Paralegal Jobs in Chicago, IL
Paralegal jobs in Chicago are in strong demand, concentrated in the Loop, River North, and the Civic Center corridor across corporate law, real estate, and litigation practices. Leading employers hiring right now include Jobot, Katten, and CIP. Find a role that fits below and apply directly.
Find Paralegal JobsOverview
Showing 5 of 101+ Paralegal jobs







Hennessy & Roach, P.C. is a law firm defending employers in Workers’ Compensation and defendants in General Liability matters. H&R is based in Chicago with additional offices in Springfield, Illinois; St. Louis, Missouri; Overland Park, KS; Milwaukee, Wisconsin; Indianapolis, Indiana; Brentwood, Tennessee; and Omaha, Nebraska. The firm handles matters throughout the States of Illinois, Indiana, Iowa, Missouri, Nebraska, Kansas, Tennessee, and Wisconsin. Founded by Thomas G. Hennessy and James P. Roach on May 17, 1993, the firm continues to grow.
Job Description
Successful law firm seeks a full time Paralegal for our Chicago, IL location. Candidate must possess excellent organizational skills and have comprehensive experience with the legal profession. This position requires a highly motivated, organized professional capable of functioning in a fast-paced, challenging legal environment. Scheduled hours may be either 8:00am – 4:00pm or 9:00am – 5:00pm.
The Paralegal role enhances attorneys’ effectiveness by developing case information, evidence, and settlement options, tracking cases, and supporting attorneys’ hearing proceedings. This position will support multiple attorneys with the preparation of documents for general liability cases. Paralegal will bill hours to client.
Essential Job Functions:
- Assists attorneys in preparation for hearings and trials. Assists in preparing legal documents such as legal arguments, motions, contracts, and agreements.
- Investigates and fact-finds for cases. Identifies relevant legal articles, laws, and judicial decisions for cases. Cross-checks and validates information.
- Keeps cases organized by establishing, organizing, tracking, and maintaining files; monitoring calendars; meeting deadlines; documenting actions; inputting information into file database and case management software.
- Helps develop cases by maintaining contact with people involved in the case, scheduling depositions, assisting with discovery requests and responses, requests medical records, scheduling IMEs, preparing, and filing pleadings.
- Enhances hearing preparations and proceedings by organizing evidence, preparing exhibits, scheduling witnesses, ensuring that witnesses are ready when needed.
- Transcribes dictation, completes daily mailings, maintains firm calendar, and coordinates court appearances and out of town travel.
- Accomplishes organization goals, accepts new and different requests, and explores opportunities to add value to efficiency and effectiveness of job responsibilities.
- Monitors and reviews government regulations.
- Monitor billable hours and submit hours in Perfect Law software.
- Other related duties as assigned.
Qualifications
- Paralegal certificate required. Certification from the National Association of Legal Assistants (NALA) or the American Alliance Certified Paralegal (AACP) credential offered by the American Alliance of Paralegals, Inc. is highly preferred.
- Associate degree or bachelor's degree preferred.
- 1 - 2+ years of Legal Assistant or Paralegal experience supporting a legal office.
- Working knowledge of legal principles and practices. In-depth knowledge of local, state, and federal laws and regulations.
- Thorough knowledge of legal research techniques and legal terminology.
- Microsoft Word experience required; Excel and PowerPoint experience preferred. Perfect Law legal software experience preferred.
- Outstanding organizational, interpersonal, research and administrative skills.
- Excellent attention to detail with the ability to multi-task.
- Excellent telephone, writing, and proofreading skills.
- Must be self-motivated and able to meet deadlines under pressure.
- Must be able to work as part of a team, and also independently.
- Organization, Planning, Attention to Detail, and Dependability.
- Firm and Client Confidentiality required.
Additional Information
Benefits include: Medical, Dental, Vision, Group Term Life Insurance, Voluntary Term Life Insurance, Critical Illness, Accident, HSA, FSA, pre-tax Transit and pre-tax Parking. 401(k)/Roth retirement plan with company match. Generous time off policy.
All your information will be kept confidential according to EEO guidelines.
See All 101+ Paralegal Jobs in Chicago
Find roles in Chicago that match your experience and apply in just a few clicks.
Find Paralegal JobsParalegal Job Market in Chicago
Who's Hiring



Top Industries Hiring
- Law & Legal Services
- Staffing & Recruiting
- Technology & Software
- Marketing & Advertising
- Construction & Real Estate
Paralegal Jobs in Chicago: Frequently Asked Questions
How do I get a paralegal job in Chicago?
Focus your search on the Loop and River North, where large law firms, financial institutions, and corporate legal departments concentrate most of their hiring. Chicago's dense base of AmLaw 100 firms, insurance companies, and real estate developers creates steady demand, particularly in litigation, transactional, and compliance work. Candidates with e-discovery experience or a specialty in corporate or real estate law tend to stand out in this market.
Which companies hire paralegals in Chicago?
Companies currently hiring paralegals in Chicago include Jobot, Katten, and CIP, per current listings on Migrate Mate as of November 2026. Chicago's hiring mix leans heavily toward large law firms, financial services firms, and healthcare systems, all of which maintain substantial in-house legal teams alongside outside counsel.
Are there remote paralegal jobs in Chicago?
Yes, though remote availability depends on the role: document review, research, and contract management work is more remote-friendly than litigation support or court-filing roles that require physical presence. About 71% of paralegal openings tied to Chicago are remote or hybrid as of November 2026. Corporate and compliance-focused positions at Chicago-based financial and insurance firms tend to offer the most flexible arrangements.
How can I get a paralegal job in Chicago with little or no experience?
The most realistic entry path in Chicago is landing a legal assistant or paralegal coordinator role at a mid-size Loop firm or a Chicago-area insurance company, where on-the-job training is common. Chicago's large healthcare systems and municipal agencies also hire entry-level paralegals and legal support staff. A certificate from one of Chicago's ABA-approved programs, such as those offered at DePaul or Roosevelt, carries real weight with local employers who recruit directly from those pipelines.
Which industries hire the most paralegals in Chicago?
The sectors hiring the most paralegals in Chicago are Law & Legal Services, Staffing & Recruiting, and Technology & Software, based on current listings on Migrate Mate as of November 2026. Chicago's role as a national hub for finance, commercial real estate, and healthcare drives outsized demand compared to most other metro areas, keeping paralegal hiring active across both law firms and in-house legal teams.
Related Jobs in Illinois
See All 101+ Paralegal Jobs in Chicago
Find roles in Chicago that match your experience and apply in just a few clicks.
Find Paralegal Jobs