Top Artificial Intelligence Startups in Chicago, IL

FleetWorks automates the 2B phone calls and emails that the freight industry makes every year. We use voice synthesis, generative AI, and integrations with logistics systems to solve the largest cost in this industry - people. We are a fast-growing startup in the logistics space led by a founding team from companies like Airbnb and Uber Freight. We are a YC backed company. For more information about us, visit ycombinator.com/companies/fleetworks

Augment’s mission is to build AI teammates that empower people to do their best work. We believe AI should amplify, not replace, human intelligence—removing friction, surfacing what matters, and helping teams stay focused on what counts. Our mission is embedded in how we build, scale, and support both our product and our people. When we eliminate busywork and enhance clarity, we unlock more time, more creativity, and more impact. That’s the future of work—and we’re building it today. Augment is the AI teammate platform that helps teams do their best work—faster, smarter, and with greater focus. By integrating directly into existing tools and workflows, Augment automates repetitive tasks, accelerates decision-making, and frees up time for strategic work. Today, teams across industries like logistics, customer operations, and sales use Augment to scale impact and unlock human potential. We’re a venture-backed startup driven by a culture of ownership, velocity, and curiosity. Our team is composed of builders, operators, and technologists who care deeply about solving real-world problems with practical AI. We’re growing fast—and always looking for thoughtful, mission-aligned people to join us.

Autopilot is building the platform enterprises use to deploy, manage, and scale autonomous systems in the physical world. We are still in stealth, but we’ve closed our latest round and are adding key hires to round out our world-class team. From drones to autonomous vehicles, our founding team has built and sold more robots than most teams in the world. Our mission is to free people from repetitive, dangerous, and physically demanding work so they can spend more time doing the things people do best: creating, connecting, solving problems, and caring for one another. We believe the future of work should be more human, not less. Today, bringing robots and other intelligent machines into real business environments remains fragmented, complex, and difficult to scale. Autopilot connects hardware, software, workflows, and human support to turn autonomous technology into reliable operational outcomes. We are currently operating in stealth and working alongside leading enterprises, robotics companies, and infrastructure partners across mission-critical industries. Our team brings experience commercializing autonomous systems, enterprise software, and emerging technologies. We are backed by leading venture and industrial investors. Our philosophy is simple: do good, have fun, and make money. We want to build a consequential company, create meaningful value for our customers and communities, and enjoy the people and the process along the way. If you want to help shape how intelligence enters the physical world while building a future that gives people more freedom, agency, and time for the things that matter, we would love to meet you.

Frontier is on a mission to make hundreds of millions of critical frontline workers superhuman through a hardware and software AI voice wearable. The company, which is headquartered in Chicago and in stealth mode, has multimillion dollar contracts with the U.S. Department of Defense and just raised $5.3M in funding from tier 1 investors, including the first investor in Oculus. The company has more than 10 of the most critical U.S. companies as paid pilot customers, including one of the top 3 largest U.S. steel companies and top five U.S. airlines. It has an extremely talented and ambitious team committed to building a foundational company.

DeepSigns is revolutionizing document processing in the construction industry through advanced AI. We're currently in stealth working with a design partner in solving a critical industry pain point: the time-consuming, error-prone process of extracting meaningful data from contracts, bonds, and financial statements. Our AI-powered platform offers: - Intelligent document processing: Converting complex construction documents into structured, actionable data - Automated data extraction: Transforming unstructured documents into organized, searchable information - Smart document analysis: Quickly processing and standardizing varied document types across construction workflows Initial results: - 95% reduction in document processing time - Potential for millions in cost savings for construction firms - An estimated 1.5 million labor hours saved if our technology was applied across our design partner's industry We're creating a new standard for document processing in construction, moving outside of our current design partner's niche sector to the entire construction ecosystem. Our market is massive and underserved. The U.S. construction industry alone is worth over $1.3 trillion, with billions spent annually on document processing and management. We're well positioned to go after this market. DeepSigns isn't just another AI-wrapper startup. We're tackling real-world problems with solutions that can reshape an entire industry, and our solutions only get better with better frontier models. No worries of being 'steamrolled' here as the models improve. Our goal: become the obvious choice for construction document processing, saving clients time, money, and headaches. Join us in bringing clarity to construction's complex documentation.

Thresh Consulting is a modern digital consulting firm built for the AI era—where strategy, execution, and craft come together to deliver real outcomes with speed. Our specialty is helping organizations design, build, and scale digital products that create exceptional customer experiences and drive value.

Welocalize is a company that provides services to transform content into multiple languages. We have a network of over 250,000 linguistic resources and operate in North America, Europe, and Asia. We offer high-quality training data solutions for machine learning by combining technology and human intelligence to collect, annotate, and evaluate all types of content.

FairwAI is building real-time accountability infrastructure to detect bias in the moments that matter most. We’re solving one of the toughest challenges in tech: how to make fairness not just a principle but a system. From healthcare and hiring to hospitality and housing, bias shows up when people are most vulnerable. FairwAI turns those moments into measurable, actionable data—using AI, computer vision, and behavioral science to flag risks and enable institutional change before harm happens. We’re not a DEI tool. We’re compliance infrastructure for a new era—where safety, dignity, and fairness are non-negotiable. Our team includes engineers, policy thinkers, civil rights advocates, and public interest technologists from MIT, Harvard, Stanford, The UN, and beyond. We’re launching high-impact projects and building the backbone of ethical AI adoption across sectors. For interns & fellows, this is not a coffee-run experience. You’ll co-design tools, analyze live scenarios, and help shape the future of bias detection and remediation. Your work will be mentored, respected, and turned into real-world impact. If you care about fairness, ethics, and building tools that actually change lives—FairwAI is where your skills meet purpose. Join us. Let’s build the infrastructure fairness deserves.