Top 10 AI Tools Every Legal Professional in Chicago Should Know in 2025

Chicago firms face a practical inflection point in 2025: AI is already proven to speed routine work - freeing roughly four hours per lawyer each week and, per industry modeling, translating into about $100,000 in potential new billable value annually - so firms that ignore it risk losing efficiency and revenue Thomson Reuters analysis on AI transforming the legal profession (2025).

At the same time, a Forrester‑modeled Lexis+ scenario found widescale in‑house AI use could reduce work sent to outside counsel by up to 13%, a concrete pressure point for Chicago practices that handle high-volume litigation, contract review, and regulatory matters LexisNexis/Forrester study on AI reducing outside counsel work (2025).

That “efficiency paradox” changes client expectations and billing ethics - requiring transparent fee conversations and human-in-the-loop safeguards.

Proactive training matters: the 15-week AI Essentials for Work bootcamp offers practical, nontechnical skill-building and a ready syllabus to get legal teams started - AI Essentials for Work bootcamp syllabus (Nucamp).

Selection prioritized practical safeguards and local fit: each candidate had to publish clear, auditable training or syllabus material (evaluated against an academic course‑catalog model like Ripon College's Ripon College course catalog overview), demonstrate human‑in‑the‑loop controls to

prevent AI hallucinations from becoming legal headaches

(human-in-the-loop policies for legal AI deployment), and show concrete client-facing outputs such as plain‑English case summaries for Chicago clients (plain‑English case summaries for Chicago clients).

Criteria also weighed vendor transparency (audit logs, data handling), demonstrable time‑savings on routine tasks, and ease of piloting within a mid‑sized Chicago firm so teams can validate results locally before scaling - an approach designed to balance efficiency gains with Illinois ethical and malpractice risk management.

RelativityOne's aiR suite (aiR for Review) puts generative‑AI‑driven, human‑supervised eDiscovery into practical use for Illinois litigators by automating first‑pass relevance, issue tagging, and key‑document identification while producing transparent rationales and document citations that aid QC and defensibility; reviewers write Prompt Criteria, validate predictions against human‑coded samples, then scale validated prompts to large sets - Relativity advertises “review in hours, not days” and case examples such as 1M documents processed in 18 days show the scale potential.

aiR runs on Azure OpenAI (GPT‑4 Omni in the U.S.), with Relativity and Microsoft stating that submitted data is not retained beyond a customer's instance, a notable point for Chicago firms weighing data residency and malpractice risk.

Recent RelativityOne updates raised job limits (up to 250,000 documents) and report up to 3x faster job performance, making aiR a practical pilot for mid‑sized firms that want measurable time‑savings, auditable outputs, and human‑in‑the‑loop controls before wider deployment; see the official aiR for Review documentation and Relativity's product overview for setup, validation workflows, and security details.

Region	Current LLM Model	Deployment Date	aiR Version
United States	GPT-4 Omni - November	2025-06-16	2025.06.1

It uses generative artificial intelligence (AI) to simulate the actions of a human reviewer by finding and describing relevant documents according to the review instructions (Prompt Criteria) that you provide.

CoCounsel (formerly Casetext's Co‑Counsel, now part of Thomson Reuters) packages deep legal research, document analysis, and drafting into a single, Westlaw‑backed workflow that matters for Illinois practitioners: it connects Westlaw and Practical Law state resources to Microsoft Word so teams can draft, embed Westlaw KeyCite flags, and verify Illinois statutes and appellate decisions without context‑switching - helpful when a mid‑sized Chicago firm needs a fast, auditable check before court filings or client memos.

Built for human‑in‑the‑loop use, CoCounsel advertises measurable gains - 2.6x faster document review and drafting and broad adoption across U.S. federal users and large firms - so the practical payoff is fewer billable hours lost to rote work and more time for strategy and client counseling; explore the product details at the CoCounsel legal product page and read early coverage of the Casetext CoCounsel launch for implementation notes.

Metric	Value
Document review / drafting speed	2.6x
Users finding more key information	85%
Organizations likelier to grow with AI strategy	2x

“CoCounsel is truly revolutionary legal tech. Its power to increase our attorneys' efficiency has already benefited our clients. And we have only scratched the surface of this incredible technology.” - John Polson, Fisher Phillips

Westlaw Edge bundles authoritative primary and secondary content with AI tools that matter for Illinois practice: upload a brief to Quick Check and, in minutes, it will flag bad law, surface contrary authority, and - with the new Mischaracterization Identification enhancement - explain why a quotation or context may be misleading (Westlaw Edge Quick Check Mischaracterization Identification announcement); use AI Jurisdictional Surveys to spin up Illinois‑specific surveys quickly, run WestSearch Plus for AI‑enhanced search results grounded in Westlaw content, and rely on Litigation Analytics to size damages and weigh a judge's tendencies so settlement posture and motion strategy are evidence‑driven (Westlaw Edge Litigation Analytics product page).

