About Sterling & Associates
Chicago's trusted corporate law firm since 2005. We combine big-firm expertise with the personalized service and responsiveness that growing businesses deserve.
Built by Chicago, for Chicago
Sterling & Associates was founded in 2005 by James Sterling, a corporate attorney who spent a decade at one of the nation's largest law firms and saw firsthand the gap in the market: mid-sized Chicago businesses were underserved. They needed sophisticated corporate legal counsel but couldn't justify the rates and overhead of a mega-firm — and they deserved better than the generalists who couldn't keep up with complex transactions.
From day one, Sterling & Associates has been built around a simple promise: big-firm expertise with boutique-firm responsiveness and value. We hire attorneys from the best law schools and biggest firms, but we structure our practice to eliminate the inefficiency and overhead that drives up costs at larger firms.
Today, our team of five attorneys serves over 500 Chicago-area businesses across every major corporate legal discipline — from business formation and commercial contracts to M&A, securities compliance, IP protection, and complex litigation. We're proud to be the go-to corporate law firm for Chicago's growing businesses.
Years Combined Experience
Businesses Served
in Transactions Closed
Client Retention Rate
What Drives Everything We Do
Our values aren't just words on a wall — they're the principles that guide every client interaction, every legal strategy, and every business decision we make.
Integrity First
We provide honest, straightforward counsel — even when the advice isn't what you want to hear. Our clients trust us because we always put their interests ahead of our fees.
Results-Driven
Every engagement is measured by outcomes. We don't bill hours for the sake of billing — we focus on achieving the specific business objectives our clients need.
Client Partnership
We invest time to understand your business, industry, and goals. Our attorneys serve as true partners, not just outside counsel you call when something goes wrong.
Chicago Commitment
This is our city. We're deeply rooted in Chicago's business community and committed to helping local businesses thrive, grow, and compete at any scale.
Deeply Rooted in Chicago's Business Community
Chicago isn't just where we work — it's who we are. Every attorney at Sterling & Associates chose to build their career here because they believe in this city and its businesses. We understand the local regulatory landscape, the Cook County courts, and the unique dynamics of doing business in Illinois.
We're active members of the Chicago business community, serving on boards and advisory committees for organizations including the Executives' Club of Chicago, 1871, and the Chicago Bar Association. Our attorneys regularly speak at local business events and provide pro bono counsel to community organizations.
Our Wacker Drive office sits in the heart of Chicago's business district, and our clients span every neighborhood and suburb — from Loop-based startups to manufacturing companies on the South Side to technology firms in the West Loop corridor.
Two Decades of Growth
Firm Founded
James Sterling founded Sterling & Associates with a mission to bring sophisticated corporate legal counsel to mid-market Chicago businesses.
Weathering the Storm
Guided dozens of Chicago businesses through the financial crisis, earning a reputation for steady counsel in turbulent times.
Growth & Expansion
Expanded to our current Wacker Drive offices and grew the team to include litigation, securities, and IP capabilities.
100th Transaction
Closed our 100th M&A transaction, representing over $1B in cumulative deal value for Chicago businesses.
Digital Transformation
Invested in technology to provide seamless remote service during the pandemic, maintaining uninterrupted counsel for all clients.
25 Years Strong
Celebrating two decades of service with 500+ businesses served, $2B+ in transactions closed, and a 98% client retention rate.
Meet the Attorneys Behind the Results
Every attorney at Sterling & Associates brings top-tier credentials, years of real-world experience, and a genuine commitment to client success.
Our Office
Located on Wacker Drive in the heart of Chicago's business district, our offices offer a convenient and professional setting for client meetings. We're easily accessible by public transit and have nearby parking available.
Address
225 W Wacker Dr, Suite 2100, Chicago, IL 60606
Office Hours
Monday – Friday: 8:00 AM – 6:00 PM
Saturday: By Appointment
Phone
(312) 555-0180225 W Wacker Dr, Chicago
Ready to Work With Chicago's Best?
Schedule a free, no-obligation consultation with one of our attorneys. We'll discuss your legal needs, explain your options, and show you why 500+ businesses trust Sterling & Associates.