Book as soon as you know what you need, which usually means late winter, before the weather is warm enough to work. Walk the building at the first thaw, photograph problems and ask for estimates early. We cannot quote you a contractor wait time or a permit time, and we have no verified data on spring demand. What you can control is how ready you are: photos, a scope, and the permit questions answered.
The best time to book an exterior contractor in a Chicago spring is before spring, when you have the problem list and the questions ready, not on the first warm Saturday. We cannot give you a wait time. We have no verified data on contractor demand or on how long any permit takes, and anyone who promises either is guessing. Here is what you can do in the meantime.
Why not wait until it is warm?
Because masonry work has temperature rules. Under the masonry industry's cold weather guidance, "cold" means any temperature below 40 degrees Fahrenheit, and protection steps get stricter as it drops (BIA Technical Note 1). Preservation guidance for repointing puts wall temperatures between 40 and 95 degrees as the safe range for mortar (National Park Service). So the earliest weeks of spring can be too cold for some work, and a good contractor will tell you so. That gap is the time to get inspected, scoped and scheduled. For trade by trade timing, see the best time of year for each exterior repair.
Many owners start looking for a contractor when the first warm weekend arrives, after a winter of noticing small problems. The ones who get a smoother start usually have photos, a short list, and have already asked about permits. That is a pattern we see, not a statistic.
What should you do before you call?
- Walk the building at the first thaw. Use what to check on your Chicago building after winter and take dated photos of everything you flag.
- Rank the list. Water getting in, loose brick, and anything a person could be hurt by come first. Cosmetic work comes last.
- Ask for estimates early. Written, itemized, from licensed contractors. Our questions to ask a contractor and license check cover what to compare.
What permit questions should be settled first?
Ask who pulls the permit. Most small repairs go through the City's Express Permit Program, which replaced the old Easy Permit process in November 2023 (City of Chicago). Masonry such as tuckpointing is on its list of eligible work (City of Chicago). A reroof needs a Chicago-licensed general contractor unless the owner qualifies as owner-contractor, and the roofer must hold an Illinois roofing license (City of Chicago). Scaffolding, dumpsters and materials on the sidewalk, alley or street need a separate permit from CDOT (City of Chicago). Rules and fees change, so confirm current details with the Department of Buildings.
One date to know: the City's Shared Cost Sidewalk Program opened its 2026 applications on January 12 through 311, first come, first served, and you must reapply every year (CDOT). Check the current window on the City's site. If a sidewalk is on your list, that is a winter task.
When should you call us?
If you have a list of exterior problems and want a straight read on what is urgent, our masonry and exterior crew will look at the building and give you a written scope. Call early in the year. The Chicago maintenance calendar shows what to line up each season, and what exterior work happens in winter covers what can start sooner.
Common questions
As soon as you have a scope, which usually means late winter. We have no verified data on contractor wait times or demand, so we will not promise one. Ask each contractor how they schedule and when they could realistically start.
For most masonry, roofing and concrete beyond small exempt repairs, yes. Ask who pulls the permit and get the permit number before work starts. Check requirements and fees with the Department of Buildings, since they change.
Sources
- Brick Industry Association: Technical Note 1: All-Weather Masonry Construction (PDF)
- National Park Service: Preservation Brief 2: Repointing Mortar Joints in Historic Masonry Buildings (PDF)
- City of Chicago, Department of Buildings: Express Permit Program
- City of Chicago: Express Permit Program: Masonry Work
- City of Chicago: Guide to Building Permits: What Types of Work Do Not Require a Building Permit?
- City of Chicago: Express Permit Program: Reroofing
- City of Chicago, Department of Transportation: Shared Cost Sidewalk Program
Facts last checked: October 7, 2026.
This article explains general rules and common situations in Chicago. It is not legal advice, and City rules change. For a specific property, check with the Chicago Department of Buildings or a licensed professional.