The Contractor Problem in Chicago
Chicago has thousands of contractors. Some are exceptional. Many are mediocre. A few are outright fraudulent. The challenge for property owners is that it's genuinely difficult to tell the difference before the work starts.
The consequences of hiring the wrong contractor range from frustrating (poor quality work that needs to be redone) to catastrophic (non-code-compliant work that creates liability, safety hazards, or insurance complications).
After 34 years in the Chicago construction and maintenance industry, we've seen every type of contractor failure. Here's the complete checklist we'd give to any property owner evaluating contractors.
The Non-Negotiables
1. Verify Licensing
In Illinois, different trades have different licensing requirements. Here's what to verify:
2. Verify Insurance
Every contractor you hire should carry two types of insurance:
General Liability Insurance: Covers property damage and bodily injury caused by the contractor's work. Minimum $1 million per occurrence for any significant project. Workers' Compensation Insurance: Covers injuries to the contractor's employees while on your property. Without this, you can be held liable for injuries that occur on your property.Ask for a Certificate of Insurance naming you as an additional insured. A legitimate contractor will provide this without hesitation. If they balk, walk.
3. Get Everything in Writing
A verbal agreement is not a contract. Before any work begins, you should have a written document that includes:
- Detailed scope of work (what's included and what's not)
- Materials to be used (brand, model, grade)
- Start date and estimated completion date
- Payment schedule (never pay 100% upfront)
- Warranty terms
- Change order process
The Evaluation Checklist
Beyond the non-negotiables, here's how to evaluate contractors:
Reviews and References
- Look at Google and Yelp reviews — not just the star rating, but the content
- Look for reviews that mention specific projects similar to yours
- Ask for 2–3 references from recent, similar projects
- Actually call the references
Communication Quality
How a contractor communicates before the job is how they'll communicate during it. Look for:
- Prompt responses to calls and emails
- Clear, specific answers to your questions
- A written estimate (not just a verbal number)
- Willingness to explain their process
The Estimate Process
A quality contractor will want to see the job before quoting it. They'll ask questions about your timeline, your priorities, and any constraints. They'll provide a written estimate with line items.
Red flag: A contractor who quotes a job without seeing it, or who provides a single lump-sum number without any breakdown.Subcontractor Disclosure
Many general contractors use subcontractors for specialized trades (electrical, plumbing, HVAC). This is normal and acceptable — but you should know who's working on your property.
Ask: "Will you be using any subcontractors? If so, are they licensed and insured?"
Red flag: A contractor who won't disclose their subcontractors or who can't confirm their subcontractors are licensed and insured.Red Flags to Walk Away From
- Demands full payment upfront. No legitimate contractor requires 100% payment before work begins.
- No physical address or business presence. A contractor with only a cell phone number and no verifiable business address is a risk.
- Significantly lower bid than all others. If one bid is 40% lower than the others, either they're missing something in the scope or they plan to cut corners.
- Pressure to decide immediately. High-pressure sales tactics are a sign of a contractor who knows they won't win a fair evaluation.
- Can't provide a written contract. This is a dealbreaker.
- Asks you to pull the permit. Contractors should pull their own permits. If they ask you to pull it, they may not be licensed to do so.
Why We're Different
At My Handyman Express, we've built our reputation over 34 years on transparency, quality, and accountability. We're fully licensed and insured, we provide written scopes of work for every project, and we stand behind our work.
We're not the right fit for every project — but if you're looking for a contractor you can trust with your property, we'd love to earn that trust.
Schedule a free consultation or call (312) 313-3878.