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Serving Chicago · Nationwide

Bookkeeping Services in Chicago, IL

Chicago is the freight capital of North America, and its service economy shows it: thousands of trucking companies, dispatch operations, and repair shops orbit the rail yards and intermodal terminals, while the neighborhoods keep armies of HVAC, plumbing, and roofing crews busy fighting the lake-effect winters. Hard-season trades and freight economics are exactly the books we specialize in.

Our deepest Chicago work: trucking and freight Trucking , HVAC contractors who live on the seasonal swing HVAC , roofers Roofing , and the moving companies that churn through Chicago's rental cycle Moving .

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  • QuickBooks Gold ProAdvisor
  • Intuit Certified Bookkeeper
  • Intuit Enterprise Suite Certified
  • IRS PTIN Holder

What we handle for Chicago businesses

State and local issues we review during scoping

These are the state and local items we review during scoping and help you coordinate, including with your payroll provider. Complex multi-state or local-tax matters may require an appropriate specialist, and nothing here is automatically included until it is scoped in your engagement.

  • Illinois payroll withholding and IDES filings alongside payroll
  • Chicago's local tax layer (lease transaction, restaurant, and license obligations) tracked where it touches you
  • Sales tax across home-rule jurisdictions reviewed and coordinated when in scope
  • Trucking-friendly books in America's freight capital. IFTA, settlements, per-truck P&L

Virtual-first, and it works

Everything runs online: QuickBooks Online for the books, secure sharing for documents, video calls on a schedule. That is how a Chicago business gets a bookkeeping team that actually knows its industry, with a monthly close date in writing and no office visits required.

Ivan Dyakov, founder of Steady Tax & Bookkeeping

Founder-led service

Ivan Dyakov

Ivan leads client strategy, major relationships, and service standards, supported by a specialized delivery process built for consistency.

Meet the founder
  • QuickBooks Gold ProAdvisor
  • Intuit Certified Bookkeeper
  • Intuit Enterprise Suite Certified
  • IRS PTIN Holder

A clear next step

Ready for a steadier back office?

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