Chicago is one of the most sophisticated legal markets in the United States. As a major financial, corporate, healthcare, transportation, real estate, and litigation hub, the city is home to national law firms, elite trial lawyers, white-collar defense attorneys, plaintiff advocates, appellate lawyers, and highly focused boutique practices. For clients, that depth is both an advantage and a challenge. There are many capable Chicago attorneys, but the right lawyer depends heavily on the type of matter, the stakes involved, and the lawyer’s experience with similar cases.

This list of the top 10 best lawyers in Chicago is based on publicly available indicators such as practice focus, professional background, peer recognition, directory listings, leadership roles, major case experience, and law firm reputation. It is not a guarantee of results, and it should not be read as the only list of excellent lawyers in Chicago. Instead, it is an editorial guide to respected attorneys across several major practice areas.

1. Robert A. Clifford

Law firm: Clifford Law Offices
Main practice areas: Personal injury, aviation litigation, medical malpractice, mass torts, wrongful death

Robert A. Clifford is one of the most recognized plaintiff trial lawyers in Chicago. As the founder and senior partner of Clifford Law Offices, he has built a career around complex personal injury, aviation, medical malpractice, mass tort, and wrongful death litigation. His firm describes him as a nationally recognized Chicago-based personal injury and medical malpractice lawyer, and Clifford Law Offices has been ranked by Best Law Firms in several practice areas, including aviation.

Clifford’s reputation is also supported by peer recognition. His firm biography states that he was ranked the number-one lawyer in Illinois by Super Lawyers in 2026, a distinction he has held for multiple years. He is considered one of the best lawyers in Chicago for catastrophic injury and aviation-related cases because his practice combines trial experience, firm resources, and a long record in high-stakes plaintiff litigation.

2. Dan K. Webb

Law firm: Winston & Strawn LLP
Main practice areas: Trial practice, commercial litigation, white-collar defense, internal investigations

Dan K. Webb is one of Chicago’s best-known trial lawyers. He is co-executive chairman of Winston & Strawn and has tried more than 100 jury cases across a wide range of claims. Chambers describes him as one of the most distinguished and sought-after trial lawyers in the United States, and his firm notes that he is a Fellow of the American College of Trial Lawyers.

Webb’s background includes both public service and private litigation. His experience includes major criminal, commercial, and corporate disputes, making him a strong choice for clients facing business-critical litigation or government-facing matters. Among top lawyers in Chicago, Webb stands out for courtroom experience at the highest level.

3. Patricia Brown Holmes

Law firm: Riley Safer Holmes & Cancila LLP
Main practice areas: Commercial litigation, white-collar defense, internal investigations, crisis management, ESG counseling

Patricia Brown Holmes is a leading Chicago litigator and the managing partner of Riley Safer Holmes & Cancila. Her practice focuses on high-stakes commercial disputes, class actions, investigations, white-collar criminal defense, ESG matters, diversity audits, and crisis management counseling. Her firm biography also notes that she is the first Black woman to lead and have her name on the door of a major law firm that is not women- or minority-owned.

Chambers lists Holmes as an Eminent Practitioner in Illinois white-collar crime and government investigations. She is considered one of the best attorneys in Chicago for clients who need judgment, discretion, and litigation strategy in sensitive corporate matters.

4. Anton R. Valukas

Law firm: Jenner & Block LLP
Main practice areas: White-collar defense, civil litigation, corporate investigations, class actions, government controversies

Anton R. Valukas, often known as Tony Valukas, is a senior partner at Jenner & Block and a former United States Attorney. His practice focuses on major civil litigation, white-collar criminal litigation, contested proceedings, corporate investigations, and government-related disputes. Chambers describes him as a highly respected litigator with experience in commercial and criminal trial proceedings as well as major internal investigations.

Valukas is also a Fellow of the American College of Trial Lawyers. His public background includes high-level public service and work for major corporate and public-entity clients. He is one of the strongest names among Chicago attorneys for complex investigations and white-collar litigation.

5. Mark R. Filip

Law firm: Kirkland & Ellis LLP
Main practice areas: Government enforcement defense, internal investigations, white-collar defense, regulatory litigation

Mark R. Filip brings an unusually strong public-service background to private practice. Kirkland & Ellis states that he is a former federal judge and high-ranking Justice Department official who helps lead the firm’s government enforcement defense and internal investigations group. The U.S. Department of Justice identifies him as the 33rd Deputy Attorney General of the United States, serving from March 2008 to February 2009.

Chambers describes Filip as a renowned white-collar attorney who is frequently called on by household-name companies for complex, high-stakes FCPA investigations. For corporations, boards, and executives facing enforcement risk, Filip is one of the best lawyers in Chicago to consider.

6. Gary Feinerman

Law firm: Latham & Watkins LLP
Main practice areas: Commercial litigation, appellate litigation, constitutional law, intellectual property disputes, high-stakes civil litigation

Gary Feinerman is a former federal district judge and former Solicitor General of Illinois. Latham & Watkins states that he represents clients in high-stakes litigation and serves as Co-Chair of the Chicago office’s Litigation & Trial Department.

Chambers ranks Feinerman in Illinois general commercial litigation and notes that he draws on his experience as a former federal district judge and state solicitor general to handle a broad spectrum of litigation. He is a strong choice for complex civil disputes where legal strategy, judicial insight, and appellate framing matter.

7. Todd S. Pugh

Law firm: Breen & Pugh
Main practice areas: Criminal defense, federal criminal cases, state criminal cases, professional responsibility defense, forensic evidence

Todd S. Pugh is a leading Chicago criminal defense attorney and managing partner of Breen & Pugh. The National Association of Criminal Defense Lawyers identifies him as managing partner of the firm and notes that the firm focuses on federal and state criminal defense, professional responsibility defense, and selective civil matters.

