James Michael Hilly, Insurance Attorney in Chicago, Illinois
Over 38 years of legal practice · focused on Insurance and Tax
AttorneyatMacCabe & McGuire
Chicago, IL
Practicing insurance in Chicago since 1988.
- 38+
- Years practicing
- 3
- Bar admissions
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Quick answer
James Michael Hilly is an attorney based in Chicago, IL. The practice focuses on Insurance and Tax. James has over 38 years of legal experience. Currently practicing at MacCabe & McGuire.
- Based in
- Chicago, IL
- Experience
- over 38 years
- Known for
- Insurance · Tax
- Handles Insurance and Tax matters from Chicago, IL.
- Over 38 years of practice as a licensed attorney.
About James Michael Hilly: James Michael Hilly is an attorney based in Chicago, IL. The practice focuses on Insurance and Tax. James has over 38 years of legal experience. Currently practicing at MacCabe & McGuire.
Areas of practice
Practice areas handled by James Michael Hilly
James concentrates on insurance and tax. Each area below outlines the kind of case James handles, typical outcomes to expect, and how the intake process starts.
Insurance cases in Chicago, Illinois
James takes insurance matters in Chicago, Illinois. Typical engagements include intake calls to scope the issue, review of any records or filings you already have, and a written strategy memo before James agrees to represent you.
Tax cases in Chicago, Illinois
James takes tax matters in Chicago, Illinois. Typical engagements include intake calls to scope the issue, review of any records or filings you already have, and a written strategy memo before James agrees to represent you.
Biography
About James Michael Hilly — Over 38 years of Illinois insurance experience
James Michael Hilly is an attorney based in Chicago, IL. The practice focuses on Insurance and Tax. James has over 38 years of legal experience. Currently practicing at MacCabe & McGuire.
James Michael Hilly is a lawyer practicing insurance defense, taxation law. James Michael received a B.S. degree from University of Buffalo in 1983, and has been licensed for 38 years. James Michael practices at MacCabe & McGuire in Chicago, IL.
James's approach to insurance cases
James Michael Hilly is a lawyer practicing insurance defense, taxation law. James Michael received a B.S. degree from University of Buffalo in 1983, and has been licensed for 38 years. James Michael practices at MacCabe & McGuire in Chicago, IL.
The kind of cases James takes
James reviews new inquiries case-by-case for insurance and tax matters in Chicago and the surrounding Illinois area.
Credentials
James Michael Hilly's legal education and bar admissions
Boston University
J.D. Taxation · 1987
University of Buffalo
B.S. · 1983
Jurisdictions
James's state bar admissions
U.S. District Court,
1991 · ACTIVE
Illinois
1990 · ACTIVE
Massachusetts
1988 · ACTIVE
James studied at J.D. Taxation in Boston University and B.S. in University of Buffalo.
Law school and academic background
James completed J.D. Taxation in Boston University and B.S. in University of Buffalo. Formal legal training is one signal of substantive knowledge — the day-to-day practice James runs in Illinois is where that training gets applied to real client questions.
Locations
James Michael Hilly's office in Chicago
James's primary office is at Suite 3333, 77 West Wacker Drive, Chicago, IL, 60601. In-person meetings are by appointment; a phone intake usually comes first.
Client feedback
Client reviews of James Michael Hilly
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Schedule your consultationHiring guide
How to hire James Michael Hilly — what to expect in your first consultation
Working with a new insurance attorney should feel structured. Here's how the first two conversations with James usually go, from the moment you request a consult to the day representation begins.
Consultation formats and pricing
James charges for the initial consult. That fee is credited toward representation if you retain James's office.
What to bring to your first meeting
Bring any documents you already have — police reports, medical records, filed pleadings, correspondence from an insurer, a copy of the contract at issue. If you're not sure, err on the side of bringing everything; James will tell you what matters and what doesn't.
Questions to ask a insurance attorney in Chicago, Illinois
A short list to run through before you commit: How many insurance matters have you handled in the last year? What's your fee structure? Who else in the office will work on this? What's your realistic estimate of timeline and range of outcomes? How do I reach you between meetings?
Fees & payment
Fees, payment methods, and consultation options for James
James discusses fees during intake so the arrangement fits the matter. Contingency, hourly, and flat-fee options are all common in insurance practice — ask which fits.
Hourly rates, contingency fees, and flat-fee options
Every insurance matter is priced differently. Simple document review might be a flat fee. Injury litigation is often contingency. Complex commercial disputes usually run hourly with a retainer. James confirms the model in the engagement letter before any work starts.
Payment methods and payment plans
James's office accepts standard payment methods. Ask about payment plans if the retainer is a stretch — many insurance practices work with clients on structured schedules.
Frequently asked
Frequently asked questions about James Michael Hilly
How much does it cost to hire James for a insurance case?
Cost depends on the type of matter, the fee model (contingency, flat, hourly), and how contested the case becomes. James walks through the likely range during the consult so there are no surprises.
Does James offer a free consultation?
James charges for the initial consult; that fee is credited toward representation if you retain James's office. Some insurance attorneys offer free consults — check James's current terms during booking.
How long do insurance cases in Illinois typically take?
Simple insurance matters can wrap in a few weeks; disputed cases can run 6–18 months from intake to resolution, longer if the matter goes to trial. James gives a realistic estimate for your facts at the consult — vague answers here are a red flag.
Can James take my case if I'm outside Chicago?
James is licensed in Illinois. Matters governed by Illinois law are the natural fit. Out-of-state matters are handled case-by-case, sometimes with local co-counsel. Ask during intake — James will tell you if the case is a fit or refer you to someone closer to your court.
What should I bring to my first meeting with James?
Bring every document that touches the dispute: contracts, correspondence, police or medical reports, filed pleadings, invoices, photographs, insurance letters. Also bring a written timeline of what happened, in your own words. James will filter what matters — over-preparing at intake is always cheaper than needing a second meeting.
Is James accepting new insurance clients right now?
James's intake status shifts week to week. Submit the form; the office will confirm availability or refer the matter out.
Areas served
Insurance attorneys serving Chicago, Springfield and Northbrook in Illinois
James handles insurance matters throughout Illinois. Each city below is a direct link into the search page for verified insurance attorneys in that community.
More counsel
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If James's intake is full or the fit isn't right, these insurance attorneys in Chicago handle similar matters. Every profile below is verified and open to consultations.





