CADDi, which is headquartered in both Chicago and Tokyo, raised the largest Chicago AI round in this guide for 2026: a $114 million Series D in September at a reported $1.2 billion valuation. Its software reads engineering drawings and production records so manufacturers can find duplicate parts and cut procurement costs. Go.AI, which sells on-premises AI hardware and software to banks and credit unions, raised an $85 million Series A the same month, and restaurant software company Chowbus raised $81 million in March.
Most of the other rounds in this guide were $10 million to $40 million, raised by AI companies serving health care, insurance, manufacturing, trucking and sales teams. Two larger 2025 rounds with Chicago ties, Nerdio‘s $500 million Series C and Pathos AI‘s $365 million Series D, are covered in their own section below.
This guide covers notable rounds raised in 2025 and 2026 by AI companies headquartered in Chicago, the established AI companies in the city, and the investors and institutions behind them.
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Notable Chicago AI rounds of 2025
- CADDi raised a $38 million extension of its Series C in March 2025, led by Atomico, with existing investors Global Brain and Minerva Growth.
- Hoppr, which gives developers medical imaging data and tools to build and train imaging AI models, raised a $31.5 million Series A co-led by Kivu Ventures and Greycroft in June 2025.
- Sibel Health, a Northwestern University spinout that makes wireless wearable sensors with AI analytics to flag when hospital patients are getting worse, raised a $30 million Series C led by the Steele Foundation for Hope in March 2025, with Dräger taking part. In October it extended the round to $39 million, adding Maruho and Samsung Next.
- Empirical Security, which builds machine learning models that predict which software vulnerabilities attackers will exploit, raised a $12 million seed round led by Costanoa Ventures in July 2025.
- Xenia, an app that frontline teams at multi-location businesses use to run tasks, inspections and compliance checks, raised a $12 million Series A from PSG in November 2025.
Two large 2025 rounds with Chicago ties
Nerdio, a Chicago software company, raised a $500 million Series C led by General Atlantic in March 2025, with Lead Edge Capital and StepStone also investing. The round valued the company at more than $1 billion. Nerdio’s main product automates how companies deploy and manage Microsoft Azure Virtual Desktop and Windows 365, and it has added AI features across its products.
Pathos AI raised a $365 million Series D in May 2025 at a valuation of about $1.6 billion. It was founded in Chicago in 2020 by Tempus founder Eric Lefkofsky and Ryan Fukushima, and it now has offices in both Chicago and New York, where it announced the round. Pathos uses AI and patient data to choose cancer drug candidates and the patients most likely to respond to them in trials.
Notable Chicago AI rounds of 2026 so far
CADDi’s September Series D brought its total funding to $234 million. New investors included Moore Strategic Ventures, Coreline Ventures, Woven Capital and Salesforce Ventures, and Atomico and Globis Capital Partners returned. The company is using the money to grow in North America.
Go.AI, formerly called Go Abacus, raised its $85 million Series A from Updata Partners, which led, with GFT Ventures and LAUNCH. Its Go1 hardware and Go.OS software let regulated organizations run AI models on their own premises instead of in a public cloud. Chowbus’s $81 million round was co-led by Prysm Capital and Left Lane Capital. The company sells a point-of-sale and operating system to independent restaurants, with AI tools for marketing and analytics.
Other notable 2026 rounds went to sales software, insurance, security, health care, data infrastructure and logistics:
- Letter AI, which builds AI tools that train and support enterprise sales teams, raised a $40 million Series B led by Battery Ventures in February 2026. Y Combinator, Lightbank and Northwestern Mutual Future Ventures also invested.
- Honeycomb Insurance, which insures apartment buildings and condo associations and prices each property from data instead of a physical inspection, raised $40 million led by Zeev Ventures in June 2026.
- KeyCare, a virtual care company built within the Epic health record system, raised $27.4 million led by HealthX Ventures in March 2026 to expand its AI-enabled care for health systems. University of Chicago Ventures was among the investors.
- Empirical Security followed its seed round with a $25 million Series A led by Brightmind Partners in July 2026, bringing its total to $37 million.
- Prenosis, whose Sepsis ImmunoScore is an FDA-authorized AI tool that estimates a patient’s risk of sepsis, raised a $20 million Series A led by PACE Healthcare Capital in January 2026. It announced a separate $20 million federal contract at the same time, which is not counted here.
