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Investor profile

Chicago Ventures

Venture Capital · Founded 2011 · Chicago, United States

Website ↗LinkedIn ↗X / Twitter ↗Dealroom ↗

An early-stage venture capital fund, investing in exceptional entrepreneurs in Chicago

103 portfolio companies Venture Capital · $1.7B invested · 173 investments · Investor rank #1,818 · Last investment 7/2026
Portfolio companies 103 ↑ 16% 5y
Decacorns 0
Thoroughbreds 6
Power Law #274Investor Ranking · Global · 2026 · Top 2%
Featured in
News Buildforce lands $10M Series A to staff electricians nationwide Jul 28, 2026
Estimated holdings

Chicago Ventures’ biggest current holdings.

An estimate of Chicago Ventures’ largest live positions — disclosed shareholding × Dealroom’s latest valuation — across 2 companies where Chicago Ventures is a named shareholder, worth about $248M in estimated equity value.

#CompanyEst. stakeValuationEst. value
  1. 1 Project44Transportation · Unicorn 8% $2.2B $176M
  2. 2 Kin InsuranceFintech · Unicorn 3.5% $2.0B $72M

Estimated value = Chicago Ventures’ disclosed ownership % × Dealroom’s latest company valuation; direct named stakes only, exited positions excluded. Figures are indicative, not reported marks. Chicago Ventures also appears inside investor groups in G2, where a standalone stake isn’t disclosed. See the underlying cap tables on Dealroom →

Portfolio analysis

Where Chicago Ventures’ portfolio is concentrated.

Distribution of portfolio companies by headquarters country, sector, entry stage and current growth stage. Across all 103 portfolio companies. "Stage entered" is the first priced round the investor joined, derived from the investor’s transaction history.

By countryCount
  1. USA99
  2. Canada2
  3. India1
  4. UK1
By sectorCount
  1. Enterprise Software18
  2. Fintech13
  3. Health13
  4. Marketing12
  5. Education7
  6. Food7
  7. Jobs Recruitment7
  8. Real Estate7
  9. Media6
  10. Transportation6
  11. Home Living4
  12. Legal4
By stage enteredCount
  1. Seed67
  2. Series A33
  3. Series B+3
By growth stageCount
  1. Early Growth56
  2. Breakout Stage34
  3. Late Growth13
Portfolio market map

Inside Chicago Ventures’ portfolio.

The 60 highest-funded portfolio companies, of 103 tracked.

Project44
Transportation · Unicorn
$2.2B
Kin Insurance
Fintech · Unicorn
$2.0B
M1 Finance
Fintech · Unicorn
$1.4B
ZenBusiness
Marketing · Unicorn
$1.7B
G2
Marketing · Unicorn
$1.0B
Sunbit
Fintech · Unicorn
$1.1B
Cameo
Media
$100M
LogicGate
Legal
$452M
Data.world
Enterprise Software
$350M
SpotHero
Transportation
$250M
HealthJoy
Health
$240M
OneRail
Transportation
$168M
GreenLite Technologies
Legal
$198M
Havenly
Home Living
$112M
NOCD
Health
$136M
Hint Health
Health
$180M
Shiftgig
Jobs Recruitment
$80M
CoPilot
Transportation
$92M
GoodShip
Transportation
$100M
Catalytic
Enterprise Software
$120M
Visibly
Health
$98M
Veryable
Jobs Recruitment
$128M
Wider Circle
Health
$152M
Curbside
Enterprise Software
$100M
GAN Integrity
Enterprise Software
$60M
Troops
Marketing
$48M
Chowly
Food
$40M
Pangea
Fintech
$41M
eStartAcademy
Education
$120M
Tock
Food
$400M
AeroPay
Fintech
$80M
kapow, inc.
Telecom
$91M
Truss
Real Estate
$60M
Buildforce Services
Jobs Recruitment
$40M
Meritize
Fintech
$53M
pulseData
Health
$66M
healthfinch
Health
$40M
LandscapeHub
Food
$36M
Retrofit
Health
$20M
BloomNation
Telecom
$22M
Dina
Health
$28M
CognitOps
Enterprise Software
$55M
Ureeka
Jobs Recruitment
$43M
Rise Science
Wellness Beauty
$40M
eRelevance
Marketing
$160K
Forager
Transportation
$50M
Infinite
Security
Infinite io
Gaming
$41M
UpCity
Marketing
$26M
Datica
Health
$26M
XOR.AI
Jobs Recruitment
$34M
Oration
Health
$45M
Prisidio
Security
$18M
Predata
Enterprise Software
Blitsy
Marketing
$25M
XOR Data Exchange, Inc.
Fintech
$8.0M
Curiosity
Media
Luxury Garage Sale
Fashion
$12M
BlueTape
USA
$20M
Rocketmiles
Travel
$26M
Portfolio founders

Where Chicago Ventures’ portfolio founders come from.

125 founders across the 100 highest-funded portfolio companies — by current location, university attended, and the companies they worked at before founding. Sourced from the founder records the API links to each portfolio company.

LocationCount
  1. United States103
  2. Canada9
  3. Israel4
  4. United Kingdom3
  5. Argentina1
  6. Denmark1
UniversityCount
  1. The University of Chicago Booth School of Business7
  2. Massachusetts Institute of Technology6
  3. University of Texas at Austin6
  4. Wharton School of the University of Pennsylvania5
  5. Ben-Gurion University of the Negev3
  6. Duke University3
  7. Harvard Business School3
  8. Northwestern University, Kellogg School of Management3
  9. Stanford University3
  10. Stanford University Graduate School of Business3
Previous companyCount
  1. Alphabet | Google3
  2. Guidehouse3
  3. Hewlett Packard Pathfinder3
  4. HP Enterprise3
  5. Accenture2
  6. Architech2
  7. AVG2
  8. Bain & Company2
  9. Bazaarvoice2
  10. Bersin by Deloitte2
How Chicago Ventures stacks up

Similar investors.

Peers the API surfaces as most similar by portfolio shape, with Dealroom investor rank and portfolio scale.

500 Global
Venture Capital · Palo Alto
#430 rank 2,321 companies $289B portfolio
Techstars
Accelerator · New York City
#847 rank 2,278 companies $250B portfolio
Bessemer Venture Partners
Venture Capital · San Francisco
#55 rank 847 companies $1.9T portfolio
SV Angel
Venture Capital · San Francisco
#108 rank 985 companies $3.7T portfolio
Sequoia
Venture Capital · Menlo Park
#3 rank 1,919 companies $22T portfolio
NEA
Venture Capital · Menlo Park
#36 rank 1,186 companies $2.5T portfolio
Y Combinator
Accelerator · San Francisco
#64 rank 7,094 companies $1.9T portfolio
Tiger Global
Private Equity · New York City
#18 rank 811 companies $3.9T portfolio
Figures on this page are sourced live from the Dealroom next-gen API, joined with Dealroom’s cap-table dataset (estimated holdings) and the Power Law Investor Ranking. News in “Featured in” is drawn from Dealroom’s own coverage — the stories that name this investor, not only those it is the subject of. Market sentiment is omitted until the API exposes it.