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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Permits are one of the most avoided topics in Chicago real estate investing. Many investors spend their entire careers trying to work around the system instead of through it. In this episode, Tom Shallcross breaks down why embracing the permitting process, rather than avoiding it, actually makes you a better investor and protects your downside long term.
This conversation walks through the permitting process from start to finish, from deciding when permits are required, to working with architects, navigating zoning, inspections, and understanding where investors most commonly get burned.
Episode Summary
Tom explains the Chicago permitting process in practical terms, using real projects and mistakes as examples. He walks through when permits are required, why cutting corners creates long-term risk, how to choose the right architect, and what timelines investors should realistically expect.
The episode also covers self-certified architects, zoning review, inspections, demo permits, roughs and finals, dealing with delays, working with expediters, and how historical records like the SANS map can create unexpected issues years later.
Questions We Answer in This Episode
Q. Why should investors go through the permit process instead of avoiding it?
A. First, it is the right thing to do. Second, the downside of getting caught without permits is significant. If you are flagged, the city can require walls to be opened, work redone, and inspections repeated, often with no flexibility. Permits also protect resale value and catch design or code issues early.
Q. When should an architect be brought into the process?
A. As early as possible. Ideally during or even before attorney review. Getting an architect involved early allows investors to uncover zoning, setback, light, ventilation, and structural issues before closing, saving time and money later.
Q. What is a self-certified architect and why does it matter?
A. A self-certified architect has completed additional training with the city. Their plans bypass the Department of Buildings review and go straight to zoning, which can save weeks or months. The tradeoff is that mistakes may be caught later in the field instead of during plan review.
Q. What role does zoning play even with self-certification?
A. Zoning still reviews every project. Setbacks, floor area ratio, lot coverage, and unit counts are all reviewed by zoning, even for self-certified plans. This provides a layer of protection before construction begins.
Q. How important is investor input during preliminary drawings?
A. Extremely important. Preliminary drawings are where layout, functionality, and livability must be reviewed. Investors should evaluate room sizes, closet space, mudrooms, kitchens, TV placement, and traffic flow using real comps, not assumptions.
Q. What are common layout mistakes investors make?
A. Undersized primary bedrooms and closets, low basement ceiling heights, poorly placed stairwells, wasted front rooms, lack of mudrooms, and missing storage. These issues are difficult and expensive to fix later.
Q. How long does it take from hiring an architect to submitting plans?
A. Typically five to six weeks. This includes site visits, preliminary drawings, revisions, debt checks, contractor listings, and final construction drawings.
Q. What is a city debt check and why does it matter?
A. The city checks for unpaid parking tickets, water bills, and other municipal debt tied to the owner. Even bills due within days can delay permits, so these must be cleared before submission.
Q. Do contractors need to be listed before permits are approved?
A. Yes. Plumbing, electrical, HVAC, and other trades must be listed on the permit application, even before final pricing is complete. Changing contractors later is possible but costs time and money.
Q. Can construction start before permits are issued?
A. No. Demo that involves walls, plumbing, or structural elements requires permits. Starting early risks stop-work orders, fines, and extended delays.
Q. How does the demo permit process work?
A. Demo work must be done by licensed demolition contractors who handle their own permitting. Landscapers or general labor cannot legally perform demo work.
Q. What inspections should investors expect during construction?
A. Four primary rough inspections, new construction, HVAC, plumbing, and electrical, all before insulation and drywall. Finals for each trade occur after construction is complete.
Q. Where do timelines typically get delayed?
A. Rough inspections. A single failed inspection can add weeks. Scheduling inspectors, subcontractors, and re-inspections often results in six to eight weeks of inactivity if not planned correctly.
Q. Should investors attend inspections?
A. Investors should not be hands-off. While they may not attend every inspection, they should conduct pre-inspection walk-throughs with contractors to ensure readiness.
Q. What role do expediters play today?
A. Experienced city architects often handle much of what expediters do. Expediters are most useful when navigating unusual situations, zoning variances, administrative adjustments, or when relationships are needed to move stalled projects forward.
Q. What is the SANS map and why does it matter?
A. The SANS map is an old city record used to verify historic unit counts and building features. Structures not shown on the map may be deemed illegal, even if they existed for decades.
Q. Can undocumented structures be saved?
A. Sometimes. Proof such as old surveys, photos, window records, or lead tests can establish age and legality, allowing features to remain.
Q. How do historic or landmarked buildings affect permits?
A. These properties require additional approvals and dramatically longer timelines. Investors must check zoning and historic status early.
Show Notes
00:00 Why investors avoid permits
02:48 Working with self-certified architects
04:37 Site visits and preliminary layouts
06:44 Reviewing preliminary drawings correctly
09:40 Common layout and livability mistakes
14:19 Debt checks and contractor listings
17:17 Timeline from architect to submission
20:06 Zoning review and self-certification
21:17 Expediters explained
23:16 Demo permits and inspections
24:28 Rough inspections and delays
30:07 Field changes and plan revisions
31:24 SANS map issues
34:48 Self-inflicted permit problems
35:15 Historic and ADU considerations
35:29 Personal wrap-up and Chicago fact
Key Takeaways for Chicago Investors
Permits protect downside and resale value.
Architect selection directly impacts timelines.
Preliminary drawings are where most value is created or lost.
Rough inspections cause the largest delays.
Early planning saves months of holding costs.
Most permit problems are self-inflicted.
Guest Name: Tom Shallcross
Guest Company: Straight Up Chicago Investor
Guest Link: https://www.instagram.com/tshallcross723/
Because finding good tenants and property management shouldn’t feel like online dating.
Dear Investor,
If you are an investor in either the city or suburbs of Chicago, I would love to speak with you about how we can help you on your real estate journey. At GC Realty & Development LLC, we help hundreds of Chicagoland real estate owners and brokers each year manage their assets with both full service property management and tenant placement services.
We understand that every investor’s goals are unique, and we love learning about each client’s individual needs. If there is an opportunity to help you buy back your time by managing your rental property or finding quality tenants, please check us out.
Best Investing,
Founder, Partner, Podcast Co-Host, and Investor
