AI Startup Jobs in Chicago
There are currently 347 AI startup jobs in Chicago from 78 companies. Top hiring companies include Databricks, Flexport, Coinflow Labs. FinTech roles make up the largest share of open positions.
78 of the 78 companies hiring in Chicago (100%) have verified funding data — most commonly Series B (17), Series C (15), Series A (9). Source: Fast AI Jobs company dataset, November 2026.
Top Hiring Companies
Databricks
Unified analytics platform for data and AI, helping companies process and analyze big data in the cloud.
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.
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.
Harvey
AI platform for legal professionals, automating legal research, drafting, and analysis tasks.
Fever
Fever is a live-entertainment discovery and ticketing platform (owner of DICE) that helps users find and book concerts, festivals, immersive experiences, and other local events. It operates in 55+ countries and reached unicorn status in 2022.
Ripple
Ripple provides enterprise-grade crypto payments, custody, and stablecoin infrastructure, enabling banks and financial institutions to move money globally using blockchain technology. Based in San Francisco, it is one of the most valuable private crypto companies with a $40B valuation.
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.
AlphaSense
Market intelligence platform using AI to analyze business documents and extract insights for investment professionals.
Recent Job Listings
FAQ
How many AI startup jobs are available in Chicago?
There are currently 347 AI startup jobs in Chicago from 78 companies on Fast AI Startup Jobs.
How many of the companies hiring in Chicago are funded?
78 of the 78 companies hiring in Chicago (100%) have verified funding data, most commonly Series B (17 companies), Series C (15 companies), Series A (9 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 Databricks, Flexport, Coinflow Labs. Visit each company profile for detailed job listings and company information.
What types of roles are most common in Chicago?
FinTech 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.