Chicago, IL
AI Engineer jobs in Chicago, IL
3 open roles from 3 employers. Checked Oct 6, 2026.
What these openings look like
3 employers are hiring here: Optiver, Stripe and Chicago Trading Company. None of these postings publish a pay range. The most recent went up on Oct 2, 2026.
Every listing links to the employer's own application. Nothing is posted here on their behalf, and nothing is reposted from anywhere else.
Open roles
What they ask ai engineer candidates here
Drawn from the 3 open postings on this page. The ones that come up across several employers are near the top.
Tell me about a production AI system you built and owned. How did you know it was working?
What they are checking: Whether they have shipped and operated real AI systems, with measured results rather than just demos.
How would you build an evaluation framework for an AI assistant used by engineers?
What they are checking: Whether they can define success metrics and test sets that catch regressions before users do.
How do you choose between foundation models for a task?
What they are checking: Whether they compare models on capability, reliability, latency, security and cost, as the posting describes.
Walk me through how you would design a code review harness that uses an AI model.
What they are checking: Whether they can design an agentic tool that is useful, measurable and trusted by engineers.
A business team asks for an AI tool, but the problem is vague. How do you turn it into something you can build?
What they are checking: Whether they can translate ambiguous problems into clear, scoped AI solutions with real business value.
How do you keep an AI agent safe when it can take actions in internal systems?
What they are checking: Whether they think about permissions, sandboxing and human review before giving agents real power.
Your AI system starts giving worse answers after a model update. How do you figure out what happened?
What they are checking: Whether they rely on observability and evaluations to diagnose quality changes, not just intuition.
How do you handle sensitive or proprietary data when using third-party AI services?
What they are checking: Whether they protect firm data with clear rules about what can be sent where.
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