How to sell a business in Chicago: the nine-month timeline, step by step.

Most owners sell one business in their life. The buyer across the table has usually bought several, and their accountant has read hundreds of sets of books. This article is the calendar we walk owners through in the first meeting: what happens in each month, who does the work, what it costs, and where the months get added. It is written for a family- or founder-owned company doing $1 million to $15 million in revenue in Chicago or the collar counties, and most of it holds anywhere in Illinois. The Chicago-specific version, with our three paths and the closing notices, is on sell my business in Chicago.

Where do I start if I want to sell my business?

Start with a number, not a listing. Before you talk to a broker, a buyer, or your brother-in-law, find out what the business would sell for today and what a buyer's accountant would push on. Our version is the free confidential value range: revenue, industry and an email address, and a CPA-prepared range comes back within two business days. Any competent advisor can give you something similar. What matters is that the range is built on your real earnings, not on a multiple pulled from a headline.

The second thing to settle is whether to sell now or fix first. Fewer than one in three owners have a written exit plan when the first buyer calls (Exit Planning Institute), and the ones who do tend to get better terms, because they had time to fix the two or three items that move a price most. Sometimes the right answer is to wait a year. You should hear that in the first conversation, not after a listing agreement is signed.

What should I fix before going to market?

A buyer's accountant tests the same five things every time: whether the financials hold up, how much of the business lives in the owner's head, whether the customers will stay, whether the team and the processes run without you, and whether the deal file is ready. We call them the five buyer lenses, and the pre-sale months are spent on the ones that would cost the most at the table.

The usual list, in the order it comes up:

• Books on an accrual basis with a monthly close. Cash-basis books get rebuilt by the buyer's accountant, and a business the buyer had to rebuild is priced with a discount for what they could not verify.
• Add-backs documented, not asserted. Every owner expense you want added back to earnings needs the invoice, the reason, and the year. An undocumented add-back is worth zero to a buyer.
• Customer concentration. One customer over about 20 percent of revenue lowers offers and changes structure, usually toward an earn-out. If that customer is on a handshake, get a contract or at least a history.
• Owner dependence. The sales relationships, the pricing decisions, the key supplier: if they all run through you, the buyer is paying for something that leaves at closing. A year of moving them to a second person is worth more than any marketing.
• The deal file. Leases, contracts, permits, the equipment list, the org chart, three years of tax returns, reconciled to the financials. Assembled before anyone asks, so diligence takes weeks instead of months.

Two weeks is enough to score all five and price the gaps; that is what the Exit-Readiness Review does. Ninety days is enough to fix the cheap ones. Some items, like reducing a 40 percent customer to 20, take a year or two, and the honest advice is to start them now and sell later. The seven things a buyer's accountant finds first covers what each one costs at the table.

How do I price a business for sale?

Small and mid-sized businesses sell on a multiple of earnings. For an owner-operated company under about $2 million in transaction value, the earnings measure is seller's discretionary earnings, and Chicagoland deals in our 2026 reference range from roughly 1.6 to 3.6 times SDE depending on industry and size, with manufacturing and distribution commonly at 2.7 to 3.1. Larger companies with $1 million to $10 million of EBITDA trade at about 3.7 to 4.5 times EBITDA, and the multiple steps up with size. The full table, with the publisher and year for each range, is on what Chicagoland businesses actually sell for, and the math behind a range is on how much is my business worth.

The listing price is set from a pricing memo: normalized earnings, documented add-backs, a working-capital target, and comparable transactions. A price a buyer's accountant can take apart in an afternoon is not a price, it is an opening position that gets retraded in diligence. Overpricing costs time as well; a business that sits on the market for a year gets a reputation among the buyers who matter.

How do I find buyers without telling my employees?

A marketed sale runs on a blind profile: one page that describes the business, its earnings and its location in general terms, without naming it. It goes to a buyer list you approve. Buyers who respond sign a non-disclosure agreement before they see a financial statement, and they are vetted, for funds and for fit, before they learn the company's name. The serious ones then get the confidential information memorandum and the financial package, and the two or three best of those meet you, usually at the business after hours.

Four kinds of buyers show up for a Chicagoland company in this size range. Roll-ups and private-equity-backed platforms, who pay for proven earnings and a team that stays. Strategic and competitor buyers, who want the customers and the crew and can pay for synergies. Individual buyers and searchers, who depend on a lender and are therefore the most sensitive to clean books. And insiders: a manager, a partner, a child, who need a real process to protect the relationship and the price. Which rooms to walk into depends on the business; a machine shop with a union and a long lease draws a different list than a dental practice.

