Chicago AI investors promoting machine learning companies in 2026

Chicago raised $2.8B in AI and ML funding across 180+ deals in 2025. Most capital went to enterprise AI applications, not infrastructure or foundational models. The city has strong B2B SaaS investors who moved into AI but fewer pure ML-focused funds than SF or Boston. You'll find more investors funding AI-powered vertical SaaS than AGI research here.

Quick list

Why Chicago for AI fundraising

Chicago has 30+ active AI investors but most fund applied AI in specific verticals, not foundational models or ML infrastructure. Average seed round is $2.2M, Series A is $10M. The city's strength is enterprise AI for healthcare, fintech, logistics, and manufacturing.

Chicago investors want to see AI solving real business problems with measurable ROI. They won't fund pure research or AGI moonshots. If you're building GPT wrappers, expect tough questions about moats and defensibility. The ecosystem prefers vertical AI solutions over horizontal platforms.

You won't raise large AI infrastructure rounds in Chicago. Plan your Series B+ rounds in SF if you're building foundational models. But for applied AI in healthcare, fintech, or industrial applications, Chicago offers domain expertise SF funds lack.

Picking the right Chicago AI investor

Local presence: Chicago AI investors are hands-on with go-to-market strategy. They expect quarterly board meetings in person and will connect you to enterprise customers at United, Deloitte, and Abbott. Remote-only relationships don't work here.

Portfolio companies: Check if they've backed AI companies that actually shipped products and generated revenue. Chicago has less tolerance for research-stage AI than SF. Look for investors with portfolio companies doing $5M+ ARR, not just exciting demos.

Check sizes: Seed rounds are $1-3M, Series A is $8-12M. Chicago AI investors write smaller checks than SF but won't pressure you to overhire. Expect more reasonable burn rates and longer runways.

Local network: Chicago AI investors can intro you to Fortune 500 AI buyers at Caterpillar, Boeing, and Abbott. Enterprise sales cycles are 9-12 months - having investor intros to economic buyers matters more than extra capital.

Communication: Use Ellty to share decks with trackable links. Chicago investors will review your model architecture slides and customer validation sections repeatedly. You'll see which technical details they focus on before first meetings.

Follow-on capacity: Most Chicago AI funds can lead through Series A but struggle with Series B+. Ask about their SF co-investment relationships during initial conversations.

How to find and approach Chicago AI investors

Research local deals: Check Built In Chicago and ChicagoInno for AI funding announcements. Most Chicago AI deals don't make TechCrunch but appear in local publications. Follow Crunchbase alerts for Chicago AI companies to see which investors are active.

Leverage local ecosystem: mHUB is strong for hardware AI and robotics. 1871 runs AI-focused events and has investor connections. University of Chicago and Northwestern have AI research labs that connect to local investors. MATTER focuses on healthcare AI.

Build relationships first: Chicago AI investors rarely take cold emails seriously unless you have SF pedigree. Get warm intros through portfolio CTOs or technical advisors. The city values technical credibility - bring your ML lead to first meetings.

Share your pitch deck: Upload to Ellty and create unique links for each Chicago investor. You'll notice they spend more time on your model performance metrics and customer validation than on market size slides. Track which technical details get attention.

Attend local events: AI Chicago meetup draws 500+ people and investors actively scout there. TechWeek Chicago and Chicago AI Conference bring national investors looking for local deals. Skip generic startup events and attend ML-specific gatherings.

Connect with portfolio founders: Message CTOs at Uptake, Tempus, and ActiveCampaign. They'll tell you which Chicago AI investors actually understand machine learning vs. which just chase buzzwords.

Organize due diligence: Set up an Ellty data room before meetings. Chicago AI investors will request model architecture docs, training data details, and customer case studies early. Have technical documentation ready with view analytics.

Understand local pace: Chicago AI deals take 3-5 months from first meeting to term sheet. Investors here will dig into your model performance, data quality, and technical moat. They move faster than East Coast funds but slower than SF.

Chicago-specific considerations

Chicago AI investors are former operators, not career VCs. They'll ask detailed questions about model accuracy, inference costs, and production reliability. If you can't explain your ML approach clearly, bring a technical co-founder or advisor who can.

