By Cary Shepherd on 2026-10-01
Shepherd Law today announced its Chicago parking ticket app, an AI-powered, attorney-backed service that lets drivers contest City of Chicago tickets in a few minutes from their phone.
"Most people pay tickets they could have beaten, because fighting one takes time and nobody hires a lawyer over a parking ticket," said founder Cary Shepherd. "We built a way to give every driver real legal representation for the price of a lunch."
How It Works
- Snap a photo. Take a picture of your ticket. The app reads the ticket number, violation, date, and location for you, and handles several tickets at once.
- Tell us what happened. Type, tap a reason, or just talk. The app asks one question at a time, like a text conversation.
- Get an honest answer. The AI checks your story against the grounds the City of Chicago accepts for dismissing a ticket, tells you how strong your case is, and tells you exactly what proof would help, such as a photo of the sign or your parking receipt.
- A lawyer files it. You get a clear, formal statement with your evidence attached. A Shepherd Law attorney reviews it and submits it to the City for you.
Simple, Fair Pricing
- Strong cases are no win, no fee. Pay nothing today. You pay $10 only if the City does not reject your contest.
- Everything else is a flat $10 per ticket, paid when you submit.
Checkout is handled securely by Stripe, and you can pay by card, Apple Pay, or Google Pay. You can track every contest in your client portal.
What's Covered
The app handles City of Chicago parking, compliance, red light camera, and speed camera tickets. Contests are filed through the City's contest-by-mail process, so there is no need to go to a hearing in person.
Part of a Bigger Mission
The app reflects Shepherd Law's mission: using AI to make real legal help affordable for everyday people. AI does the reading, organizing, and drafting; licensed Illinois attorneys provide the judgment and representation.