Chicago vs. San Francisco: A Tale of Two Tech Markets

The Great Divide

When we analyze the flow of job requisitions on JobsJudo, distinct patterns emerge geographically. While remote work has flattened the world, local job markets still retain unique DNA. Today, we're putting two heavyweights head-to-head: San Francisco, the undisputed global capital of tech, and Chicago, the resilient powerhouse of the Midwest.

The data reveals two very different stories. One is a market hyper-focused on the next frontier of Artificial Intelligence. The other is a diversified ecosystem supporting the backbone of American industry.

1. Volume: The Scale Gap

First, let's address the elephant in the room: volume. Despite reports of an exodus, San Francisco remains a behemoth. Our active job sensors detect approximately 5.9x more active technology roles in San Francisco compared to Chicago.

• San Francisco: ~3,700 active visible roles
• Chicago: ~630 active visible roles

This sheer density means that for every one opportunity in the Windy City, there are nearly six by the Bay. However, volume isn't everything. Competition in SF is famously fierce, potentially offsetting the abundance of roles.

2. The AI Obsession vs. Practical SaaS

The most striking difference lies in what companies are hiring for. San Francisco has gone all-in on AI.

In San Francisco, nearly one in three new posted jobs is explicitly tagged or categorized within AI & Machine Learning. It's a gold rush.

Chicago, by contrast, is diversified. Its top sector, B2B SaaS, comprises only 17% of the market. Significant portions of the market are dedicated to Healthcare, Cybersecurity, and even Construction technology. Chicago builds the software that runs real-world businesses.

3. The Seniority Squeeze

Both markets show a strong preference for experienced talent, a trend we've observed globally. However, San Francisco leans slightly more senior.

In both cities, the ratio of Senior roles to Junior roles is steep.

• Chicago Ratio: ~1.8 Senior roles for every 1 Junior role.
• San Francisco Ratio: ~2.6 Senior roles for every 1 Junior role.

This suggests that while breaking in is hard everywhere, SF's market is particularly "top-heavy," likely driven by the need for specialized, high-level AI expertise that junior engineers simply haven't had time to develop yet.

Conclusion

If you are an engineer specializing in LLMs, Agents, or ML infrastructure, San Francisco is undeniably the place to be—physically or digitally. The concentration of opportunity there is unmatched.

However, for those seeking roles in established industries like Healthcare or Logistics, or looking for a market that isn't entirely dependent on the AI hype cycle, Chicago offers a surprisingly robust and grounded alternative.