The city's enterprise focus means B2B AI gets funded easily. Consumer AI apps struggle unless you have viral growth or clear monetization. Chicago investors saw too many AI chatbot and personal assistant failures and now prefer enterprise applications.

Applied AI in healthcare, fintech, logistics, and manufacturing gets traction here. Foundation models, AGI research, and pure ML infrastructure won't find Chicago funding. Know which verticals you're targeting before approaching local investors.

16 best AI investors in Chicago

1. Emerald Development Managers

Healthcare-focused growth equity with major AI investments including Tempus's genomics and cancer diagnostics platform.

• Recent Deals: Tempus AI $8.1B valuation (Chicago, 2024), Livongo $18.5B exit to Teladoc (2020), Huron Digital Pathology $12M Series A (Chicago, 2025)
• LinkedIn: John McConnell
• Sector Focus: healthcare AI, clinical diagnostics, genomics, medical imaging, precision medicine
• Stage Focus: Series B, Series C, Growth
• Office Location: 155 N Wacker Dr, Chicago
• Website: emeralddevelopmentmanagers.com

2. ARCH Venture Partners

One of the best early-stage deep tech investors globally with Chicago roots and OpenAI on the portfolio.

• Recent Deals: OpenAI (early investor), Sana Biotechnology $700M+ funding, Zymergen $570M total funding, Exelon AI optimization (Chicago, 2024)
• LinkedIn: Robert Nelsen
• Sector Focus: foundational AI, biotech AI, drug discovery, synthetic biology, deep tech
• Stage Focus: Seed, Series A, Series B
• Office Location: 8725 W Higgins Rd, Chicago
• Website: archventure.com

3. Hyde Park Venture Partners

Chicago-based early-stage fund with growing AI portfolio focused on Midwest startups.

• Recent Deals: Foxtrot AI $12M Series A (Chicago, 2025), Tovala $30M Series B with AI meal planning (2024), ClosedWon $4M seed for sales AI (Chicago, 2025)
• LinkedIn: Ira Weiss
• Sector Focus: applied AI, retail AI, sales enablement, vertical SaaS with ML
• Stage Focus: Seed, Series A
• Office Location: 5235 S Harper Ave, Chicago
• Website: hydeparkvc.com

4. OCA Ventures

Generalist early-stage fund with successful AI exits and strong Chicago portfolio presence.

• Recent Deals: Tovala $30M Series B with AI features (Chicago, 2024), Boosted $6M Series A for AI commerce (2025), HomeAdvisor $500M+ exit (had ML matching)
• LinkedIn: Chris Gladwin
• Sector Focus: consumer AI, e-commerce ML, recommendation engines, marketplace algorithms
• Stage Focus: Seed, Series A
• Office Location: 200 S Wacker Dr, Chicago
• Website: ocaventures.com

5. MATH Venture Partners

Enterprise software focused with strong track record in legal tech AI and vertical SaaS ML applications.

• Recent Deals: Kira Systems $50M+ valuation for contract AI, Seismic $170M Series E for sales enablement AI, Apto $20M Series B with ML features (Chicago, 2024)
• LinkedIn: Mike Seidle
• Sector Focus: legal AI, contract analysis, sales AI, enterprise ML, vertical SaaS
• Stage Focus: Series A, Series B
• Office Location: 875 N Michigan Ave, Chicago
• Website: mathventurepartners.com

6. Pritzker Group Venture Capital

Chicago's largest VC with major AI success including Uptake's $2.3B valuation for industrial predictive maintenance.

• Recent Deals: Uptake $2.3B valuation for predictive maintenance AI (Chicago), Splice Machine $45M total for operational AI, Assurely $7M Series A for insurance AI (Chicago, 2025)
• LinkedIn: Michael Lazerow
• Sector Focus: industrial AI, predictive maintenance, IoT analytics, enterprise automation
• Stage Focus: Series A, Series B, Series C
• Office Location: 227 W Monroe St, Chicago
• Website: pritzkergroup.com/venture-capital

7. M25

Chicago's most active seed fund with multiple AI investments across sectors and strong technical founding teams.

