Professionals in Chicago

Freelance bookkeepers: $25–$50/hour. Professional bookkeeping firms: $40–$80/hour. Monthly packages for small businesses: $300–$800/month depending on transaction volume. Payroll add-on: $50–$150/month. Year-end prep: $500–$1,500 one-time. Always ask what's included.

Bookkeepers handle daily financial records: data entry, reconciliation, invoicing, payroll. Accountants provide higher-level services: tax strategy, financial statements, CRA audits, business advice. Most small businesses need a bookkeeper year-round and an accountant for tax season.

Hire a bookkeeper when: you're spending 5+ hours/month on books, you've missed a tax deadline, your records are behind, you're hiring employees (payroll), or your business revenue exceeds $50K. The cost of a bookkeeper is almost always less than the cost of mistakes.

No certification is legally required, but look for CPB (Certified Professional Bookkeeper) from the Canadian Institute of Bookkeeping, or QuickBooks ProAdvisor / Xero Certified. These demonstrate training and competency. Always ask about their experience with businesses like yours.

Bookkeepers can prepare and file simple tax returns (T1, T2, HST/GST). For complex tax situations — corporate restructuring, tax planning, CRA audits, international tax — you need a CPA. Many bookkeepers partner with accountants and can coordinate your year-end seamlessly.