- ONTO Health, a physician-led fertility and longevity provider that uses AI diagnostics, raised a $20 million Series A from ARTIS and Humania in April 2026.
- Nara Health, which runs health benefits administration for employers on AI software, raised $14 million across its pre-seed and seed rounds, led by Khosla Ventures, in September 2026.
- definity, which uses AI agents to tune data engineering pipelines, raised a $12 million Series A led by GreatPoint Ventures in April 2026.
- Datatruck, an operating system with built-in AI agents for long-haul trucking carriers, raised a $12 million Series A led by Avenue Growth Partners in January 2026.
- Qumis, whose AI analyzes commercial insurance policies for coverage questions, raised a $4.3 million seed round led by MTech Capital in February 2026, with American Family Ventures joining.
Chicago AI startups at a glance
The table lists the rounds covered above, newest first.
| Company | What it builds | Funding | Date |
|---|---|---|---|
| CADDi | AI for manufacturing drawings and procurement data | $114M Series D, reported $1.2B valuation | Sep 2026 |
| Go.AI | On-premises AI hardware and software | $85M Series A led by Updata Partners | Sep 2026 |
| Nara Health | AI health benefits administration | $14M pre-seed and seed led by Khosla Ventures | Sep 2026 |
| Empirical Security | Vulnerability exploit prediction | $25M Series A led by Brightmind Partners | Jul 2026 |
| Honeycomb Insurance | Data-priced insurance for apartment buildings | $40M led by Zeev Ventures | Jun 2026 |
| ONTO Health | Fertility and longevity care with AI diagnostics | $20M Series A from ARTIS and Humania | Apr 2026 |
| definity | AI agents for data pipelines | $12M Series A led by GreatPoint Ventures | Apr 2026 |
| Chowbus | Restaurant point-of-sale and operating system | $81M co-led by Prysm Capital and Left Lane Capital | Mar 2026 |
| KeyCare | Virtual care for health systems | $27.4M led by HealthX Ventures | Mar 2026 |
| Letter AI | AI sales enablement | $40M Series B led by Battery Ventures | Feb 2026 |
| Qumis | AI insurance coverage analysis | $4.3M seed led by MTech Capital | Feb 2026 |
| Prenosis | AI sepsis risk scoring | $20M Series A led by PACE Healthcare Capital | Jan 2026 |
| Datatruck | Operating system for trucking carriers | $12M Series A led by Avenue Growth Partners | Jan 2026 |
| Xenia | Frontline operations app | $12M Series A from PSG | Nov 2025 |
| Sibel Health | Wireless patient monitoring sensors | Series C extended to $39M | Oct 2025 |
| Empirical Security | Vulnerability exploit prediction | $12M seed led by Costanoa Ventures | Jul 2025 |
| Hoppr | Medical imaging AI data and tools | $31.5M Series A co-led by Kivu Ventures and Greycroft | Jun 2025 |
| CADDi | AI for manufacturing drawings and procurement data | $38M Series C extension led by Atomico | Mar 2025 |
| Sibel Health | Wireless patient monitoring sensors | $30M Series C led by the Steele Foundation for Hope | Mar 2025 |
Established AI companies in Chicago
Several of the city’s best-known AI companies have no new disclosed funding round in this period. Tempus AI, founded by Eric Lefkofsky in 2015, sequences tumors and other samples and applies AI to clinical and molecular data to guide treatment. It has traded on Nasdaq under the ticker TEM since its June 2024 IPO and is headquartered in Chicago.
project44 tracks freight shipments for shippers and logistics companies and has added AI agents to its platform. Its last disclosed round was an $80 million Series G in November 2022, co-led by Generation Investment Management and A.P. Moller Holding, at a $2.7 billion valuation. Uptake, which predicts maintenance needs for truck, bus and equipment fleets, said in March 2026 that Bosch plans to acquire it. Formic rents palletizing, packing and machine-tending robots to mid-sized manufacturers instead of selling them outright.
Health care and manufacturing show up across both lists. Tempus AI, Pathos AI, Sibel Health, Hoppr, Prenosis, KeyCare, ONTO Health and Nara Health all work in health care, and CADDi and Formic sell to manufacturers. For the national picture, see Bot Memo’s top AI healthcare startups and the top manufacturing AI startups.
