Chicago and Oak Park · free referral service

Two-flats, bungalows and a short outdoor season

Chicago exteriors get painted in a window of a few warm months, and interiors keep painters busy the rest of the year. Tell us about your building and independent Chicago painters will contact you.

Illustration of a brick two-flat with freshly painted wood trim
Illustration (AI-generated). Not a real project and not work by any painter we refer.
  1. 1

    Where is the job?

    Your ZIP code or neighborhood.

  2. 2

    What needs paint?

    Apartment and condo turnovers, Porches and back stairs, Bungalow and greystone trim, Frame cottages.

  3. 3

    How should we send it?

    Best Price, Fastest Start or Top Quality.

Painting Quote Request (FJL)

Step 1 of 3 · free estimates · takes about a minute

Step 2 of 3 · Project details for an accurate price

Only property type is required — share what you know.

Have photos? Great — the painter who contacts you can ask for them, or mention them in your notes.

Step 3 of 3 · Where should painters reach you?

Your details only go to the painter(s) matched to your request.

Choosing Best Price? Expect a few calls, texts or emails from local painters.

Before you send a Chicago request

  • Note the year the building was built. In pre-1978 buildings, ask for the firm's EPA lead-safe certificate.
  • For condo buildings, check whether the association controls exterior and common-area colors and schedules.
  • If you rent units, say which are vacant and when. Turnover jobs are easier to price with dates.
  • For porches and stairs, mention any soft or damaged wood. Repairs may need a separate contractor or permit.
  • Ask each painter for proof of insurance and any license the city or your suburb requires for the work.

Choose how many painters see it

Each option sends your Chicago request to a different number of independent painters.

Best Price

Shared with up to 5 painters

Good when you want several quotes to compare and are fine fielding more calls.

Good for repainting a condo or apartment between tenants.

Fastest Start

Sent to 3–5 painters

Good when timing matters more than gathering the widest set of bids.

Good when a lease starts soon or a porch needs work before winter.

Top Quality

Usually goes to 2 painters

Good for detailed or older-home work where you want fewer, deeper conversations.

Good for a greystone or older frame house where prep and lead-safe work matter.

No lead prices are shown here; the request is free for homeowners.

What Chicago owners hire painters for

Apartment and condo turnovers

Walls, ceilings, doors and trim between tenants, a big share of work in a city where most homes are rented.

Porches and back stairs

Wood porches and stairs need regular scraping and coating to stand up to winter.

Bungalow and greystone trim

Wood windows, soffits and cornices on masonry buildings, where the brick or stone itself is usually left bare.

Frame cottages

Older wood-sided houses with many layers of paint, where prep and lead-safe practices drive the price.

Common areas

Hallways and stairwells in multi-unit buildings, often scheduled around residents.

Painter working on a building exterior
Stock photo (Unsplash, Margo Evardson). Not a project by any painter we refer.

Chicago painting questions

When can exteriors be painted in Chicago?

Mostly late spring to early fall, on dry days warm enough for the product.

Is there lead paint in my building?

If it was built before 1978, assume so until tested. Hire an EPA RRP-certified firm.

Can you help with a whole multi-unit building?

Yes. Describe the units and common areas and painters can quote it.

Do I have to paint brick?

Usually not. Most masonry on bungalows and greystones is left unpainted. Painted brick is a different job that needs breathable products and careful prep, so ask painters about it directly.

Can interiors be done in winter?

Yes. Interior work goes on all year, and winter can be easier to schedule because painters are less busy with exteriors.

Do you cover Oak Park?

Yes, along with Chicago neighborhoods across the city.

How many painters will contact me?

Best Price is shared with up to 5 painters, Fastest Start goes to 3–5 and Top Quality usually goes to 2.

paintinginchicago.com is a free referral service, not a painting contractor. Painters who respond are independent businesses; check licensing, insurance and references before you hire. We do not write reviews or rate painters.

Start your free request