Running a business or managing investment income in River North means dealing with complex tax situations that generic tax software simply cannot handle. Between Illinois’s Pass-Through Entity tax election, the recently enacted One Big Beautiful Bill Act reshaping federal deductions, and Chicago’s layered local tax requirements, the cost of getting it wrong keeps climbing. If you’re a business owner, self employed professional, or real estate investor in the River North neighborhood, Massey and Company CPA delivers the tax services, accounting, and proactive planning that keep you compliant and stop you from overpaying taxes.
Call (773) 828-0551 for a free consultation or visit masseyandcompanyCPA.com to get started.
Founded in 2013 by Gary Massey, a CPA who brings over 30 years of hands on experience in tax preparation, tax planning, and IRS and state tax resolution
Certified QuickBooks ProAdvisors – Staff-level expertise in cloud-based bookkeeping systems means your financial reporting is accurate, real-time, and built on infrastructure that scales with your business
4.9-star rating across 238 reviews on Trustindex, with clients consistently highlighting responsiveness, professionalism, and clear communication
Prompt responses and no surprise billing – Transparent pricing and a commitment to returning client communications within 24 hours. Not just during tax season, but year-round
River North is not an average small business market. With a median household income of roughly $153,373 and approximately 44% of households earning over $150,000, the tax and accounting needs here demand a firm that understands high-income professional services, real estate investment structures, and multi-state filing complexities. While CPA firms vary from boutique practices to larger advisory firms, Massey and Company CPA has built its Chicago office around River North needs in a way many Chicago accountants do not.
Deep knowledge of the Chicago market and Illinois tax law – Massey’s team handles the specific compliance and planning challenges that River North residents and businesses face, translating regulatory complexity into real dollar savings
Specialized experience across River North industries – Tech startups, creative agencies, hospitality businesses, real estate investors, and finance professionals all get tailored strategies rather than one-size-fits-all tax return preparation
Proactive planning that works year-round – Instead of scrambling at tax time, Massey and Company CPA builds ongoing relationships that identify deductions, restructure entities, and adjust to law changes like the One Big Beautiful Bill Act before filing deadlines arrive
Direct IRS representation that protects your interests – When an IRS notice shows up or an audit begins, Massey’s licensed CPAs and Enrolled Agents step in to communicate with federal and state authorities on your behalf
River North clients come to Massey and Company CPA with specific problems: a business tax return that keeps getting more complicated, bookkeeping that has fallen behind, an IRS letter demanding attention, or a tax strategy that hasn’t been revisited in years. Every service below is designed to solve those tax, bookkeeping, and accounting services problems directly.
Massey and Company CPA handles annual tax preparation for individuals, families, and every major business entity – LLC, S corp, C corp, partnerships, nonprofits, trusts, and estates. Common business filings may involve forms such as Form 1120S or Form 1065. For River North’s high-income professionals and business owners, that means more than just filing. The firm builds proactive tax planning strategies around entity selection, retirement contributions, charitable giving, and maximizing available deductions and credits; with careful review, CPAs often uncover missed deductions worth $15,000–$50,000, including items like vehicle mileage when records support the claim.
Multi-state tax filing is a core competency, not an afterthought. If you earn income outside Illinois – whether from rental properties, consulting engagements, or remote work arrangements – Massey ensures proper apportionment and allocation across every jurisdiction. With the SALT deduction cap now raised to $40,000 through 2029 under the One Big Beautiful Bill Act, and Illinois’s PTE election allowing partnerships and S corporations to pay state income tax at the entity level at 4.95%, the interplay between federal and state tax strategy has never been more consequential. Massey helps clients evaluate whether the PTE election reduces their overall tax liability – and for eligible owners, an S-Corp election can also cut self-employment tax by $5,000–$20,000 – while handling the filing deadlines so nothing slips through.
New federal deductions under the One Big Beautiful Bill Act also require careful planning: tip income deductions up to $25,000, overtime pay deductions up to $12,500, qualifying auto loan interest deductions up to $10,000, and a $6,000 deduction for eligible seniors – all active for tax years 2025 through 2028. For River North’s hospitality business owners, sole proprietors, and senior professionals, these provisions create real savings when documented and filed correctly.
Clean books are the foundation of every smart tax strategy. Massey and Company CPA provides monthly and quarterly bookkeeping services, account reconciliations, financial statement preparation, and cash flow forecasting for small businesses and startups across River North. Whether you need a full clean-up of years of backlogged records or ongoing reconciliations that give you a clear picture of where your money goes, the firm delivers.
As Certified QuickBooks ProAdvisors, Massey’s team handles setup, migration, staff training, and system optimization. Cloud-based accounting means you access real-time financial data from anywhere – critical for business owners managing operations across the Chicago area or beyond. Financial reporting, budget tracking, and KPI dashboards help you make decisions based on current numbers, not last quarter’s guesses.
Facing an audit, collection action, or years of unfiled returns is stressful. Massey and Company CPA provides expert IRS representation at every stage – from correspondence audits and field audits to appeals, installment agreement negotiations, Offers in Compromise, and penalty abatement requests. Licensed CPAs and Enrolled Agents communicate directly with the IRS and the Illinois Department of Revenue so you do not have to.
Back tax preparation, wage garnishment intervention, lien releases, and compliance restoration are all within scope. If you have unfiled returns or unresolved liabilities, Massey works to get you current and negotiate the best possible resolution.
Massey and Company CPA offers fractional CFO and controller services tailored to River North businesses that need expert financial leadership without the full-time cost. These services provide strategic financial management, budgeting, forecasting, and cash flow analysis to help clients make informed decisions and drive growth.