Ninety to 120 days on the market is typical for a prepared business. That covers the profile going out, NDAs, the memorandum being read, management meetings, and offers coming in. Most teams never learn a sale is being prepared; you decide when your people are told, and it is usually after the purchase agreement is signed.

What happens between the letter of intent and closing?

The letter of intent is where the deal is really made. It sets the price, the structure (how much is cash at closing, how much is a seller note or an earnout), the working-capital target, the transition period, and an exclusivity window for the buyer. Everything after it is the buyer checking that what they were told is true, so an LOI negotiated carefully saves months. Two numbers to settle in the LOI rather than later: the working-capital peg, which is trued up at closing and can move the cash you receive by six figures, and what happens to the price if diligence turns something up.

Diligence runs from a data room. If the deal file was assembled before the sale, it is 60 to 90 days of answering questions once and well. If it was not, it is the same 60 to 90 days plus however long it takes to find the documents, with the buyer's confidence dropping each week. The buyer's lender adds a clock of its own: an individual buyer financed through a bank needs underwriting, an appraisal, and often a landlord's consent to assign the lease. Meanwhile your attorney and theirs negotiate the purchase agreement, the representations and warranties, and the non-compete.

What does closing look like in Illinois?

Two Illinois notices belong on the calendar the day the LOI is signed. In an asset sale, the buyer files Form CBS-1, the Notice of Sale, Purchase, or Transfer of Business Assets, with the Illinois Department of Revenue at least ten business days before closing, and the Department issues a release once the seller's state taxes are settled; a buyer who skips it can be held liable for the seller's unpaid Illinois taxes up to the value of the assets, so every buyer's attorney insists on it (source: Illinois Department of Revenue, Form CBS-1 instructions). A business that pays or remits Cook County taxes also files the county's Notice of Bulk Sales or Transfer at least 45 days before the sale (source: Cook County Department of Revenue). Forty-five days is longer than most owners expect, which is why it is raised at the LOI and not the week of closing.

The rest is mechanics that still need a steady hand: the purchase-price allocation for tax, which the buyer and seller want to go different ways; the lease assignment; the funds flow; the transition plan for the first 90 days after the wire. Your attorney runs the legal side and your CPA the tax side. On our deals Jim Calloway coordinates the closing (he has been through more than sixty of them) and Alex Nejad, CPA, handles tax and working capital. Selling outside Cook County or across the Indiana line? The Illinois guide covers the six counties and Northwest Indiana.

How long does it take to sell a business in Chicago?

Selling a business in Chicago takes six to nine months from the first conversation to the wire for a company with clean books: two weeks to 90 days of preparation, 90 to 120 days on the market, and 60 to 90 days from the letter of intent to closing, which has to fit Cook County's 45-day bulk-sales notice. A direct sale to a known buyer closes in 90 to 120 days. Here is where the months go, month by month.

A direct sale, to a buyer you already know or to a firm that acquires businesses outright, skips the marketing months and can close in 90 to 120 days. That is the case when we buy a business ourselves: a written indication of price, structure and timing before any listing work, no commission, and the owner stays free to go to market instead. For a manufacturer, how fast a manufacturing sale can close in Illinois runs the same clock with the equipment file and the Illinois filings on it.

Do I need a broker to sell my business?

Not always. If a competitor, a roll-up, or a key employee has already made a credible approach, you may need representation in that one negotiation rather than a marketed listing, and you should think twice before signing an exclusive agreement that pays a commission on a buyer you found yourself. What you still need is defensible financials, a price with evidence behind it, and someone to manage diligence, because the buyer's accountant does the same work either way. The decision, case by case, is in should I hire a business broker to sell my company.

If the buyer has to be found, a marketed sale is how most businesses in this size range change hands. In Chicago the success fee runs 8 to 12 percent of the sale price, paid at closing, and 10 percent is the number you will hear most (the same range holds for what a business broker charges in Illinois); above about $2 million, sliding scales such as Double Lehman bring the effective rate to 4 to 8 percent. Minimums, upfront fees and the tail clause are the terms that change what you actually pay, and they are covered clause by clause in business broker fees in Chicago, with a side-by-side table on the fee guide. Our terms are on how we sell a business: 10 percent, in writing before market, no retainer.

Why now, and not in five years?

About four in ten U.S. small businesses are owned by baby boomers, and McKinsey's 2026 estimate is that roughly six million U.S. businesses will change hands by 2035. In Chicagoland that means a lot of machine shops, distributors, trades contractors and practices coming to market in the same decade, and buyers with the same amount of money to spend. A prepared business in a crowded market still sells well. An unprepared one competes on price with every other unprepared one. The owners who do best are the ones who started the fixes two years before they needed to sell, which is a long way of saying the best time to get the value range is before you think you need it.

Common questions