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Maddie San Jose, Insurance Attorney in Chicago, Illinois

Chicago, IL

Trusted insurance attorney serving Chicago.

Practices in

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Quick answer

Maddie San Jose is an attorney based in Chicago, ILLINOIS. The practice focuses on Insurance.

Based in
Chicago, ILLINOIS
Experience
attorney
Known for
Insurance
  • Handles Insurance matters from Chicago, ILLINOIS.
  • Recognized with Best Lawyers in America — Insurance Law (2026).

About Maddie San Jose: Maddie San Jose is an attorney based in Chicago, ILLINOIS. The practice focuses on Insurance.

Areas of practice

Legal matters Maddie takes on

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

Insurance cases in Chicago, Illinois

Maddie 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 Maddie agrees to represent you.

Biography

Meet Maddie San Jose — insurance lawyer in Chicago

Maddie San Jose is an attorney based in Chicago, ILLINOIS. The practice focuses on Insurance.

Maddie San Jose is a top attorney recognized by Best Lawyers in the practice area(s) of Insurance Law.

Maddie, who practices law in Chicago, Illinois, has been recognized since 2026. This recognition is based on an exhaustive peer-review survey, reflecting the high esteem in which Maddie is held by other top lawyers in the same geographic and legal practice area.

How Maddie handles insurance matters

Maddie San Jose is a top attorney recognized by Best Lawyers in the practice area(s) of Insurance Law. Maddie, who practices law in Chicago, Illinois, has been recognized since 2026. This recognition is based on an exhaustive peer-review survey, reflecting the high esteem in which Maddie is held by other top lawyers in the same geographic and legal practice area.

The kind of cases Maddie takes

Maddie reviews new inquiries case-by-case for insurance matters in Chicago and the surrounding Illinois area.

Credentials

Education, bar admissions, and languages

  • Indiana University Maurer School of Law

    J.D. · 2022

Maddie studied at J.D. in Indiana University Maurer School of Law.

Law school and academic background

Maddie completed J.D. in Indiana University Maurer School of Law. Formal legal training is one signal of substantive knowledge — the day-to-day practice Maddie runs in Illinois is where that training gets applied to real client questions.

Recognition

Recognition and thought leadership

Maddie has received 1 formal recognition from bar associations, industry bodies, and peer-review services.

  • Best Lawyers in America — Insurance Law

    2026

Legal awards and honors

Best Lawyers in America — Insurance Law (2026).

Locations

Maddie San Jose's office in Chicago

Maddie's primary office is at 444 West Lake Street, Chicago, Illinois, 60606-0029. In-person meetings are by appointment; a phone intake usually comes first.

Main office

444 West Lake Street

Chicago, Illinois 60606-0029

Open in Google Maps

Client feedback

Client reviews of Maddie San Jose

Maddie 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 Maddie San Jose — what to expect in your first consultation

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

Consultation formats and pricing

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

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

Payment methods and payment plans

Maddie'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 Maddie San Jose

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

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

  • Does Maddie offer a free consultation?

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

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

    Maddie 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 — Maddie 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 Maddie?

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

  • Is Maddie accepting new insurance clients right now?

    Maddie'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

Maddie 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 Maddie'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.