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Chicago Ventures is an early-stage venture capital firm that primarily leads seed rounds for technology-enabled companies in Chicago and the broader Central U.S.. They focus on being active, operationally-involved partners, often investing in "overlooked teams" across various sectors including enterprise applications, consumer, healthcare IT, and fintech.
Deal activity increased 100% year-over-year (2 deals in the last 12 months). Their most common stage is seed (48% of deals). Average disclosed round size is $27.8M (across 27 rounds with reported amounts).
Portfolio
27
Fund Size
$386M
Top Stage
Seed
Last 12 Mo
2
Portfolio Breakdown
Stage Distribution
Sector Distribution
Investment Activity
DealsAvg Round Size
Portfolio
27 investments
| Company | Round | Amount | Date |
|---|---|---|---|
| IILS | Seed | $3M | Mar 2026 |
 GreenLite | Series B | $49.5M | Sep 2025 |
 AeroPay | Series B | $20M | May 2024 |
| GreenLite | Seed | $8M | Oct 2023 |
 project44 | Growth | $80M | Nov 2022 |
 BlueTape | Seed | $5M | Aug 2022 |
| project44 | Growth | $420M | Jan 2022 |
| AeroPay | Unknown | $5M | Mar 2021 |
 NOCD | Series A | $12M | Oct 2020 |
 Troops | Series B | $12M | Jun 2019 |
| HHealthJoy | Series B | $12.5M | Mar 2019 |
| EEndoGastric Solutions | Series B | $30.5M | Jul 2018 |
 Havenly | Series B | $12.5M | Jan 2018 |
 Kin Insurance | Seed | $4M | Aug 2017 |
| PPluto TV | Series B | $30M | Oct 2016 |
| Troops | Series A | $7M | Sep 2016 |
| PPearachute | Seed | $1.2M | Feb 2016 |
 BloomNation | Series A | $5.5M | Oct 2014 |
| GG2 Crowd | Seed | $2.3M | May 2014 |
| AAgLocal | Seed | $1.3M | Apr 2014 |
 Dónde | Seed | $1M | Feb 2014 |
| BloomNation | Seed | $1.6M | Oct 2013 |
 Curbside | Seed | $1.5M | Sep 2013 |
 SpotHero | Series C | $10.1M | — |
 Leverage | Seed | $7M | — |
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Top Co-Investors
Hyde Park Venture Partners3 shared
Andreessen Horowitz2 shared
Spark Capital2 shared
Great Oaks2 shared
LiveOak Venture Partners2 shared
Felicis Ventures2 shared
The Slack Fund2 shared
Susa Ventures2 shared
First Round Capital2 shared
Emergence Capital2 shared
Insight Partners2 shared
TPG2 shared
Goldman Sachs2 shared
Generation Investment Management2 shared
Sapphire Ventures2 shared
Sozo Ventures2 shared
Founders Fund1 shared
OCA Ventures1 shared
U.S. Venture Partners1 shared
Sidekick1 shared
Last updated: 12 April 2026