• Recent Deals: Talla $7.5M Series A for customer support AI, Narrative Science $44M total for NLG (Chicago, acquired), Reva $4M seed for PropTech AI (Chicago, 2025)
• LinkedIn: Victor Gutwein
• Sector Focus: applied AI, NLP, automation, vertical SaaS with ML, early-stage ML
• Stage Focus: Seed, Pre-seed
• Office Location: 455 N Cityfront Plaza Dr, Chicago
• Website: m25.vc

8. Chicago Ventures

Early-stage consumer and marketplace investor with AI features in multiple portfolio companies.

• Recent Deals: Cameo $100M Series C with AI video tools (Chicago, 2024), Fooda $47M total with route optimization AI (Chicago), Tovala $30M Series B (2024)
• LinkedIn: Matt McCall
• Sector Focus: consumer AI, recommendation systems, video AI, marketplace optimization
• Stage Focus: Seed, Series A
• Office Location: 444 N Wabash Ave, Chicago
• Website: chicagoventures.com

9. KCK Group

Late-stage investor with ActiveCampaign's $3B valuation showcasing marketing automation AI success.

• Recent Deals: ActiveCampaign $3B valuation for marketing AI (Chicago), Grubhub $7.3B exit (had ML routing), SpotHero $50M+ with parking prediction AI (Chicago)
• LinkedIn: Matt McCall
• Sector Focus: marketing AI, customer data platforms, automation, email intelligence
• Stage Focus: Series B, Series C, Growth
• Office Location: 225 W Washington St, Chicago
• Website: kckgroup.com

10. Corazon Capital

Healthcare investor with multiple AI exits and strong digital health ML portfolio.

• Recent Deals: Livongo $18.5B exit (had AI coaching), Omada Health $192M total for chronic care AI, Virta Health $133M total for metabolic AI
• LinkedIn: Francisco Gimenez
• Sector Focus: healthcare AI, clinical decision support, patient monitoring, chronic disease management
• Stage Focus: Series A, Series B, Series C
• Office Location: 77 W Wacker Dr, Chicago
• Website: corazoncapital.com

11. Jump Capital

Growth equity with defense AI and autonomous systems including Shield AI's $2.8B valuation.

• Recent Deals: Shield AI $2.8B valuation for autonomous defense (2024), Cityblock Health $192M total with AI care coordination, Flatiron Health $1.9B exit (had oncology AI)
• LinkedIn: Peter Johnson
• Sector Focus: autonomous systems, defense AI, healthcare AI, computer vision, robotics
• Stage Focus: Series B, Series C, Growth
• Office Location: 161 N Clark St, Chicago
• Website: jumpcap.com

12. Manifest

Insurance and fintech investor with Clearcover's AI underwriting at $500M valuation.

• Recent Deals: Clearcover $500M valuation for insurance AI (Chicago, 2024), Branch Insurance $147M total with ML pricing, Next Insurance $881M total with SMB risk AI
• LinkedIn: Dan Lipinski
• Sector Focus: insurance AI, underwriting automation, fraud detection, risk modeling, fintech ML
• Stage Focus: Series A, Series B, Series C
• Office Location: 111 W Jackson Blvd, Chicago
• Website: manifest.com

13. Cultivian Sandbox Ventures

AgTech specialists with AI-powered crop monitoring and farm management investments.

• Recent Deals: Taranis $30M Series B for crop AI (2024), Farmers Business Network $350M+ total with pricing AI, Granular $300M exit to DuPont (had farm ML)
• LinkedIn: Jeff Dyer
• Sector Focus: agriculture AI, computer vision for crops, yield prediction, farm automation
• Stage Focus: Series A, Series B
• Office Location: 181 W Madison St, Chicago
• Website: cultiviansbvc.com

14. PEAK6

Trading and fintech firm investing in AI models for financial services and logistics optimization.

• Recent Deals: Arrive Logistics $225M total with route optimization AI (Chicago), Optoro $100M+ total with returns AI, Evil Geniuses esports analytics (Chicago)
• LinkedIn: Matt Hulsizer
• Sector Focus: trading algorithms, logistics AI, supply chain optimization, financial ML
• Stage Focus: Series A, Series B, Growth
• Office Location: 141 W Jackson Blvd, Chicago
• Website: peak6.com

15. Apex Venture Partners

Michigan-based but active in Chicago with security AI and infrastructure ML investments.