Who invests in Chicago AI startups
Most of the rounds above were led by firms from outside Chicago, including Atomico, Updata Partners, Battery Ventures, Zeev Ventures, Khosla Ventures and Costanoa Ventures. The Chicago firms below mostly invest at early stages.
- Hyde Park Venture Partners invests from pre-seed to Series A in AI-first applications and infrastructure, and it backed definity’s Series A.
- Hyde Park Angels is an early-stage angel and venture group that was an early backer of Empirical Security.
- Chicago Ventures leads seed and early rounds, with a focus on fintech, supply chain, health care and enterprise software.
- M25 writes pre-seed and seed checks only into startups headquartered in the Midwest.
- Lightbank, a Chicago firm, invested in Letter AI’s Series B, and University of Chicago Ventures invested in KeyCare.
- Illinois Ventures, with offices in Champaign and Chicago, backs deep tech companies tied to the University of Illinois.
- Motivate Venture Capital and Chingona Ventures write early checks, mainly at pre-seed and seed.
1871, a nonprofit startup hub on the 12th floor of the Merchandise Mart, gives founders space and programs. Its name refers to the Great Chicago Fire of 1871. MATTER, also in the Merchandise Mart, runs a health care startup incubator. Argonne National Laboratory, which the University of Chicago operates for the US Department of Energy in suburban Lemont, opened its Aurora exascale supercomputer to researchers in January 2025.
Frequently asked questions
What AI companies are in Chicago?
Chicago AI companies that raised money in 2025 and 2026 include CADDi, Go.AI, Chowbus, Letter AI, Honeycomb Insurance, KeyCare, Empirical Security, Prenosis, ONTO Health, Nara Health, definity, Datatruck, Qumis, Hoppr, Sibel Health and Xenia. Tempus AI, project44, Uptake and Formic are established AI companies in the city. Software company Nerdio and Chicago-founded Pathos AI, which also has offices in New York, raised large rounds in 2025.
What were the largest Chicago AI rounds of 2025 and 2026?
Among the AI companies headquartered in Chicago in this guide, the largest 2026 round so far is CADDi’s $114 million Series D in September, followed by Go.AI’s $85 million Series A and Chowbus’s $81 million round. In 2025 the largest were CADDi’s $38 million Series C extension, Hoppr’s $31.5 million Series A and Sibel Health’s $30 million Series C. Two larger 2025 rounds had Chicago ties: Nerdio’s $500 million Series C and Pathos AI’s $365 million Series D.
Which companies in this guide are valued at $1 billion or more?
Among the AI companies headquartered in Chicago, CADDi was valued at a reported $1.2 billion in its September 2026 Series D, and project44 was valued at $2.7 billion in November 2022. Tempus AI is a public company. Two companies with Chicago ties also passed $1 billion: Pathos AI, founded in Chicago and also based in New York (about $1.6 billion in May 2025), and software company Nerdio (more than $1 billion in March 2025).
Who invests in Chicago AI startups?
Chicago firms include Hyde Park Venture Partners, Hyde Park Angels, Chicago Ventures, M25, Lightbank, Motivate Venture Capital and Chingona Ventures, and Illinois Ventures invests from Champaign and Chicago. Lead investors on the largest recent rounds include Updata Partners, Prysm Capital, Left Lane Capital, Battery Ventures, Zeev Ventures and Atomico.
What is 1871?
1871 is a nonprofit startup and technology hub on the 12th floor of the Merchandise Mart in Chicago. It provides space, community and programs for founders, and it is named after the Great Chicago Fire of 1871.
For how Chicago compares with other cities outside Silicon Valley, see Bot Memo’s ranking of tier 2 AI startup hubs, the full AI startup funding by city breakdown, and the guides to AI companies in Austin and AI companies in Atlanta.
About the author
Editorial Staff
The Editorial Staff at Bot Memo is a team of writers, analysts, and AI agents dedicated to mapping the global AI startup ecosystem. Led by Chintan Zalani, the team tracks thousands of funding rounds, classifies companies across verticals, and distills it all into actionable intelligence for investors and founders.