The firm’s fractional CFOs work closely with business owners to develop customized financial strategies that align with their goals. By leveraging real-time accounting data and industry insights, Massey’s CFOs identify opportunities for cost savings, optimize working capital, and improve profitability.
Controller services focus on maintaining accurate financial records, managing accounts payable and receivable, and ensuring timely financial reporting. Massey’s team implements internal controls and compliance measures to safeguard assets and support audit readiness.
Whether your business is scaling rapidly or requires interim financial leadership during transitions, Massey and Company CPA’s fractional CFO and controller solutions provide the expertise and flexibility needed to navigate complex financial challenges in River North’s dynamic market.
Your engagement starts with a comprehensive review of your current tax situation, business structure, and accounting needs. Massey and Company CPA identifies potential savings opportunities, compliance gaps, and areas where you may be leaving money on the table – whether that is an entity restructuring, an unclaimed PTE election, or deductions you have been missing on an annual basis.
Based on your specific circumstances – whether you are a real estate investor with multiple rental properties, a restaurant owner navigating tip compliance, or a tech startup planning its first business tax return – Massey develops a tailored approach. This includes implementing the right accounting systems, selecting the optimal entity structure, and building a tax strategy aligned with both federal and Illinois requirements.
Tax planning does not end at filing. Massey and Company CPA provides year-round ongoing support, regular check-ins, and proactive communication about regulatory changes that affect your situation. When new legislation like the One Big Beautiful Bill Act shifts the landscape, your firm is already adjusting your plan – not scrambling after the deadline.
Massey and Company CPA’s proven track record in the Chicago area shows up in measurable outcomes for clients:
Tax savings through entity restructuring and PTE elections – Business owners structured as partnerships or S corporations who properly elected PTE treatment have reduced their effective federal tax burden by converting state taxes into entity-level deductions, bypassing SALT cap limitations that previously cost them thousands
Successful IRS resolution outcomes – Clients facing audits, penalties, and back tax liabilities have had cases resolved through Offers in Compromise, penalty abatements, and negotiated installment agreements, restoring compliance and eliminating the threat of liens or garnishments
Business growth supported by accurate financial reporting – Startups and established businesses alike have gained the clear picture of cash flow and profitability needed to make confident hiring, expansion, and investment decisions
Compliance improvements that prevent future problems – From cleaning up years of backlogged bookkeeping to establishing real-time cloud accounting systems, Massey helps clients build infrastructure that keeps them audit-ready
Massey and Company CPA serves clients throughout the River North neighborhood and across the broader Chicago metropolitan area, including:
Gold Coast – High-net-worth individuals and professional services firms
Lincoln Park – Small businesses, startups, and family tax preparation clients
Old Town – Creative agencies, restaurants, and hospitality businesses
The Loop and Downtown Chicago – Corporate offices, finance professionals, and consulting firms
Streeterville, Lakeview, and North Side communities – Entrepreneurs, investors, and self employed professionals across the Chicago area
Whether your office is on Wacker Dr or you run your business from a home office in any of these neighborhoods, Massey and Company CPA works with you remotely or in person through its Chicago office.
Massey and Company CPA provides transparent pricing based on the complexity of your situation. Tax return preparation for an LLC or S corp typically ranges from $1,200 to $3,500 depending on entity structure, number of states, and transaction volume. Monthly bookkeeping services generally range from $500 to $1,500 based on the number of accounts, payroll complexity, and reporting requirements. IRS representation and tax resolution are scoped and quoted after the initial consultation. There are no surprise bills.
Massey and Company CPA is committed to prompt responses – not just during tax season, but year-round. For urgent matters like an IRS notice or active collection action, the firm prioritizes rapid engagement. Standard tax preparation and planning engagements are scheduled based on complexity and deadline, with clear timelines set during your initial consultation.
Yes. As Chicago accountants, Massey and Company CPA works with small businesses, startups, sole proprietors, and self employed professionals across every major industry in River North – from tech and creative services to hospitality, real estate, and finance. The firm provides business advisory, tax and accounting, bookkeeping, payroll support, and strategic planning designed to help businesses reach their full potential in the Chicago market.
Absolutely. Massey and Company CPA specializes in back tax preparation and unfiled return filing. The team prepares delinquent returns, negotiates penalty abatement with the IRS and Illinois Department of Revenue, sets up installment agreements, and pursues Offers in Compromise where appropriate. The goal is to restore full compliance and resolve outstanding liabilities as efficiently as possible.
The Illinois Pass-Through Entity tax election allows qualifying partnerships and S corporations to pay state income tax at the entity level at a rate of 4.95%. For business owners affected by the federal SALT deduction cap, this election can significantly reduce overall tax liability by converting what would be a personal state tax payment into a deductible business expense on the federal return. The election is irrevocable after the extended due date, which makes getting expert guidance from a tax accountant before filing critical. Massey and Company CPA evaluates whether PTE election makes sense for your specific situation and handles all required filings.
Stop leaving deductions on the table and start working with a CPA firm that understands the River North business landscape, Illinois tax law, and the federal changes reshaping your tax strategy right now. Massey and Company CPA is ready to put its team of licensed CPAs and Enrolled Agents, led by its managing partner, to work for you.
Massey and Company CPA · (773) 828-0551 · masseyandcompanyCPA.com · Or reach out to us by email at info@masseyandcompanyCPA.com. Serving River North, Chicago and surrounding neighborhoods
