Will AI Replace Legal Jobs in Chicago? Here’s What to Do in 2025

Chicago lawyers should care because 2025 saw a wave of state AI action - the National Conference of State Legislatures documents every state introducing AI bills and dozens enacting measures this year - and Illinois has drawn a bright legal line around health and consumer-facing uses of AI: the new Wellness and Oversight for Psychological Resources Act bars AI from delivering therapy and authorizes civil penalties (reports note fines up to $10,000 and enforcement by IDFPR), while other Illinois proposals (e.g., HB3529) would require business AI governance disclosures; see the NCSL 2025 State AI Legislation Summary (NCSL 2025 State AI Legislation Summary), the Illinois prohibition on AI therapy - Nixon Peabody enforcement alert (Illinois prohibition on AI therapy - Nixon Peabody alert), and practical training options to upskill teams.

The immediate takeaway for Chicago firms: audit client-facing tools, tighten consent and marketing language, and train staff on safe AI workflows - practical skills taught in Nucamp's AI Essentials for Work bootcamp can accelerate compliance and risk reduction; see the Nucamp AI Essentials for Work 15-week syllabus (Nucamp AI Essentials for Work 15-week syllabus) and the Nucamp AI Essentials for Work registration page (Nucamp AI Essentials for Work registration).

Bootcamp: AI Essentials for Work - Length: 15 Weeks - Early Bird Cost: $3,582 - Registration: Register for AI Essentials for Work.

AI can accelerate routine legal tasks for Chicago firms - fast document search, first-draft pleadings, and large-scale eDiscovery triage - but it cannot replace the lawyer who frames the facts, probes gaps, or vets authority: Illinois practitioner Michael Helfand reports callers weekly who relied on AI and “got almost everything wrong,” and leading benchmarks show persistent hallucinations that matter in court.

A Stanford HAI study found even purpose-built legal AIs returned incorrect or misgrounded results at alarming rates (Lexis+ and Ask Practical Law >17%; Westlaw's AI >34%), and broader tests of general chatbots showed far higher error rates on legal queries.

So what? Every AI-generated proposition and citation needs lawyer verification before filing or client advice, because the time spent checking hallucinations can erase promised efficiency gains and create malpractice exposure under Illinois rules.

Treat models as high-speed assistants for retrieval and drafting, not authoritative decision-makers, and build mandatory verification steps into firm workflows - start with tool-specific checklists and a requirement that a licensed attorney confirm any case law or statutory interpretation before use (see Stanford HAI and Helfand for evidence and examples).

But the bigger issue as far as I've seen is that AI relies on you to present all of the relevant facts and can't be counted on to ask things ...

Illinois has moved from guidance to enforceable rules, signaling the practical risk Chicago lawyers must manage: the state's new Wellness and Oversight for Psychological Resources Act bars AI from delivering therapy, expands confidentiality for behavioral‑health records, and authorizes the Illinois Department of Financial and Professional Regulation to impose civil penalties (reports note fines up to $10,000 per violation) - see the Nixon Peabody alert: Illinois AI therapy prohibition (Nixon Peabody alert on Illinois prohibition against AI therapy) and a detailed briefing on enforcement and compliance by Baker Donelson (Baker Donelson briefing on Illinois AI regulation in behavioral health).

At the same time Illinois lawmakers are advancing disclosure and governance bills (e.g., HB3529) while the National Conference of State Legislatures documents that all 50 states introduced AI bills in 2025 and dozens adopted measures this year - a clear signal that transparency, impact assessments, and human‑in‑the‑loop requirements are becoming baseline expectations for legal work and client advice (NCSL 2025 state AI legislation summary and analysis).

So what? Chicago firms must treat AI use as a regulatory compliance issue: update intake and consent language, geofence or disable therapeutic features for Illinois clients, and add vendor audit clauses to contracts to avoid fines and enforcement exposure.

Chicago firms must treat AI adoption as a potential labor event: Illinois' WARN rules require employers with 75 or more full‑time employees to give 60 days' notice for plant closures or mass layoffs, so automation‑driven restructurings can trigger formal WARN obligations (Illinois WARN - 60‑day notice for employers with 75+ employees); at the same time Illinois' H.B. 3773 makes use of AI that has a discriminatory effect unlawful and requires notice when AI is used in hiring, promotion, discipline, or discharge (effective Jan.

