✍🏽 Welcome to Landon’s Loop: your weekly read on Chicago startups!
In this week’s edition #138:
- Could Waymo be coming to Chicago soon
- My upcoming interview with Coinflow CTO at AI Builders Day
- 6 events in Chicago this week
Waymo Makes Moves in Chicago

Waymo has been expanding across the country and the signs are starting to point towards Chicago.
The company recently posted two new Chicago based roles: Operations Enablement Manager and Community and Public Affairs Specialist.
These roles only show up in markets where Waymo is preparing deeper operations, partnerships or early groundwork for deployment.
In addition, Waymo has been advertising in Illinois for a few months.
Waymo is already active in Detroit and Pittsburgh and its national map shows growing clusters in the center of the country.



Chicago is the logical next step.
We’re the third largest city in the US and we’re also one of the largest transportation hubs, with a regional economy built around logistics and mobility. Any autonomous vehicle company that wants national scale has to be here.
The real question is what Chicago needs in order for full Waymo level deployment to happen.
It comes down to three areas.
Policy Alignment
Chicago needs a clear operating pathway for autonomous vehicles on public streets especially around winter safety, data reporting, and defined pilot zones.
Chicago will need a specific framework that mirrors what Phoenix and SF built years ago.
Local lawmakers will also need to be aligned on insurance and first responder training.
Infrastructure readiness
Autonomous fleets need staging sites, maintenance hubs, mapping support, and real time connectivity.
Chicago has the industrial space and its telecom backbone is strong, but zoning and neighborhood approvals will matter.
Waymo sets up in areas with access to major roads, quick testing loops, and strong grid reliability.
Community partnerships
Waymo hires community and public affairs roles only when it is preparing to build long term trust.
Chicago will need tight collaboration across neighborhood groups, business districts, and city agencies that oversee transportation and mobility.
Good local partnerships will accelerate adoption.
The Timeline
Waymo has entered cities after demonstrating value in safety, cost, and reliability. Chicago can benefit on all three fronts.
A safer night time mobility option, support for late shift workers, and new logistics routes all matter for a city built on transportation.

Progress in 2026 is realistic if the new roles signal early groundwork.
Chicago has the scale, density, and transportation heritage to become a flagship autonomous vehicle city.
The next step is alignment between local government, community partners, and private sector operators.
If that happens, Chicago can become a national leader in autonomous vehicle deployment rather than a late adopter watching other cities move first.
AI Builder Day Chicago is Tomorrow
AI Builders Day Chicago is tomorrow!
Join us at the Chicago Intercom HQ for a day full of fireside chats, networking, and working sessions:

I’ll be starting the day with an exclusive fireside featuring Ben Meeder who is the Co-founder and CTO of Coinflow.

Coinflow is transforming the payments space and it is a company I’m genuinely excited about. They connect traditional payment rails with stablecoin technology to enable instant global settlement for trusted, cross border commerce.
A few months ago they announced a Series A.
We’ll talk about everything from scaling an engineering org to why they are bullish on Chicago.
Smarter CX insights for investors and founders
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📆 This Week’s Tech Events
AI Meetup (December): Gen AI, LLMs and Agents
Monday
AI Builders Day
Tuesday
Hosted by Drive Capital, Intercom, Hyde Park Venture Partners, and M25
AI Tinkerers December Meetup (2025 Finale)
Tuesday
Hosted by Drive Capital
1 Million Cups
Wednesday
MCP Tools: Defending Autonomous Agents
Thursday
Building in Chi: Coffee + Cowork
Thursday