NACDL also notes that Pugh has received national attention for trial skills and that Leading Lawyers has listed Thomas Breen and Todd Pugh among the ten best criminal defense lawyers in Illinois since 2012. For clients facing serious criminal charges, especially matters involving forensic or expert-witness issues, Pugh is one of the top lawyers in Chicago.

8. Kathleen T. Zellner

Law firm: Kathleen T. Zellner & Associates
Main practice areas: Wrongful convictions, civil rights, post-conviction litigation, medical malpractice

Kathleen T. Zellner is a nationally known attorney associated with wrongful conviction and post-conviction litigation. While her firm is based in the Chicago area rather than downtown Chicago, her profile is significant enough to include in a broader Chicago legal market discussion. Concordia University describes Zellner as a lawyer known for her work on wrongful conviction cases and commitment to justice.

Her public profile is tied to civil rights litigation, prisoner rights, medical malpractice, and post-conviction advocacy. She is a strong example of a lawyer whose reputation is built not only on litigation ability but also on persistence in difficult innocence and civil rights cases. Readers searching for the best attorney in Chicago for post-conviction or wrongful conviction matters will often encounter Zellner’s name.

9. Joseph A. Power Jr.

Law firm: Power Rogers LLP
Main practice areas: Personal injury, medical malpractice, wrongful death, trucking accidents, product liability

Joseph A. Power Jr. is a prominent Chicago plaintiff trial lawyer and founding partner of Power Rogers. Public profiles describe him as an award-winning trial lawyer with decades of experience representing individuals and families in catastrophic injury, medical malpractice, wrongful death, and transportation safety cases.

Power Rogers reports that Power has obtained more than 200 jury verdicts and settlements over $1 million, including a $55.4 million medical malpractice jury verdict and a $100 million trucking case recovery connected to the Illinois “licenses-for-bribes” scandal. His record places him among the best lawyers in Chicago for serious personal injury and wrongful death litigation.

10. William Choslovsky

Law firm: Taft Stettinius & Hollister LLP
Main practice areas: Commercial litigation, restructuring, bankruptcy-related litigation, business disputes

William Choslovsky is a Chicago litigator and restructuring lawyer with more than 25 years of experience. Taft describes him as both an accomplished litigator and restructuring lawyer who is trial-tested but also focused on solving matters outside the courtroom when possible.

Super Lawyers lists Choslovsky as a top-rated general litigation attorney in Chicago, with additional work in business bankruptcy, and notes his Super Lawyers recognition across multiple years through 2026. He is a practical choice for business clients facing commercial disputes, distressed-company issues, or litigation connected to financial pressure.

How to Choose the Best Attorney in Chicago

The phrase “best attorney in Chicago” means different things depending on the legal issue. A corporate investigation, a catastrophic injury case, a criminal charge, and a business dispute all require different skills. Before hiring a Chicago lawyer, focus on fit rather than fame.

Start with the practice area. A lawyer known for aviation litigation may not be the right choice for a white-collar defense matter. A top criminal defense attorney may not be the best option for a corporate transaction or estate dispute.

Next, check experience with similar matters. Ask whether the lawyer has handled cases like yours, what strategy they would consider, and what risks they see. Good lawyers do not promise guaranteed outcomes. They explain the path, the uncertainty, and the cost.

You should also consider resources. Some cases require a large team, expert witnesses, forensic analysis, document review, or regulatory knowledge. Other matters may be better handled by a focused boutique firm.

Finally, pay attention to communication. The best Chicago attorneys are usually direct about fees, timelines, strengths, weaknesses, and realistic expectations.

FAQs About Hiring Lawyers in Chicago

Who is the best lawyer in Chicago?

There is no single best lawyer for every legal issue. The best lawyer depends on your matter. For example, Robert Clifford and Joseph Power Jr. are highly recognized in plaintiff injury litigation, while Dan Webb, Patricia Brown Holmes, Anton Valukas, and Mark Filip are known for complex commercial, white-collar, and investigation work.

How much does a Chicago attorney cost?

Fees vary widely. Personal injury lawyers often work on contingency, meaning they are paid from a recovery if the case succeeds. Business litigation, criminal defense, white-collar matters, and corporate work are often billed hourly or by negotiated fee arrangement. Always ask for a written fee agreement.

Should I hire a large Chicago law firm or a boutique firm?

It depends on the case. Large law firms may be better suited for corporate investigations, major commercial litigation, or multi-jurisdiction disputes. Boutique firms can be excellent for criminal defense, plaintiff litigation, family law, estate litigation, and specialized matters where senior-lawyer attention is critical.

Are lawyer rankings reliable?

Rankings from Chambers, Best Lawyers, Super Lawyers, and similar directories can be useful, but they are not the whole story. They should be used as a starting point alongside consultations, case fit, availability, fees, and client comfort.

What should I ask before hiring a Chicago lawyer?

Ask about similar case experience, likely strategy, expected timeline, fee structure, who will work on the matter, and what risks could affect the outcome. A trustworthy attorney should answer clearly and avoid exaggerated promises.

Conclusion

Chicago has a deep and competitive legal market, with attorneys handling some of the country’s most important trials, investigations, injury cases, business disputes, and criminal defense matters. The lawyers listed above represent a cross-section of respected legal talent across major practice areas.

The right Chicago attorney is not simply the most famous name. It is the lawyer whose experience matches your legal issue, whose communication style works for you, and whose judgment you trust when the stakes are high. Before hiring any lawyer, review credentials, compare practice focus, schedule a consultation, and make sure the attorney has the right background for your specific legal needs.