1, 2026), meaning transparency obligations now overlay traditional labor law risks (Illinois H.B. 3773 - AI restrictions and notice requirements in HR).

Unions are already negotiating AI safeguards and bargaining over implementation terms - early engagement, clear notice, upskilling and recall/severance language can avoid strikes or unfair‑labor‑practice claims, per labor‑response playbooks for employers (Labor response to AI - union bargaining examples and employer guidance).

So what? If AI changes duties, hours, surveillance, or headcount, plan for bargaining, WARN timelines, and written AI‑use notices as part of any rollout to reduce legal and operational disruption.

Key rules and practices to track:

• Illinois WARN: Applies to employers with 75+ full‑time employees; 60 days advance notice required for plant closures and mass layoffs.
• H.B. 3773 (Illinois): Makes it unlawful to use AI that has a discriminatory effect in hiring, promotion, discipline, or termination; requires notice to applicants and employees (effective Jan. 1, 2026).
• Union/collective bargaining agreements (CBAs): Unions are negotiating AI protections (notice, severance, recall, consent/consultation); employers should engage early and document agreements to reduce dispute risk.

Turn regulatory risk into repeatable practice: begin with a tool inventory and a written, tool‑specific risk assessment that flags any “self‑learning” models and confirms whether client data will train vendor systems (follow ABA Formal Opinion 512's advice on competence and confidentiality - ABA Formal Opinion 512 guidance for using generative AI in legal practice); next, update engagement letters and intake scripts to describe AI use and fee treatment, obtain informed client consent before inputting client data, and document disclosures that affect fees or decision‑making (Clio's Legal Trends materials show clients expect transparency and that AI changes billing dynamics - Clio 2024 Legal Trends Report on AI and client billing expectations).

Require a one‑line verification checklist for every AI output used in advice or filings (licensed‑attorney signoff for citations/statutory interpretation), run vendor audits and vendor‑contract confidentiality clauses, and deliver mandatory, role‑based training plus written supervisory policies so managers satisfy Model Rules 5.1/5.3.

Finally, coordinate with HR on WARN timelines and H.B. 3773 notice obligations before any automation that changes headcount or hiring processes; these steps make AI adoption defensible, auditable, and client‑friendly, not just faster.

“I remain both excited and optimistic about how generative AI can transform the legal profession. Just as other technologies have entered our space over the years - like computers, the internet, email, and cloud computing - we're going to have to start with education. The ISBA and other bar associations are well‑positioned to foster awareness and education of responsible and ethical adoption of AI technologies in the legal profession. Bar associations can and should be an intermediary between legal tech companies developing novel tools and applications and the legal professionals using them.”

Chicago attorneys should prioritize practical, skills‑based training that mirrors how legal AI is actually built and governed: the University of Chicago Law School's new AI Lab (launching fall 2025) will have students assemble meticulously researched legal summaries and put them into a generative system to produce a renter‑rights chatbot released to the public - an example of turning classroom work into deployable legal tech (University of Chicago Law AI Lab course details); meanwhile, Chicago‑Kent's faculty-led Law Lab and its J.D. Certificate in Legal Innovation + Technology teach the polytechnic mix of NLP, legal analytics, and product‑minded practice that makes verification protocols and vendor‑safe RAG (retrieval‑augmented generation) workflows usable in firm settings (Chicago‑Kent Law Lab and Legal Innovation + Technology program details).

For firms planning tuition support or recruiting pipelines, review formal funding and scholarship options to subsidize this upskilling (University of Chicago Law scholarships and financial aid information).

So what? Hiring or partnering with graduates who have built and tested domain models and verification steps lets firms bypass early experimentation and adopt auditable AI practices faster, reducing exposure to hallucinations and regulatory gaps.

“AI is like putty; you have to play with it to understand it. The AI Lab is an opportunity for students to play in the sandbox of AI, to get hands‑on experience with the defining technology of our age.”

Managing AI risk in Illinois means treating every model output as unvetted evidence: verify every citation and factual claim against primary sources, run periodic vendor audits, and document a licensed‑attorney sign‑off before filing or advising clients to avoid malpractice exposure.

The Illinois Supreme Court's recent policy and judicial reference sheet make clear that existing ethics rules apply and judges expect parties to review AI‑generated content, so keep an auditable trail of prompts, tool versions, and verification steps and add vendor contract clauses that prohibit training on client data; see the Illinois Supreme Court AI policy (Dec.

