AI Startup Jobs in Chicago
There are currently 242 AI startup jobs in Chicago from 53 companies. Top hiring companies include Flexport, Harvey, Databricks. Legal Tech roles make up the largest share of open positions.
53 of the 53 companies hiring in Chicago (100%) have verified funding data — most commonly Series B (15), Series C (8), Series D (7). Source: Fast AI Jobs company dataset, August 2026.
Top Hiring Companies
Flexport
Flexport is a technology-enabled freight forwarding and supply chain logistics platform that combines software, data, and operational services to help businesses manage global trade and freight movement. The company offers ocean and air freight, customs brokerage, trucking coordination, and fulfillment solutions for over 13,000 companies across more than 147 countries.
Harvey
AI platform for legal professionals, automating legal research, drafting, and analysis tasks.
Databricks
Unified analytics platform for data and AI, helping companies process and analyze big data in the cloud.
Engine
Engine is a modern business travel platform that helps companies book, manage, and optimize work travel at scale.
AlphaSense
Market intelligence platform using AI to analyze business documents and extract insights for investment professionals.
Filevine
Filevine is a legal operating platform that integrates AI for case management, document assembly, lead management, and billing for law firms. The platform serves nearly 6,000 customers and 100,000 legal professionals. Founded in 2014 in Salt Lake City, Filevine reached unicorn status at a $3B valuation following its $400M Series E in 2025.
Ashby
Ashby is an all-in-one recruiting platform that combines an applicant tracking system, CRM, scheduling automation, and analytics into a single product. Used by companies like OpenAI, Notion, and Ramp, it helps ambitious hiring teams scale with AI-powered workflows and deep recruiting insights.
Writer
WRITER provides a full-stack enterprise generative AI platform for building, activating, and supervising AI agents and workflows grounded in company data, with enterprise-grade LLMs, governance, and deployment tools.
Recent Job Listings
FAQ
How many AI startup jobs are available in Chicago?
There are currently 242 AI startup jobs in Chicago from 53 companies on Fast AI Startup Jobs.
How many of the companies hiring in Chicago are funded?
53 of the 53 companies hiring in Chicago (100%) have verified funding data, most commonly Series B (15 companies), Series C (8 companies), Series D (7 companies). Funding stage and amount are tracked for roughly 97% of all companies in the Fast AI Jobs dataset.
Which companies are hiring the most in Chicago?
The top hiring companies in Chicago include Flexport, Harvey, Databricks. Visit each company profile for detailed job listings and company information.
What types of roles are most common in Chicago?
Legal Tech roles make up the largest share of AI startup jobs in Chicago. Other common categories include engineering, research, product, and operations roles.
How often are these job listings updated?
Job listings are refreshed daily from official company career pages and public job boards. All links point directly to original application pages.
Where do the job links go?
Job links point to official company career pages or public job listings, not re-hosted application forms.