Running a business or managing personal finances in Greektown means navigating one of the most complex tax environments in the country. Between federal obligations, Illinois’s flat 4.95% state income tax rate, Cook County assessments, and additional city taxes that Chicago residents pay on top of state taxes, the layers of compliance can drain your time and your bank account. Property taxes in Chicago are among the highest in the nation – a reality that hits Greektown’s commercial property owners especially hard as land values in the 60607 corridor continue to climb. Whether you’re a restaurant owner on Halsted Street, a real estate investor with mixed-use properties, or a professional earning well above the median household income of $119,500 in Greektown, proactive tax planning isn’t optional – it’s essential.
Massey and Company CPA delivers tax planning services, accounting solutions, and IRS representation built for the exact challenges Greektown businesses and residents face. With a deep understanding of Illinois and Chicago tax codes, the firm helps clients protect their income, stay compliant, and keep more of what they earn.
Call (773) 828-0551 for a free consultation or visit masseyandcompanyCPA.com to get started.
Choosing a CPA firm or accountant is a decision grounded in credentials, track record, and reliability. Massey and Company CPA has built trust through verifiable results and consistent service quality.
Founded in 2013 by Gary Massey, who brings over 30 years of hands on experience in tax preparation, tax planning, and IRS and state tax resolution
Professional credentials across the team: Certified Public Accountants, Enrolled Agents licensed by the IRS, QuickBooks ProAdvisors, and a founder who is a CPA and holds both a Master’s degree in Accounting and an MBA with a specialization in taxation
4.9-star rating across 238 reviews on Trustindex, with clients consistently highlighting responsiveness, professionalism, and clear communication
Rapid response times – clients report same-day or next-day callbacks even during peak tax season and on weekends
Adherence to AICPA and IRS ethical standards, with team members regularly updating their knowledge of evolving state and local tax regulations
Greektown’s approximately 28,797 residents in the 60607 ZIP code area need more than basic tax filing from someone they only hear from once a year. The services offered by Massey and Company CPA extend beyond annual tax preparation to ongoing consulting, strategic planning, and problem resolution – the kind of year-round partnership that keeps clients financially sound.
Outcome-driven tax strategy: Massey and Company CPA doesn’t just prepare returns – the team builds proactive tax strategies that can save high-income professionals $10,000–$50,000 yearly and save business owners $25,000–$150,000 annually through entity structuring, cost segregation, R&D credits, and asset depreciation planning
Local tax laws expertise: The firm has deep knowledge of Illinois and Chicago tax codes, including Cook County property tax procedures, sales tax collection obligations, and city licensing nuances – ensuring compliance and helping clients avoid costly surprises
IRS and audit protection: With professional representation that can reduce proposed audit assessments by 60–80%, Massey and Company CPA stands on behalf of clients when the stakes are highest
Modern technology that streamlines processes: Cloud-based bookkeeping through QuickBooks Online, secure document portals, and electronic filing allow for real-time access and updated records – giving clients the advantage of faster decisions and cleaner records without adding friction
Proactive approach over reactive filing: Dedicated tax planning is offered year-round rather than just during tax season, with scheduled strategic meetings, quarterly estimated tax management, and advisories as tax laws change
Massey and Company CPA offers a full range of tax services and accounting support designed around what Greektown clients actually need — from helping individuals minimize their tax burden to supporting small business owners with financial management and compliance across various industries, and to assist clients in reaching practical financial and business goals.
Effective tax planning minimizes liabilities and maximizes savings. For individuals, Massey and Company CPA handles Form 1040 filings, optimizes deductions, manages education savings plans, Roth conversions, and rental property tax shelters. For businesses, the team provides guidance on entity selection – such as LLC or S-Corp – along with business tax preparation, cost segregation for real estate investors, R&D credits, and retirement benefit strategies.
Industry-specific expertise is crucial for effective tax strategies in sectors like restaurants, which make up a significant portion of Greektown’s commercial base. Restaurants and startups particularly benefit from specialized CPA services in the Chicago area, where sales tax collection rules and payroll compliance add layers of complexity. The firm’s year-round tax planning helps avoid unwelcome surprises during tax season by managing quarterly estimated taxes and monitoring regulatory changes that affect your bottom line.
Accurate bookkeeping services form the foundation of smart financial decisions. Massey and Company CPA provides QuickBooks setup, clean-ups, and continuous cloud bookkeeping that saves time and ensures compliance. Their bookkeeping and reporting practices support accurate records and better financial decisions. Cloud-based bookkeeping allows for real-time access so clients always know where their finances stand.
Financial statement preparation and analysis – including P&L statements, balance sheets, and cash flow forecasts – give business owners the clarity to plan for growth. Payroll processing covers recording, tax withholding, and compliance with Chicago and Illinois payroll regulations, keeping your employees paid correctly and your organization protected from penalties. Accounting firms like Massey and Company help ensure timely reconciliations and accurate financial records that hold up under scrutiny.
When IRS notices, audits, or state agency letters arrive, having professional representation matters. Massey and Company CPA resolves IRS tax issues for clients through audit defense, responding to CP2000 letters, and handling communications with taxing authorities on your behalf. Professional accountants can reduce audit assessments by 60–80%, turning potentially devastating outcomes into manageable results.
The firm’s tax resolution services include negotiating Offers in Compromise with IRS assistance, setting up IRS payment plans, pursuing penalty abatement, and resolving liens and levies. For clients dealing with back taxes, the team can establish Currently Non-Collectible status where applicable. There is a rising emphasis on audit readiness among CPA firms, and Massey and Company conduct ongoing review to help clients mitigate risks before problems escalate.
Massey and Company CPA makes the engagement process straightforward – from first contact through ongoing support, every step is designed to reduce friction and deliver clear results.