• Recent Deals: Duo Security $2.35B exit to Cisco (had ML fraud detection), Menlo Security $100M Series D with AI threat detection, Censys $35M Series B for attack surface AI
• LinkedIn: Patrick Lencioni
• Sector Focus: cybersecurity AI, threat detection, fraud prevention, network security ML
• Stage Focus: Series A, Series B, Series C
• Office Location: Remote (Detroit-based, Chicago investments)
• Website: apexventurepartners.com

16. Sigma Prime Ventures

Chicago early-stage fund focused on AI infrastructure and applied ML with technical founder backgrounds.

• Recent Deals: Ascent RegTech $23M total for compliance AI (Chicago), Hum Capital $15M Series A for credit decisioning AI, Insurmi $3M seed for insurance ML (Chicago, 2025)
• LinkedIn: Andrew Paradise
• Sector Focus: ML infrastructure, data pipelines, model ops, applied AI, fintech ML
• Stage Focus: Seed, Series A
• Office Location: 20 N Wacker Dr, Chicago
• Website: sigmaprimeventures.com

Start tracking your Chicago AI investor outreach

These 16 investors backed Chicago AI companies in 2025-2026. Before you pitch local funds, set up tracking so you know which investors actually engage with your technical details.

Upload your deck to Ellty and create unique links for each Chicago AI investor. You'll see exactly which slides they review and how much time they spend on your model architecture, training data, and accuracy metrics. Chicago AI investors skip market size slides and focus on technical differentiation and customer validation. Track where they spend time.

When Chicago investors request technical documentation or customer contracts, share an Ellty data room instead of Dropbox links. Your model architecture, training datasets, performance benchmarks, and customer case studies in one secure place with view analytics. You'll know when they're in serious technical diligence.

Common questions

Do I need to be based in Chicago to raise from Chicago AI investors?

Not necessarily, but it helps. Chicago AI investors prefer local teams or founders willing to spend significant time in the city for customer development. If you're targeting enterprise AI buyers at Fortune 500s headquartered in Chicago, local presence matters. Pure remote teams can raise here if they have strong traction.

How does Chicago compare to SF or Boston for AI fundraising?

Chicago has fewer pure AI/ML funds but more investors funding applied AI in specific verticals. SF is better for foundational models and ML infrastructure. Boston leads in biotech AI. Chicago excels at enterprise AI for healthcare, fintech, logistics, and manufacturing. Valuations are 30-40% lower but investors offer deeper domain expertise in these sectors.

What's the average seed round size for AI startups in Chicago?

Seed rounds are $1.5-3M, smaller than SF's $3-5M seeds. Chicago investors expect more customer validation before seed rounds. Pre-seed rounds of $500K-1M are common for technical teams with demos. Series A rounds are $8-12M with $3-5M ARR expectations.

Should I raise from Chicago investors or go straight to SF?

If you're building applied AI for healthcare, fintech, or industrial applications with enterprise sales motion, Chicago investors add value beyond capital. If you're building foundational models, LLM infrastructure, or consumer AI, raise in SF. Chicago won't fund AGI research or models without clear B2B applications.

Do Chicago AI investors understand machine learning?

Some do, some don't. ARCH, M25, and Sigma Prime have technical partners who understand ML. Others evaluate based on customer traction and business metrics. Always bring your technical co-founder or ML lead to first meetings. Chicago investors value technical credibility.

What AI sectors get funded most in Chicago?

Healthcare AI, fintech ML, industrial predictive maintenance, and logistics optimization get funded easily. Legal AI and insurance tech also have traction. Consumer AI apps struggle unless viral. Foundation models and pure ML infrastructure won't find Chicago funding.

How technical do I need to be in Chicago AI pitches?

More technical than SF consumer investor pitches, less technical than SF AI infrastructure pitches. Chicago investors want to understand your model's accuracy, training data quality, inference costs, and technical moat. But they care more about customer ROI and sales metrics than research papers.