Skip to main content
Posted June 13, 2026

Legal - Litigation Attorney II-III

Cincinnati Insurance Companies
Chicago, IL Full Time
Compensation: $120,000 to $170,000 Annually
Reference: CincinnatiInsuranceCompanies2600511

Make a difference with a career in insurance

At The Cincinnati Insurance Companies, we put people first and apply the Golden Rule to our daily operations. To put this into action, we’re looking for extraordinary people to join our talented team. Our service-oriented, ethical, knowledgeable, caring associates are the heart of our vision to be the best company serving independent agents. We help protect families and businesses as they work to prevent or recover from a loss. Share your talents to help us reach for continued success as we bring value to the communities we serve and demonstrate that Actions Speak Louder in Person®.

If you’re ready to build productive relationships, collaborate within a diverse team, embrace challenges and develop your skills, then Cincinnati may be the place for you. We offer career opportunities where you can contribute and grow.

Build your future with us

Our Legal-Litigation department seeks an experienced worker's compensation attorney for our Chicago, Illinois, location.

The pay range for this position is $120,000 - $170,000 annually. Pay is based on the applicant's education, experience, location, knowledge, skills and abilities. Eligible associates may also receive an annual cash bonus and stock incentives based on company and individual performance.

Be ready to:

  • Represent employers and insurance carriers in all aspects of workers’ compensation matters.
  • Manage cases from inception through resolution, including hearings and appeals.
  • Investigative facts and provide legal advice to clients.
  • Conduct legal research, draft and file pleadings, motions, and briefs.
  • Appear before the Illinois Workers’ Compensation Commission (IWCC).
  • Take and defend depositions, including expert and fact witnesses.
  • Prepare for, and attend pre-trials, arbitrations, hearings, and trials.
  • Conduct post-trial activities, including Commission Appeals, Circuit Court, and Appellate Court Appeals.
  • Communicate effectively with clients, adjusters, and opposing counsel.
  • Provide strategic legal advice and case evaluations to litigation claims supervisors.

Be equipped with:

  • Illinois law license with 5 or more years of legal experience in the workers’ compensation area.

  • Knowledge of the insurance industry claims and the worker’s compensation legal environment.
  • Experience taking worker’s compensation matters to final hearings and trials, and handling appeals to the Commission, trial courts, and courts of appeals.
  • Demonstrated case analysis skills and a track record of proven trial and negotiation skills.
  • Strong analytical skills, excellent oral and written communication skills, proactive approach to file handling and caseloads.
  • Ability to work independently and as well as within a team environment.
  • Strong computer skills including use of Lexis or Westlaw and computer-based case management systems.

Enhance your talents

Providing outstanding service and developing strong relationships with our independent agents are hallmarks of our company. Whether you have experience from another carrier or you’re new to the insurance industry, we promote a lifelong learning approach. Cincinnati provides you with the tools and training to be successful and to become a trusted, respected insurance professional – all while enjoying a meaningful career.

Enjoy benefits and amenities

Your commitment to providing strong service, sharing best practices and creating solutions that impact lives is appreciated. To increase the well-being and satisfaction of our associates, we offer a variety of benefits and amenities. Learn more about our benefits and amenities packages.

Embrace a diverse team

As a relationship-based organization, we welcome and value a diverse workforce. We grant equal employment opportunity to all qualified persons without regard to race; creed; color; sex, including sexual orientation; gender identity and transgender status; religion; national origin; age; disability; military service; veteran status; pregnancy; AIDS/HIV or genetic information; or any other basis prohibited by law. Learn more about the Federal Employment Notices.

Sign up for Job Alerts