Why a Chicago Business Needs a Local CPA Who Actually Knows Illinois
Most Chicago business owners do not need another generalist who treats Illinois like a footnote. You need a CPA who keeps up with the Illinois Pass-Through Entity (PTE) tax election, who can explain Cook County personal property changes without putting you to sleep, and who actually returns the email.
That is the firm we built. Thompson Flaherty is an Illinois-licensed CPA firm headquartered in the Metro East and now serving Chicago and the suburbs. We work with small business owners, founders, professional service firms, and families who want a year-round CPA, not just a tax preparer who shows up in April.
If you would like to talk through where your business sits and what a year-round CPA relationship would look like, get in touch with our Chicago team.
Where We Serve in Chicago
We serve clients across the Chicago city limits and the surrounding suburbs. The names below are the areas where most of our Chicago clients sit, but if you do not see your neighborhood, the answer is almost certainly that we serve it too.
Chicago city neighborhoods we serve: Lincoln Park, Near North, Streeterville, River North, West Loop, Gold Coast, Lake View, Lincoln Square, Bucktown, Wicker Park.
North Shore and northern suburbs: Evanston, Skokie, Niles, Lincolnwood, Morton Grove, Glenview, Northbrook, Highland Park, Winnetka, Kenilworth, Northfield, Wilmette, Deerfield.
Western and southwestern suburbs: Oak Brook, Hinsdale, Naperville, Barrington, Des Plaines.
We are licensed in Illinois and Missouri, and most of the year-round client work is virtual. So whether you are in River North or Naperville, the working relationship is the same.
What a Chicago CPA Costs and What You Actually Get
Chicago CPA pricing varies widely, and most firms refuse to publish numbers. We do not love that. Here is roughly where the market sits for a small business in the Chicago area.
Tax return only (S-corp or LLC, no bookkeeping): around $1,200 to $3,500 depending on entity, multi-state filings, and complexity.
Monthly bookkeeping (a true monthly close, not just a year-end clean-up): roughly $400 to $1,500 a month based on transaction volume, payroll, and the number of accounts.
Year-round CPA relationship with bookkeeping, tax strategy, and quarterly check-ins: most of our Chicago clients land between $1,200 and $3,000 a month, all-in.
Pricing is one of those things that should be a conversation, not a guess. If you want a real number for your situation, our business tax services page walks through what we do at each engagement level, and we can quote from there.
How Illinois Taxes Are Different (And Why That Matters)
Illinois is a flat-income-tax state at 4.95%. That sounds simple until you start layering on the Personal Property Replacement Tax for S-corps and partnerships, the optional PTE tax workaround for the federal SALT cap, the Cook County minimum wage rules that drag payroll compliance with them, and the city of Chicago Lease Tax for software that catches a lot of out-of-state owners off guard.
A Chicago CPA who actually lives in this code can save you real money, mostly by avoiding overpayment on the PTE election when it does not benefit you, and by structuring owner comp on an S-corp so the math works for both the federal and the Illinois side. The Illinois Department of Revenue publishes the PTE rules in detail, and we work them into every Illinois entity return.
When Should a Chicago Business Switch to an S-Corp?
The short version: when your business profit is comfortably above what you would pay yourself as a reasonable W-2 salary, an S-corp election starts saving you self-employment tax. Most Chicago single-owner businesses cross that line somewhere between $80,000 and $100,000 of net profit, but it depends on the industry and what a reasonable salary actually looks like for the work you do.
There is a longer version. The S-corp election affects payroll setup, quarterly estimated payments, retirement plan contribution math, Illinois PTE eligibility, and whether the QBI deduction still works in your favor. We walk through it on our business tax services page, and it is a conversation worth having with your CPA before you file the election.
Bookkeeping vs. Accounting vs. CFO Work — What Chicago Owners Actually Need
Bookkeeping is the day-to-day record. Categorizing transactions, reconciling accounts, running payroll, keeping the books current. Most Chicago small business owners need monthly bookkeeping if revenue is past about $250,000 a year.
Accounting is the cleanup and interpretation. Monthly close, financial statements, the cash-to-accrual conversion, sales tax filings, and making sure the numbers you act on are right.
CFO work is the strategy layer. Cash forecasting, budgeting, pricing decisions, hiring math, owner take-home planning. Usually starts to make sense around $1M in revenue or when the owner is making decisions that go past gut feel.
Our Chicago accounting and bookkeeping services run the full stack, and you can pick where your business needs us today.
What Makes a Good Chicago CPA Different
Most firms in Chicago will quote you a tax return and tell you when the deadline is. That is the floor, not the bar. What you should expect from a good CPA, in our view:
A real conversation in the off-season, not just at extension time. Quarterly check-ins where we look at where the year is tracking and whether the estimated payments still make sense.
Proactive notice when something changes in the code that hits your situation, instead of finding out about a tax law change six months after it took effect.
Direct answers in plain language. If we cannot explain the move on a phone call, it is probably not the right move.
A CPA who knows your business, your industry, and your goals. Not just your tax return.
Industries We Work With in Chicago
We are a generalist firm by design. Most of our Chicago clients fall into one of these buckets: professional services (lawyers, consultants, agencies, architects, designers), e-commerce and product businesses, real estate investors and small landlords, healthcare practices and dental groups, restaurants and hospitality, and small SaaS or tech startups in the early-stage range.
Every one of those has its own tax wrinkles, and we map the engagement to the industry. If your business is in a highly specialized niche that needs a niche-only firm, we will tell you that on the first call.
How to Get Started With Thompson Flaherty in Chicago
The first step is a conversation. We start with a no-cost intro call, look at where your business sits today, and tell you honestly whether we are the right firm. If we are, we will quote the engagement on the call. If we are not, we will tell you who we would refer you to.
Reach out through our contact page and we will get a Chicago intro call on the calendar.
FAQ
Do you meet with Chicago clients in person?
Sometimes, yes. Most of the working relationship is virtual because that is what most clients prefer, but in-person meetings in the Chicago area are available when the situation calls for it (a complex acquisition, a partnership wind-down, or just preference).
Are you licensed to file Illinois taxes?
Yes. We are an Illinois-licensed CPA firm. We are also licensed in Missouri and serve clients across the broader St. Louis metro area, but Illinois is the home base and the largest share of our practice.
Do you handle multi-state filings for Chicago businesses that sell across state lines?
Yes. We file in every state where a client has nexus, and we run a quarterly nexus check for clients who sell into multiple states or have remote employees. Multi-state work is one of the more common things we do for Chicago e-commerce and SaaS clients.
What software do you support?
QuickBooks Online is the default. For payroll management, we use ADP. To manage receipts and document workflow, we use a secure client portal and integrate with the bank feed directly.
Will you help if my books are a mess?
Yes, that is one of the things we are actually good at. Catch-up bookkeeping for prior years is quoted separately from the ongoing monthly engagement, and we will give you a clear cost up front before any work starts.
How is your firm different from the big Chicago CPA firms?
Big firms are built for large companies. We are built for small businesses, founders, and families who want a partner relationship, not a transaction. You will work with the same CPAs every year. The phone calls get returned. The advice is for your business, not a template.
Ready to Talk to a Chicago CPA?
If your Chicago business is past the DIY phase or your current firm has stopped feeling like a partner, get in touch. We will tell you honestly whether Thompson Flaherty is the right fit. Schedule a Chicago intro call here.