KeyCite and KeyCite Overruling Risk surface implicit negative treatment so attorneys can verify citations before filing, and Thomson Reuters emphasizes human verification and attorney‑editor oversight to keep AI outputs defensible (Westlaw Edge features and AI-assisted research overview).

The practical payoff for Chicago firms: faster, auditable checks of opposing briefs plus judge‑and‑damages analytics that convert research time into clearer settlement and litigation choices.

Feature	Practical use for Illinois lawyers
Quick Check & Mischaracterization Identification	Identify bad law, contrary authority, and potential quotation mischaracterizations in briefs - results in minutes
Litigation Analytics (Damages, Judge Analytics)	Assess likely damages, judge tendencies, and timelines to inform settlement strategy
KeyCite / Overruling Risk	Flag direct and implicit negative treatment so citations are reliable in Illinois filings

“I use Quick Check for my own briefs, to give me peace of mind that I didn't miss something or that at the very least I had looked at it and made a determination. That helps me sleep at night.” - Jeunesse M. Rutledge, Associate, Reinhart Boerner Van Deuren s.c.

ChatGPT is a versatile drafting and summarization workhorse for Illinois lawyers: it can generate structured first drafts (think a demand letter for a client rear‑ended at a downtown Chicago red light), produce concise summaries of long briefs and deposition transcripts, and speed routine client communications so teams can focus on strategy; practitioners report dramatic time savings - Gavel cites drafting time cut by up to 90% - but the “so what” is this: those hours translate directly into faster client responses and more time for courtroom work, provided outputs are verified and secured.

Practical safeguards matter - use enterprise or private GPTs, redact sensitive facts, and keep a human‑in‑the‑loop to catch hallucinations and faulty citations (the free plans also have token limits like ~4,096 tokens).

For concrete prompts and examples tailored to lawyering in Chicago, see a lawyer‑focused primer on ChatGPT use cases and sample prompts from Rankings.io and a practitioner guide on practical benefits and limits from Gavel: Lawyer-focused ChatGPT use cases and sample prompts (Rankings.io) and Gavel practitioner guide to ChatGPT and Claude for lawyers (Gavel).

Top Use	Practical Payoff	Illinois Note
Drafting (demand letters, memos)	Structured first drafts that save hours	Can produce Chicago‑specific drafts (example: downtown rear‑end demand); always lawyer‑review
Summarization (briefs, transcripts)	Client‑ready summaries and action items	Speeds client updates for Illinois matters; verify citations
Legal research assist	Fast surfacing of relevant authority	Helpful start for Illinois law but requires Westlaw/KeyCite‑level verification

“Legal teams who successfully harness the power of generative AI will have a material competitive advantage over those who don't.”

Anthropic's Claude family is now a practical contender for Chicago firms that need deep document review and risk analysis: Opus and Sonnet deliver high‑precision reasoning and vision that can ingest PDFs, charts, and long deposition sets with a 200K token context - and Sonnet 4's 1M‑token beta (≈750,000 words) lets teams place an entire contract portfolio or multi‑day transcript into one prompt, reducing manual stitching and surfacing risk flags faster than paging through folders (so what: that can turn a days‑long privilege review into an actionable first pass in hours).

Claude's near‑perfect recall benchmarks, reduced hallucination rates, and structured output options (JSON, citations coming soon) support defensible human‑in‑the‑loop workflows, while cloud availability via Amazon Bedrock and Google Vertex AI helps meet U.S. data residency and deployment needs; evaluate Sonnet for scalable RAG and Opus for the highest‑complexity analysis.

Read Anthropic's model announcement and developer overview, and see coverage of Sonnet's long‑context rollout for enterprise customers for implementation notes and tradeoffs Anthropic Claude 3 family announcement, Anthropic Claude model overview and pricing, TechCrunch coverage of Sonnet 4 long‑context update.

Model	Context Window	Practical use for Illinois lawyers
Claude Opus 4.1	200K	Advanced reasoning, deep research review, high‑complexity risk analysis
Claude Sonnet 4	200K (1M beta)	Scalable RAG, multi‑document contract/dep transcript review, rapid data extraction
Claude Haiku 3.5	200K	Fast, cost‑effective summarization and triage for intake/ops

“really happy with the API business and the way it's been growing.” - Brad Abrams, Anthropic product lead

Chicago litigation teams choosing beyond the Relativity mainstream should weigh Everlaw, Nextpoint, and DISCO on three practical axes: speed, cost predictability, and ease of use.