2024) for details: Illinois Supreme Court AI policy (December 2024).

Real‑world sanctions are no longer hypothetical: Illinois appellate discipline has already penalized counsel for unverified AI citations (e.g., In re Baby Boy required returning $6,925.62 to the county and a $1,000 fine plus disciplinary referral), underlining the “so what?” - insufficient verification can cost firms real dollars, reputation, and bar complaints; see the Illinois appellate court report on AI sanctions: Illinois appellate court AI sanctions report and analysis.

Practical controls: mandatory verification checklists, periodic CLE on AI competence, documented vendor audits, and retention of native AI outputs for discovery and malpractice defense.

"Courts must do everything they can to keep up with this rapidly changing technology. This policy recognizes that while AI use continues to grow, our current rules are sufficient to govern its use. However, there will be challenges as these systems evolve and the Court will regularly reassess those rules and this policy."

Future scenarios in Chicago point to augmentation rather than wholesale replacement: targeted automation - predictive coding for eDiscovery and fast drafting tools - will shrink routine document‑review headcount while expanding short‑term, project‑based gigs and demand for technical expertise, legal‑operations, and oversight roles that verify AI outputs; firms that recruit or train attorneys with demonstrable legal‑tech skills will be better positioned in this shift, because clients and in‑house teams increasingly expect tech fluency (see the 2025 recruitment trends on emphasis for legal tech and contract roles at BCGSearch - BCGSearch law firm recruitment trends 2025).

Concurrently, sustained investment is likely - legal departments plan larger legal‑tech budgets - which makes time‑boxed pilot teams and vendor‑audit roles a practical path to scale while preserving attorney verification steps (Legal Tech Connection legal‑tech budget outlook 2025).

The net effect: expect fewer pure entry‑level review jobs, more contract/project work, and rising hiring premiums for candidates who can manage retrieval‑augmented generation, audits, and model verification - echoing broader expert concerns about displacement and new oversight work in the Elon University survey (Elon University 2025 survey on AI and robotics impacts) - so Chicago practices should map which roles will be automated, which must be human‑verified, and where to invest in upskilling now.

“legal work will be more interesting.”

Practical resources and a short checklist let Chicago lawyers turn regulatory uncertainty into repeatable compliance: track live state action with the NCSL 2025 artificial intelligence legislation summary to spot Illinois bills (HB3529, S‑1366, S‑2203) and nationwide trends (NCSL 2025 artificial intelligence legislation summary), review the NCSL AI and law enforcement federal and state landscape brief for specific limits on facial recognition and drones that affect evidence and surveillance practices (NCSL AI and law enforcement: federal and state landscape), and pick a short, tool‑focused upskilling path or pilot (use the Nucamp Top‑10 tools guide or a 15‑week AI Essentials syllabus) to build verification workflows and vendor audits before scaling (Nucamp AI Essentials for Work syllabus (15 Weeks)).

Checklist headline: inventory tools, require a dated one‑line attorney verification attached to every AI‑assisted filing, document vendor training/data use, and run quarterly vendor audits - do this and a single failed verification becomes a trainer, not a malpractice crisis.

“To maintain global leadership in AI, America's private sector must be unencumbered by bureaucratic red tape.”

Chicago legal teams should treat 2025 as the year to turn AI uncertainty into a defensible playbook: inventory every tool, lock vendor contracts against training on client data, add mandatory attorney sign‑off for any AI‑generated citation, and update engagement letters and intake scripts to disclose AI use - because Illinois has moved from guidance to enforcement (the WOPR law bans AI therapy and enforcement actions can include civil penalties), and state trends tracked by the NCSL 2025 AI Legislation Summary for States show disclosure, impact assessments, and human‑in‑the‑loop rules becoming baseline expectations; firms that pair those controls with a short, practical upskilling program (for example, the Nucamp AI Essentials for Work 15‑Week Syllabus) will both reduce malpractice exposure and capture verified productivity gains while meeting Illinois enforcement realities (see the Illinois AI Therapy Law Press Release (IDFPR)).

“The people of Illinois deserve quality healthcare from real, qualified professionals and not computer programs that pull information from all corners of the internet to generate responses that harm patients.”