AI Startup Jobs in Chicago
There are currently 241 AI startup jobs in Chicago from 56 companies. Top hiring companies include Flexport, Databricks, Harvey. Logistics & Supply Chain roles make up the largest share of open positions.
56 of the 56 companies hiring in Chicago (100%) have verified funding data — most commonly Series B (17), Series C (13), Series A (7). Source: Fast AI Jobs company dataset, September 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.
Databricks
Unified analytics platform for data and AI, helping companies process and analyze big data in the cloud.
Harvey
AI platform for legal professionals, automating legal research, drafting, and analysis tasks.
Coinflow Labs
Coinflow is a payment service provider that lets merchants, web3 games, and consumer apps accept traditional card payments and settle instantly using stablecoins. Its API handles global card acceptance across 170+ countries, fraud prevention, merchant underwriting, and crypto-to-USD payouts to bank accounts. Founded in 2022 and headquartered in Chicago, it raised a $25M Series A led by Pantera Capital in October 2025.
AlphaSense
Market intelligence platform using AI to analyze business documents and extract insights for investment professionals.
Legora
Collaborative AI workspace for lawyers to research, draft, and review faster.
Engine
Engine is a modern business travel platform that helps companies book, manage, and optimize work travel at scale.
Loop
Loop is a San Francisco-based, full-stack AI platform for logistics and supply chains that ingests and normalizes fragmented shipment, carrier, and financial data to give shippers visibility and predict and prevent disruptions. Its DUX family of logistics-specific models and agents automates freight audit, payment, and accounts payable/receivable decisions. Customers include Olipop, Kendra Scott, and Dot Foods.
Recent Job Listings
FAQ
How many AI startup jobs are available in Chicago?
There are currently 241 AI startup jobs in Chicago from 56 companies on Fast AI Startup Jobs.
How many of the companies hiring in Chicago are funded?
56 of the 56 companies hiring in Chicago (100%) have verified funding data, most commonly Series B (17 companies), Series C (13 companies), Series A (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, Databricks, Harvey. Visit each company profile for detailed job listings and company information.
What types of roles are most common in Chicago?
Logistics & Supply Chain 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.