Chicago
Metro area · United States · Pop. 10M · #22 city by EV
Largest rounds
Largest funding rounds in Chicago
A live treemap of $100M+ rounds from the Dealroom API. Each cell is one round into Chicago-headquartered companies, grouped by Dealroom sector.
Largest rounds in Chicago - 2026
VC investment
How much venture capital flows into Chicago
VC investment into Chicago-headquartered, VC-backed companies, broken down by round size, company location, sector and funding stage. Live from the Dealroom Next Gen API.
Academia
Chicago's academic flywheel
Companies founded by university alumni or spun out of research, plus the institutions producing the most founders tied to Chicago.
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Notable alumni-founded: PayPal (co-founder)YouTube (co-founder)Yelp
Location comparison
How Chicago stacks up
Compare Chicago with peers from the same country (United States) — switch between combined EV, 5-year EV growth, and a growth × size view. Expand the table for the full ranking.
Combined enterprise value of each ecosystem.
Top cities in United States ranked by combined EV. Chicago's row is highlighted (#9).
| # | Ecosystem | Combined EV | 5-yr EV growth | Unicorns | VC invested | Tracked startups |
|---|---|---|---|---|---|---|
| 1 | Bay Area | $20T | 8.0× | 841 | $156B | 24.7K |
| 2 | Seattle | $2.9T | 4.5× | 68 | $6.6B | 2,951 |
| 3 | Austin | $2T | 14.0× | 58 | $8.1B | 2,499 |
| 4 | New York City | $1.7T | 5.1× | 321 | $32.8B | 16.6K |
| 5 | Boston | $1.2T | 4.6× | 209 | $13.3B | 6,217 |
| 6 | Los Angeles | $1.2T | 5.7× | 151 | $16.3B | 8,475 |
| 7 | Miami | $672B | 13.0× | 39 | $2.6B | 2,754 |
| 8 | San Diego | $332B | 5.1× | 64 | $3.3B | 2,239 |
| 9 | Chicago | $269B | 3.8× | 51 | $2.1B | 2,936 |
| 10 | Washington DC | $264B | 3.3× | 54 | $3.5B | 2,323 |
| 11 | Dallas | $198B | 3.8× | 32 | $1.5B | 1,876 |
| 12 | Phoenix | $136B | 5.2× | 16 | $456.7M | 1,062 |
Premium analytics
What we don't show on this page (yet)
Sector breakdowns, founder origins, AI-talent leaderboards and live deal flow are gated to logged-in Dealroom users. Book a demo to access the full Chicago dataset — or see a sample on the Dealroom app.
More data
Explore Dealroom data →Get the full Chicago ecosystem on Dealroom
Live company-by-company deal flow, full cap tables, founder pedigrees, hiring signals and revenue trajectories.