Your first meeting is a free consultation where Massey and Company’s team reviews your documents, previous returns, and any notices you’ve received. They assess your financial situation, identify risk points, and evaluate exposure across federal, state, and local tax obligations. You’ll leave with specific recommendations and a clear engagement proposal – no vague promises, just a concrete plan tailored to your unique needs.
Once engaged, Massey and Company sets up technology platforms including secure portals and cloud accounting tools, then establishes service milestones – bookkeeping cycles, estimated tax preparation dates, and regular check-ins. Outsourcing CPA services allows business owners to focus on core operations while Massey and Company manages the accounting. Communication channels stay open through phone, email, and the client portal. Local CPA services provide increased compliance accuracy and fast response times for client queries, and reviews confirm that Massey and Company delivers on that standard even during the busiest weeks of tax season.
Clients receive completed tax filings, financial statements, and resolution of any outstanding notices – all prepared to be audit-ready. Follow-up meetings, often annual, focus on planning ahead: adjusting strategies for new tax laws, identifying additional savings opportunities, and keeping your financial position strong. Firms often provide financial forecasting and strategic growth planning for small businesses, and Massey and Company integrates this into their ongoing relationship with each client. Outsourced CFO services help manage cash flow and support strategic decision-making for businesses that need higher-level financial guidance.
Massey and Company CPA offers Fractional CFO and Controller services tailored to meet the needs of growing businesses in Greektown and the greater Chicago area. These services provide clients with high-level financial leadership and strategic insight without the full-time cost, making expert guidance accessible for small to mid-sized companies.
As a Fractional CFO, Massey and Company CPA helps businesses develop and implement financial strategies that drive growth, improve cash flow management, and enhance profitability. The firm assists with budgeting, forecasting, financial analysis, and key performance indicator (KPI) development, empowering business owners to make informed decisions based on accurate and timely financial data.
Controller services focus on managing day-to-day accounting operations, ensuring that financial records are accurate, up-to-date, and compliant with relevant regulations. Massey and Company CPA oversees bookkeeping, reconciliations, payroll, and internal controls, providing a solid financial foundation that supports operational efficiency and audit readiness.
By combining these services, Massey and Company CPA delivers comprehensive financial management that adapts to the evolving needs of businesses in competitive markets like Greektown. Clients benefit from personalized attention, expert advice, and scalable solutions that align with their growth objectives and tax planning strategies.
Client satisfaction at Massey and Company CPA is reflected in the specifics of what clients report. Local CPA firms typically emphasize personalized attention and partner involvement, and the reviews bear that out:
A chiropractor with a 30-year practice who switched to Massey and Company after working with other firms for decades noted that the team “exceeded expectations” in response time and professionalism
Multiple clients report that Massey and Company “resolved IRS issue with positive result,” “made process low stress,” and “finished returns early” – outcomes that reflect the firm’s commitment to client success
Real estate investors and business contractors highlight savings achieved through strategic planning, tax law insights, and efficient completion of filings
Clients typically save an average of $23,000+ per year with CPAs who take a proactive, planning-first approach – and Massey and Company’s track record demonstrates that kind of impact across the businesses and individuals they serve.
Massey and Company CPA serves clients throughout Chicago with a focus on the neighborhoods surrounding the downtown core:
Greektown (ZIP 60607) – including businesses within SSA #16
West Loop
Little Italy
University Village
South Loop
Near West Side
The Loop and surrounding downtown areas
The firm provides with multi-state tax compliance for clients whose business or investment activities extend beyond Illinois, and serves clients in the real estate sector, hospitality, professional services, nonprofits, consulting, and other industries across the Chicago metropolitan area.
Massey and Company CPA emphasizes fair, transparent pricing. Bookkeeping and accounting services typically use fixed monthly fees, while tax preparation fees depend on the complexity of your situation. The firm focuses on value – when hiring a CPA can save clients $25,000–$150,000 annually, the return on investment is clear. Local CPA firms improve accuracy in financial filings, which reduces risks of penalties that can far exceed the cost of professional services.
Clients consistently report same-day or next-day responses, even during peak tax season and on weekends. When urgent IRS or state agency letters arrive, the team prioritizes getting answers and taking action quickly. While no published guarantee exists for a specific hour window, the firm’s 4.9-star review track record across 238 reviews reflects a standard of responsiveness that clients rely on.
Yes. Massey and Company CPA works with small business owners, entrepreneurs, real estate investors, nonprofits, and individuals across various industries. Specialized CPA services are available for hospitality, real estate, professional services, and consulting – all sectors well-represented in Greektown. CPA services provide tax planning, bookkeeping, and business advisory services adapted to each client’s scale and industry. The firm also assists clients with entity selection during business formation, helping new businesses gain the right structure from day one.
Absolutely. The team includes Enrolled Agents and a founder who is a Certified Tax Representation Consultant. Services include audit defense, Offers in Compromise, penalty abatement, installment agreement negotiations, and resolution of liens and levies. Many CPA firms offer IRS representation for audits and disputes, but Massey and Company’s specific expertise in tax resolution – combined with Gary Massey’s 30+ years of experience – gives clients a strong advocate when facing the IRS or Illinois Department of Revenue. Tax professionals at the firm can help set up IRS payment plans and negotiate on your behalf to protect your assets and income.
Every day you wait on tax planning, compliance, or unresolved IRS issues costs you money. Massey and Company CPA is committed to helping individuals and businesses in Greektown achieve lower tax liabilities, cleaner financial records, and peace of mind – backed by integrity, expertise, and a proactive approach that keeps you ahead of problems.
Massey and Company CPA · (773) 828-0551 · masseyandcompanyCPA.com · Or reach out to us by email at info@masseyandcompanyCPA.com. Serving Greektown, Chicago and surrounding neighborhoods
