Gregory S. Bailey, Insurance Attorney in Chicago, Illinois

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

• Insurance

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• Litigation

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• Personal Injury

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Gregory's primary office is at 155 N. Wacker Drive, Chicago, IL, 60606. In-person meetings are by appointment; a phone intake usually comes first.

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

Gregory 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.

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

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

• Does Gregory offer a free consultation?

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

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

  Gregory 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 — Gregory 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 Gregory?

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

• Is Gregory accepting new insurance clients right now?

  Gregory's intake status shifts week to week. Submit the form; the office will confirm availability or refer the matter out.