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Cheryl A. Fleming, Insurance Attorney in Chicago, Illinois

Over 45 years of legal practice · focused on Insurance, Litigation, and Personal Injury

PartneratParrillo, Weiss & O'Halloran

Chicago, IL

Practicing insurance in Chicago since 1981.

45+
Years practicing
2
Bar admissions

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Quick answer

Cheryl A. Fleming is a partner based in Chicago, IL. The practice focuses on Insurance, Litigation, and Personal Injury. Cheryl has over 45 years of legal experience. Currently practicing at Parrillo, Weiss & O'Halloran.

Based in
Chicago, IL
Experience
over 45 years
Known for
Insurance · Litigation · Personal Injury
  • Handles Insurance, Litigation, and Personal Injury matters from Chicago, IL.
  • Over 45 years of practice as a licensed attorney.

About Cheryl A. Fleming: Cheryl A. Fleming is a partner based in Chicago, IL. The practice focuses on Insurance, Litigation, and Personal Injury. Cheryl has over 45 years of legal experience. Currently practicing at Parrillo, Weiss & O'Halloran.

Areas of practice

Practice areas handled by Cheryl A. Fleming

Cheryl concentrates on insurance, litigation, and personal injury. Each area below outlines the kind of case Cheryl handles, typical outcomes to expect, and how the intake process starts.

Insurance cases in Chicago, Illinois

Cheryl 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 Cheryl agrees to represent you.

Litigation cases in Chicago, Illinois

Cheryl takes litigation 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 Cheryl agrees to represent you.

Personal Injury cases in Chicago, Illinois

Cheryl takes personal injury 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 Cheryl agrees to represent you.

Biography

About Cheryl A. Fleming — Over 45 years of Illinois insurance experience

Cheryl A. Fleming is a partner based in Chicago, IL. The practice focuses on Insurance, Litigation, and Personal Injury. Cheryl has over 45 years of legal experience. Currently practicing at Parrillo, Weiss & O'Halloran.

Cheryl A. Fleming is a lawyer practicing insurance, personal injury, litigation. Cheryl received a B.S.N. degree from Northern Illinois University in 1976, and has been licensed for 45 years. Cheryl practices at Parrillo, Weiss & O'Halloran in Chicago, IL.

How Cheryl handles insurance matters

Cheryl A. Fleming is a lawyer practicing insurance, personal injury, litigation. Cheryl received a B.S.N. degree from Northern Illinois University in 1976, and has been licensed for 45 years. Cheryl practices at Parrillo, Weiss & O'Halloran in Chicago, IL.

Who Cheryl represents

Cheryl reviews new inquiries case-by-case for insurance, litigation, and personal injury matters in Chicago and the surrounding Illinois area.

Credentials

Cheryl A. Fleming's legal education and bar admissions

  • Loyola University School of Law

    J.D. · 1981

  • Northern Illinois University

    B.S.N. · 1976

Jurisdictions

Cheryl's state bar admissions

  • Illinois

    1981 · ACTIVE

  • U.S. District Court,

    1981 · ACTIVE

Cheryl studied at J.D. in Loyola University School of Law and B.S.N. in Northern Illinois University.

Law school and academic background

Cheryl completed J.D. in Loyola University School of Law and B.S.N. in Northern Illinois University. Formal legal training is one signal of substantive knowledge — the day-to-day practice Cheryl runs in Illinois is where that training gets applied to real client questions.

Locations

Cheryl A. Fleming's office in Chicago

Cheryl's primary office is at 77 W. Wacker Dr., 50th Fl., Chicago, IL, 60601. In-person meetings are by appointment; a phone intake usually comes first.

Main office

Parrillo, Weiss & O'Halloran

77 W. Wacker Dr., 50th Fl.

Chicago, IL 60601

Open in Google Maps

Client feedback

Client reviews of Cheryl A. Fleming

Cheryl has not yet collected verified client reviews on LawyersListed. Reviews here are all from confirmed clients; anonymous ratings are moderated out.

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Hiring guide

How to hire Cheryl A. Fleming — what to expect in your first consultation

Working with a new insurance attorney should feel structured. Here's how the first two conversations with Cheryl usually go, from the moment you request a consult to the day representation begins.

Consultation formats and pricing

Cheryl charges for the initial consult. That fee is credited toward representation if you retain Cheryl'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; Cheryl 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 Cheryl

Cheryl 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. Cheryl confirms the model in the engagement letter before any work starts.

Payment methods and payment plans

Cheryl'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 Cheryl A. Fleming

  • How much does it cost to hire Cheryl for a insurance case?

    Cost depends on the type of matter, the fee model (contingency, flat, hourly), and how contested the case becomes. Cheryl walks through the likely range during the consult so there are no surprises.

  • Does Cheryl offer a free consultation?

    Cheryl charges for the initial consult; that fee is credited toward representation if you retain Cheryl's office. Some insurance attorneys offer free consults — check Cheryl'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. Cheryl gives a realistic estimate for your facts at the consult — vague answers here are a red flag.

  • Can Cheryl take my case if I'm outside Chicago?

    Cheryl 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 — Cheryl 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 Cheryl?

    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. Cheryl will filter what matters — over-preparing at intake is always cheaper than needing a second meeting.

  • Is Cheryl accepting new insurance clients right now?

    Cheryl'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

Cheryl 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

If Cheryl'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.