The Windy City has a reputation for being down-to-earth, and its investment community is no different. For founders, this means access to capital without the coastal hype.

You'll find active firms like Second Century Ventures, with over 200 investments under its belt, and G Squared, which has guided almost 40 companies to an exit. Many others are writing checks for all kinds of startups.

Below is our list of the best 40 VC firms in Chicago.

Failory's Top 10 Picks

CMT Digital invests in early-stage companies within the crypto and blockchain industry. The firm supports its portfolio through a combination of venture funding, active asset trading, and expertise in the sector's legal and policy issues.

Year Founded2017
FoundersColleen Sullivan, Jan-Dirk Lueders, Scott Casto
Investment StageConvertible Note, Early Stage, Seed
Nº of Investments202 (11 as Lead Investor)
Nº of Exits7 (3 IPO'd)
Contactbitcoin@cmtam.com

S2G Investments backs businesses from seed to late-stage that are transforming the food, agriculture, oceans, and energy sectors. With a portfolio including companies like Beyond Meat and sweetgreen, they focus on building a healthier and more sustainable planet through market-driven solutions.

Year Founded2014
FoundersChuck Templeton, Sanjeev Krishnan, Victor Friedberg
Investment StageConvertible Note, Debt, Early Stage, Late Stage, Post-Ipo, Seed
Nº of Investments182 (83 as Lead Investor)
Nº of Exits9 (4 IPO'd)
Contact312-321-8000

Origin Ventures funds early-stage companies that use artificial intelligence to transform productivity and automation. The firm invests in the infrastructure, software, and marketplaces foundational to this AI-driven shift.

Year Founded1999
FoundersBruce N. Barron, Steven N. Miller
Investment StageEarly Stage, Seed
Nº of Investments125 (51 as Lead Investor)
Nº of Exits21 (1 IPO'd)
Contactinquire@originventures.com
G Squared Logo

4. G Squared

G Squared provides capital throughout a venture's lifecycle, addressing the modern trend of companies staying private longer by offering both growth funding and liquidity for stakeholders. They have backed household names like Spotify, Instacart, and Lyft, partnering with entrepreneurs building disruptive, high-growth businesses.

Year Founded2011
FoundersLarry Aschebrook
Investment StageConvertible Note, Early Stage, Late Stage, Post-Ipo, Secondary Market, Seed
Nº of Investments111 (15 as Lead Investor)
Nº of Exits38 (27 IPO'd)
Contactir@gsquared.com / 312-552-7162

Second Century Ventures promotes innovation in the real estate industry by investing in promising technology startups. As the venture fund of the National Association of Realtors, it gives portfolio companies a distinct advantage through access to the association's vast network and resources.

Year Founded2009
FoundersBob Goldberg, Dale Stinton
Investment StageConvertible Note, Early Stage, Late Stage
Nº of Investments208 (53 as Lead Investor)
Nº of Exits26 (3 IPO'd)
Contacthello@secondcenturyventures.com / 312-329-8524

Sandbox Industries builds and manages businesses by connecting corporate partners with startups in healthcare, food, and agriculture. The firm creates dedicated venture funds and accelerator programs, such as with Blue Cross Blue Shield, to offer entrepreneurs both capital and strategic collaboration.

Year Founded2003
FoundersCecelia Myers, Jonathan Pirc, Nicholas Rosa, Nick Rosa, Robert Shapiro, Ryan Schoop
Investment StageEarly Stage, Late Stage, Private Equity, Seed
Nº of Investments96 (13 as Lead Investor)
Nº of Exits24 (3 IPO'd)
Contactinfo@sandboxindustries.com / 312.228.4656

Impact Engine provides venture capital and private equity to early-stage companies generating positive outcomes in education, health, economic empowerment, and environmental sustainability. The firm supports purpose-driven founders who are building businesses to solve pressing social and environmental challenges.

Year Founded2012
FoundersJamie Jones, Linda Darragh
Investment StageConvertible Note, Early Stage, Seed
Nº of Investments88 (1 as Lead Investor)
Nº of Exits7
Contactinfo@theimpactengine.com / +1 832-265-7550

Wind Point Partners acquires and develops middle-market businesses throughout North America. They build value by executing a strategy that combines initial platform acquisitions with numerous add-on acquisitions.

Year Founded1984
FoundersBob Cummings, Rich Kracum
Investment Stage—
Nº of Investments2
Nº of Exits—
Contactadmins@wppartners.com / 312.255.4800

Chingona Ventures writes checks for pre-seed and seed-stage startups, with a focus on backing founders who are often overlooked by traditional venture capital. They invest in industries like fintech, health, and education, supporting companies such as Career Karma.

Year Founded2019
FoundersSamara Hernandez
Total Funding$58M
Average Check Size$1M
IndustriesFintech, Health & Wellness, Education
Investment StageEarly Stage, Seed, Pre-Seed
Nº of Investments50 (10 as Lead Investor)
Nº of Exits6 (1 IPO'd)
Top Portfolio StartupsBoom, Blanket, Career Karma
Contactadmin@chingona.ventures

With a 17-year track record, Moderne Ventures provides strategic capital to companies from early-stage through private equity. They are generalist investors with deep expertise in sectors like AI, robotics, and enterprise SaaS, backing technologies that can be applied across multiple industries for high growth.

Year Founded2015
FoundersConstance Freedman
Investment StageEarly Stage, Late Stage, Private Equity
Nº of Investments105 (14 as Lead Investor)
Nº of Exits29 (3 IPO'd)
Contactinfo@moderneventures.com

30 Additional Chicago VC Firms Worth Pitching

Chicago's funding scene runs much deeper than our top picks. Combined, the city's other active VCs have backed nearly 2,000 startups and guided over 350 to an exit. This group includes both long-established players and newer funds getting started. Here’s a look at the other venture capital firms funding what's next in Chicago.