Hiring the wrong contractor costs more than the job itself. Here's the complete checklist for evaluating contractors in Chicago — from licensing to red flags.
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.
In Illinois, different trades have different licensing requirements. Here's what to verify:
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.
A verbal agreement is not a contract. Before any work begins, you should have a written document that includes:
Beyond the non-negotiables, here's how to evaluate contractors:
How a contractor communicates before the job is how they'll communicate during it. Look for:
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.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.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.Hiring the wrong contractor is one of the most expensive mistakes you can make. 🚨 Here's what to check BEFORE you sign anything: ✅ Verify their license (idfpr.illinois.gov for IL) ✅ Get a Certificate of Insurance ✅ Get everything in writing — scope, materials, timeline, payment ✅ Never pay more than 30% upfront ✅ Check Google & Yelp reviews for specifics, not just stars ✅ Walk away if they can't provide references 34 years in Chicago. We've seen every contractor mistake in the book — and we've built our business on doing the opposite. 📞 (312) 313-3878 🌐 myhandymanexpress.pro #ContractorTips #HiringContractor #ChicagoContractor #HomeRepair #PropertyMaintenance #RealEstate #MyHandymanExpress
34 years of Chicago experience. Licensed & insured. 5.0 stars on Google & Yelp.