Business Exit Planning
in Skokie, IL.
You built something worth selling. Now make the proceeds last.
For most business owners, the sale is the retirement plan. The proceeds have to replace the salary, the benefits, and the income stream you've depended on for decades. That's a high-stakes transition, and it requires more than just a financial advisor who handles 401(k)s.
At our firm, we've guided business owners in Chicago's Northern Suburbs through exits and liquidity events for nearly 50 years. We know the questions to ask before you sign, and the mistakes to avoid after the wire hits.
What this looks like in Skokie.
Skokie's commercial corridors along Dempster Street, Touhy Avenue, and Oakton Street are home to a diverse mix of small businesses, retail, restaurants, professional services, and light manufacturing, whose owners are approaching retirement. Business exit planning in Skokie often involves more modest transaction sizes than lakefront communities, with installment sale structures and seller financing more commonly discussed as tools to spread the tax impact across multiple years.
The county details.
Cook County business sellers face a tax environment with two important state-level considerations. Illinois taxes capital gains at the flat 4.95% rate with no preferential capital gains treatment, adding to the federal capital gains tax on the full gain. On a $3 million gain, the Illinois tax alone is approximately $148,500. The Illinois estate tax is equally important: business sale proceeds that substantially increase net worth can push a Cook County family well above the $4 million Illinois exemption, making pre- and post-sale estate planning essential. We address both the Illinois capital gains exposure and the post-sale estate tax picture before any deal closes.
Why Skokie.
Skokie offers retirees the best of both worlds, proximity to Chicago amenities with a more affordable cost of living than Evanston or Wilmette. Many of our Skokie clients are long-time residents who want to retire comfortably in the community they know.
Things Skokie families ask.
Down the shore.
Talk to a Skokie
advisor.
One free conversation about business exit planning, at your kitchen table, our Evanston office, or a video call.