that skews toward property managers and institutional owners rather than individual homeowners. All painters are direct employees, not subcontractors.
Pivot Painters Chicago
Founded: Not specified
Address: Logan Square neighborhood, Chicago, IL (street address not publicly listed)
Phone: (312) 854-9180
Website: https://www.pivotpainters.com
Services: Interior painting, exterior painting, cabinet painting and refinishing, wallpaper removal
Products Used: Not specified
Based in Logan Square, Pivot Painters focuses on the residential interior market across Chicago’s North Side neighborhoods, including Wicker Park, Bucktown, Lakeview, River North, and Andersonville. The company backs all work with a two-year warranty against peeling or blistering, which it applies to both interior and exterior projects. Their cabinet refinishing service has become a frequently requested add-on for owners of Wicker Park and Bucktown greyflats where kitchen updates are common but full cabinet replacement is cost-prohibitive.
Frequently Asked Questions
Q: How much does interior painting cost in Chicago?
A: Interior painting in Chicago typically costs between $2 and $6 per square foot for walls and ceilings. For an average bungalow, a full interior repaint runs between $3,500 and $7,500. Homes in Cook County with more complex layouts, trim work, or wall repairs needed can push total costs to $10,600 or higher. Labor accounts for 80 to 95 percent of most interior painting invoices in the Chicago market.
Q: When is the best time of year to hire a painter for exterior work in Chicago?
A: The reliable exterior painting window in Chicago runs from mid-May through early October, when temperatures stay above 50 degrees Fahrenheit overnight, which is the minimum many paint manufacturers require for proper adhesion and curing. Contractors book up quickly from June onward. Scheduling in May or September tends to get better crew availability and sometimes lower pricing than peak summer months.
Q: Does painting a brick or greystone facade in Chicago require permits?
A: Purely cosmetic repainting of exterior brick or greystone in Chicago does not typically require a permit. However, if the work involves tuckpointing or masonry repair, permits may be required depending on scope. Homeowners in Chicago landmark districts, including parts of Lincoln Square, Wicker Park, and Pullman, should check with the Commission on Chicago Landmarks before making color changes to exterior facades, as some buildings carry review requirements.
Chicago’s painting contractors deal with building conditions that few other markets face regularly: 100-year-old brick facades, basement moisture that wicks through interior walls, and exterior seasons compressed by a climate that punishes shortcuts in surface preparation. The companies that have remained in business here across multiple decades have done so by treating prep work as a discipline rather than a cost to be reduced.