Everlaw tops G2's summer comparisons and advertises cloud processing speeds “up to 900K documents per hour,” making it a strong choice when terabytes of ESI must be processed quickly and defensibly for FRCP productions (Everlaw vs Relativity comparison for eDiscovery processing speed and features).

Nextpoint targets smaller‑to‑mid firms with simple drag‑and‑drop ingestion, no per‑import hosting fees, and competitive per‑user economics (examples show 100 users ≈ $5,000/month in some comparisons), so it can cut pilot costs for a Chicago firm testing AI‑assisted workflows (Nextpoint eDiscovery features and pricing comparison - Jatheon market summary).

DISCO appears across industry provider lists as a fast, user‑friendly alternative with clear $/GB pricing in market comparisons - useful when budgeting for large review projects.

So what: pick Everlaw when speed and large‑scale AI review matter, Nextpoint when low‑friction onboarding and predictable per‑user pricing matter, and DISCO when a balance of speed and transparent GB pricing helps control review spend under Illinois/FRCP obligations.

Vendor	Standout point	Cost note
Everlaw	G2 leader; cloud processing up to 900K docs/hr	Pricing by quote; positioned for mid‑to‑large matters
Nextpoint	Drag‑and‑drop unlimited uploads; quick setup for smaller teams	Examples: ~100 users ≈ $5,000/month (market comparisons)
DISCO	Intuitive UI and fast processing; widely listed in provider directories	Market examples show ~$35 per GB/month pricing

"The Everlaw UI is (almost) as intuitive as Apple's products. And in the rare instances where something was confusing, the friendly and North American‑based support team was super 'on it' to help us out."

For Chicago firms facing heavy pre‑signature workloads, LawGeex's patented contract‑review AI stands out for measurable, auditable gains: a Forrester‑modeled 209% ROI and 6,500+ hours saved in contract review and negotiation, plus vendor‑reported benefits like 80% time saved, 3x faster deal closings, and substantial cost reductions - making it a practical pilot when local malpractice and data‑residency questions demand human‑in‑the‑loop checks and clear playbooks; explore LawGeex's contract review automation to see how policy‑driven redlines, clause analytics, and enterprise security fit an Illinois practice LawGeex contract review automation.

Chicago teams should also survey the broader market - contract negotiation and CLM directories map alternatives and integration patterns - before choosing a CLM strategy that meets FRCP and state‑law workflows (Contract negotiation and CLM tools overview).

Finally, require human‑in‑the‑loop policies and pilot verification so AI redlines become defensible, not risky, in Illinois matters (Nucamp AI Essentials for Work syllabus - human-in-the-loop policies for legal AI); peers to consider include Diligen, Latch, OneLaw.ai, Gavel.io, and Legaly depending on your firm's size and integration needs.

Metric	Value
Forrester Total Economic Impact (ROI)	209%
Hours saved (case studies)	6,500+ hours
Time saved reviewing/approving contracts	80%
Faster deal closing	3×
Cost saved vs. manual review	~90%

For Chicago litigators, litigation analytics are no longer optional: Lex Machina's Legal Analytics platform converts millions of court records into judge‑and‑venue intelligence - timing events, motion metrics, judge findings, counsel histories, and damages - that directly informs whether to file, remove, or press for settlement; its 2025 Patent Litigation Report even shows the Eastern District of Texas leading filings while the Northern District of Illinois sits as the next most active patent venue, a concrete “so what” for Chicago IP teams weighing venue strategy and exposure Lex Machina Legal Analytics platform and the 2025 Patent Litigation Report.

Pairing that vendor data with local judge‑research best practices - quantifying a judge's grant/denial rates or time to disposition - turns anecdote into a defensible strategic playbook for Illinois matters, as explained in an Illinois Supreme Court Review primer on legal analytics Making Sense of the Legal Analytics Revolution.

Metric	Lex Machina (selected)
Cases covered	10M+ federal cases (+state coverage)
Judges profiled	8K+ judges
Documents indexed	45M+ documents

"I use Lex Machina for every case. It's such a great resource." - John Johnson, Partner, Fish & Richardson

For Chicago firms that need reliable intake without the salary overhead, Smith.ai's hybrid AI + human model offers predictable per‑call billing (plans start at $292.50/month for 30 calls; typical per‑call pricing $6.75–$9.75 with overages around $8–$11) and features that matter locally - 24/7 North America‑based answering, bilingual agents, real‑time call summaries and transcripts, CRM/calendar integrations, payment collection, and robust spam blocking - so teams can capture after‑hours leads and free up billable time; Smith.ai's own ROI examples note that reclaiming just one hour per day across three staffers converts to roughly $1,800/month in billable work recovered, a concrete “so what” for Chicago solos and small firms balancing downtown rent and associate time.

