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Andrew May, Insurance Attorney in Chicago, Illinois

Chicago, IL

Trusted insurance attorney serving Chicago.

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Quick answer

Andrew May 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 Andrew May: Andrew May is an attorney based in Chicago, ILLINOIS. The practice focuses on Insurance.

Areas of practice

Practice areas handled by Andrew May

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

Insurance cases in Chicago, Illinois

Andrew 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 Andrew agrees to represent you.

Biography

About Andrew May — Attorney of Illinois insurance experience

Andrew May is an attorney based in Chicago, ILLINOIS. The practice focuses on Insurance.

Andrew is a trial and appellate lawyer in the firm’s Litigation and Insurance Policyholder Practice Groups. Andrew has earned a reputation as a shrewd and versatile litigator capable of tackling the most vexing legal problems.

Andrew has an active commercial litigation practice spanning multiple industries with experience successfully prosecuting and defending a wide variety of litigation and arbitration matters from inception through trial and appeals. Andrew’s dynamic skill set and subject-matter expertise have afforded him a rare fluency in many areas of the law, including breach of contract claims, business torts, fraud, class action defense, partnership and shareholder disputes, defamation, False Claims Act cases, and high-exposure products and personal injury suits. In recognition of his achievements, the Chicago Daily Law Bulletin named Andrew one of the top “40 Under 40 Attorneys to Watch” in 2020.

In addition, Andrew has extensive experience counseling and representing corporate policyholders in a wide range of insurance coverage disputes. Andrew is listed in the 2026 edition of The Best Lawyers in America® for his expertise in Insurance Law and has obtained significant recoveries from insurers in litigation matters across the country. Andrew is also a frequent author and speaker on insurance coverage topics, including serving as the co-author of the Illinois Institute for Continuing Legal Education’s insurance treatise on the “Duty to Defend.”

The clients Andrew represents range from publicly traded companies to startups. Regardless of the type of case or the type of client, Andrew stands ready to develop creative and aggressive strategies to achieve the best possible outcome – whether through prevailing on the merits or settling on favorable terms.

Andrew believes strongly in the importance of doing pro bono work and giving back to the community. In 2021, Andrew received the U.S. District Court for the Northern District of Illinois’s Excellence in Pro Bono Service Award. In 2020, Andrew was honored as an “access to justice champion” by Justice Mary K. Rochford, Chair of the Illinois Supreme Court Commission on Access to Justice.

Andrew's approach to insurance cases

Andrew is a trial and appellate lawyer in the firm’s Litigation and Insurance Policyholder Practice Groups. Andrew has earned a reputation as a shrewd and versatile litigator capable of tackling the most vexing legal problems. Andrew has an active commercial litigation practice spanning multiple industries with experience successfully prosecuting and defending a wide variety of litigation and…

Clients Andrew works with

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

Credentials

Andrew May's legal education and bar admissions

  • Northwestern University

    J.D. · 2009

  • Colgate University

    B.A. · 2005

Jurisdictions

Andrew's state bar admissions

  • Illinois, Illinois S

    ACTIVE

Andrew studied at J.D. in Northwestern University and B.A. in Colgate University.

Law school and academic background

Andrew completed J.D. in Northwestern University and B.A. in Colgate University. Formal legal training is one signal of substantive knowledge — the day-to-day practice Andrew runs in Illinois is where that training gets applied to real client questions.

Recognition

Awards, publications, and recognition of Andrew May

Andrew 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

Andrew May's office in Chicago

Andrew's primary office is at 225 W. Randolph St., Suite 2800, Chicago, Illinois, 60606-1976. In-person meetings are by appointment; a phone intake usually comes first.

Main office

225 W. Randolph St., Suite 2800

Chicago, Illinois 60606-1976

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Client feedback

Client reviews of Andrew May

Andrew 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 Andrew May — what to expect in your first consultation

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

Consultation formats and pricing

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

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

Payment methods and payment plans

Andrew'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 Andrew May

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

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

  • Does Andrew offer a free consultation?

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

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

    Andrew 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 — Andrew 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 Andrew?

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

  • Is Andrew accepting new insurance clients right now?

    Andrew'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

Andrew 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 Andrew'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.