🔥 January 20, 2026 from 5:30 PM – 7:30 PM 🔥

Join the Chicago chapter for our first meetup of 2026. This is a curated, high-signal room for active builders to dissect working code, share messy experiments, and accelerate their roadmaps.

Space is highly limited. Attendance is strictly screened to ensure the room is filled only with fellow engineers, founders, and researchers who are actively shipping AI.

The focus remains on practical implementation. We are here to see the systems you built, the trade-offs you made, and the architectural decisions that enabled your project to ship—especially as the frontier advances in reasoning (GPT-5.2, Claude Opus 4.5) and agentic workflows (Claude Code, MCP).

Huge thanks to our friends at PostHog for partnering with us on the first AI Tinkerers Chicago of 2026

PostHog  aims to equip every developer to build successful products by providing the tools teams need to capture events, analyze data, record user sessions, conduct experiments, deploy new features, track errors, run surveys, provision data warehouses, observe LLM-powered features, and more, all in one platform.

Founded in January 2020 by James Hawkins and Tim Glaser, PostHog was a member of Y Combinator’s Winter 2020 batch, and has subsequently raised $182M in funding from Stripe, GV, Y Combinator, and notable angel investors including Jason Warner (CTO, GitHub), Solomon Hykes (Founder, Docker), and others.

You can read more about PostHog’s story, where they’re going, and more about the company culture here. 

Learn about PostHog’s 15+ products or sign up for their startup program

Live Demos: Architecture, Trade-offs, and What Broke

We are accepting proposals for short, technical show-and-tell demos. Skip the slides and product pitches; focus on the implementation details. Your five-minute demo should answer one core question: “How did you build this interesting thing?”

We want to see your latest hacks, novel context engineering setups, complex agentic orchestration, or hard-won lessons from deployment.

Submit Your Demo Proposal:
Submit Your Demo Proposal

Schedule and Logistics

• Date: Tuesday, January 20, 2026
• Time: 5:30 PM – 7:30 PM
• Location: Chicago, IL (Specific venue details will be provided only to accepted attendees.)

Curation Policy

AI Tinkerers is selective by design. We screen every registration to maintain a high-trust room for candid technical work. If you are an active builder—an engineer, founder, or researcher who ships code—we encourage you to register above.

📊 AI Tinkerers Chicago Stats

• Attendees: This exclusive community of 2,189 subscribers comprises 52% AI/ML specialists and 68% full-stack engineers, with 32% holding founder or executive titles. Members represent elite institutions like UChicago, UIUC, and Google. Notable achievements include deploying production-grade agentic workflows, building open-source developer platforms, and engineering FDA-cleared medical AI, making this Chicago’s premier hub for high-signal technical collaboration.
• Companies Represented: Featuring tech giants and AI leaders like Google, Microsoft, NVIDIA, and Waymo, alongside fast-growing platforms such as DoorDash, Robinhood, TikTok, and Pinecone, and emerging startups like ElevenLabs, HumanLayer, Autonoma AI, and pieces.app, and more
• Demos: 184 demos have been submitted and 107 have been presented. The most exciting themes have centered on agentic workflows, retrieval and knowledge-centric systems, and production-grade reliability via evals, observability, and guardrails. Technical exploration has also highlighted structured generation (function calling and schemas), efficiency/cost optimization for LLM pipelines, and practical multimodal/document processing.
• Testimonials:

  “Please continue organizing interactive AI events with industry professionals and real-world discussions about technology trends, career opportunities, and practical AI applications. ... Events like this are very helpful for students and professionals looking to grow their technical skills and better understand the future of AI and technology.”

  — QA engineer, cloud support

  “For the people that don't get to present, what if their work could be featured in some way that allows others to see a demo online or read a deck describing the work (or both)... This is such a great idea. I signed up right away. ... Your network puts you in a unique position to really make this idea scale...”

  — Founder, crypto AI

  “Such a cool concept”

  — Devrel @ web3 foundation

  “Leaders from successful startups as speakers is great. Love hearing from my tinkerers but it was clear alpha in building a business and companies actually hiring created a different vibe.”

  — Founder, GTM strategy

  “Keep up the good work. This group is a really great way to stay connected to what's happening with AI in Chicago.”

  — Founder, crypto AI

  “Please keep organizing highly technical, builder-focused AI events like this in Chicago.”

  — R&D engineer, defense tech

  “I enjoyed the breakout room like discussions from the previous Meetup hosted by Zapier. Those allowed us to easily connect and talk about experiences.”

  — Applied AI engineer