Compare plan details and legal use cases on the Smith.ai virtual receptionist pricing guide and the Smith.ai vs. Answering Legal comparison for feature‑level tradeoffs.

Metric	Value
Starter plan	$292.50/month (30 calls)
Per‑call pricing	$6.75–$9.75 / call (overage ≈ $8–$11)
Key features	24/7 answering, payment collection, call summaries, CRM integrations, spam blocking

“Converts callers into clients. Smith.ai is our inbound sales team. Having a trained and personable voice has transformed our ability to answer the phone and convert callers to clients.” - Jeremy Treister, Owner, CMIT Solutions of Downtown Chicago

For Chicago firms building a defensible AI roadmap, a modern document management platform is the foothold: iManage's cloud‑native knowledge work platform centralizes documents, email, and firm precedents while embedding AI for search, classification, and secure collaboration - capabilities iManage argues are the “bedrock” that must precede advanced generative tools (see iManage's April 23, 2025 research release showing 1,200+ legal professionals prioritize foundational DMS) iManage research: ground your legal AI strategy.

The practical payoff for Illinois practices is concrete: a single, auditable repository reduces citation risk, speeds drafting by surfacing firm‑approved clauses, and preserves chain‑of‑custody needed for malpractice defense - while iManage's security and governance guidance helps meet state and federal data obligations in client matters iManage knowledge work platform overview and iManage guidance on best practices for securing law firm data in the era of AI.

Complementary vendors (Litera, vLex, Ghostwriter Legal) compete in the same knowledge‑and‑drafting layer, but Chicago teams should start by shoring up DMS adoption and human‑in‑the‑loop policies so AI pilots deliver measurable, auditable time savings rather than operational risk.

Metric	iManage (reported)
Users	1 million+ worldwide
Fortune 100 reach	42%
AmLaw 200 reach	81%

“As law firms evaluate the potential of AI capabilities, it is equally critical for legal leaders to assess their foundational technology stack, with a keen eye on usage.” - Joy Ganvik, quoted in iManage research release

Choose tools with a checklist that starts with security and ends with a short pilot: require multifactor authentication (MFA), single‑sign‑on (SSO), and encryption in transit and at rest; insist on role‑based access, end‑to‑end activity logging, and downloadable audit trails so your Chicago firm can defend decisions in discovery; vet vendors for SOC 2 or similar audits, clear data‑residency/retention policies, and routine security testing; require human‑in‑the‑loop workflows and validation samples for any generative AI output, and demand a tested incident‑response plan and ongoing staff training before rollout (start with Attorney at Work's security checklist and Clio's 2025 data‑security guide for concrete controls and questions to ask).

Pilot on one matter, measure time saved and citation accuracy, and only scale when audits and human review pass - small pilots pay: recovering one hour per day across three staffers converts to roughly $1,800/month in billable capacity (Smith.ai examples), a measurable “so what” that turns abstract risk management into immediate revenue opportunity.

Finally, prioritize vendors that publish clear onboarding, APIs/integrations with your DMS, and straightforward offboarding/export terms to avoid lock‑in.

Metric	Value (Tabush 2025)
Firms citing cybersecurity as top IT priority	37%
Firms using AI	80%
Firms citing productivity/efficiency as main IT driver	66%

“37% of firms say cybersecurity is their top IT priority.”

Chicago firms should treat 2025 as the year to pilot - not plunge - into legal AI: start with a tight, single‑matter pilot that uses human‑in‑the‑loop review, measures citation accuracy and time saved, and documents results for firm policy before scaling; Illinois is actively moving on disclosure and impact‑assessment rules (so pilots should test compliance workflows against state proposals) - see the NCSL 2025 AI legislation summary for Illinois NCSL 2025 AI Legislation Summary for Illinois.

Require a formal written AI policy (approval workflows, approved apps, supervisor review) as recommended by ISBA practice guidance ISBA guidance: AI in the Small Law Firm - need for a formal written policy, invest in short practical training (for example, Nucamp's 15‑week AI Essentials for Work bootcamp) to make verification repeatable Nucamp AI Essentials for Work bootcamp syllabus, and treat the first month as an audit: if reclaiming one hour per day across three staffers returns roughly $1,800/month, you've turned governance into immediate capacity - then scale with documented prompts, audit logs, and role‑based controls that keep clients and courts protected.

Bill	Title / Focus	Status (per NCSL)
H 3529	AI Governance Principles and Disclosure Act - business disclosures, civil penalties	Pending
S 1366	State Government AI Act - rules for state agency development/procurement, impact assessments	Pending
S 2203	Preventing Algorithmic Discrimination Act - deployer impact assessments and notifications	Pending

“Firms that delay adoption risk falling behind and will be undercut by firms streamlining operations with AI.” - Niki Black