Funded Artificial Intelligence Startups in Chicago
Disclosed round sizes in Chicago AI skew heavily toward a single outlier: Tempus’ $175M debt financing on 2022-10-20 dwarfs the next-largest disclosed amou…
Disclosed round sizes in Chicago AI skew heavily toward a single outlier: Tempus’ $175M debt financing on 2022-10-20 dwarfs the next-largest disclosed amounts in this set (Evozyne at $81M on 2023-09-27, Letter AI at $40M on 2026-02-24, and HOPPR at $32M on 2025-06-17). At the low end, several rounds cluster near the floor of disclosed amounts, including Tercero Technologies’ $100K pre-seed on 2024-06-18, Speeko’s $150K undisclosed-stage entry on 2023-07-13, and a $100K StratiqAI seed round on 2026-04-01.
The list is temporally concentrated and city-consistent: all 50 rows are Chicago, and the range spans 2020-05-06 (Iris Light Technologies) through 2026-05-29 (Rent Butter). Stage labeling is mixed: 23 of 50 entries show “undisclosed” or “Series Unknown,” while the remaining disclosed stages include notable peaks in the mid-2023 to mid-2025 window (e.g., Evozyne 2023-09-27, Paro 2023-06-14, and HOPPR 2025-06-17).
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Frequently asked
What’s the largest disclosed round in this Chicago AI list, and how much bigger is it than the rest?
Tempus’ $175M debt financing (2022-10-20) is the largest disclosed amount in the dataset, and it sits far above the next-largest disclosed rounds, including Evozyne’s $81M (2023-09-27) and Letter AI’s $40M (2026-02-24).
Are there clear outliers on the low end of disclosed funding amounts?
Yes. Disclosed amounts cluster at small-ticket levels near the floor, including StratiqAI at $100K (2026-04-01), Tercero Technologies at $100K (2024-06-18), and Speeko at $150K (2023-07-13), which are much smaller than the large-ticket rounds like Tempus ($175M) and Evozyne ($81M).
How concentrated are the rounds over time in the 50-row window?
The entries span 2020-05-06 to 2026-05-29, but the most recent half is denser: for example, multiple 2025 rounds (Arvist $4M on 2025-09-20; HOPPR $32M on 2025-06-17; Vermillio $16M on 2025-03-03) sit close to the 2026 entries like Rent Butter ($3M on 2026-05-29) and Letter AI ($40M on 2026-02-24).
Is Chicago the consistent geography here, or do any entries indicate a different city?
Geography is consistent across the visible rows: all 50 entries list Chicago, Illinois, United States (no alternate cities appear in the dataset).
How does the stage/label mix behave: are most rounds tagged with a known stage, or do unknown labels dominate?
Unknown labeling is material: 23 of 50 entries are either “undisclosed” or “Series Unknown” (e.g., BravoTran 2026-05-20 is undisclosed; Kyral 2026-03-04 is Series Unknown), while known disclosed stages include examples like Letter AI (Series B, $40M on 2026-02-24) and Tempus (Debt Financing, $175M on 2022-10-20).
Which set of rounds looks like it clusters in a particular funding-size band?
Beyond the Tempus outlier, several disclosed rounds concentrate in mid-to-large single-digit to tens-of-millions ranges, such as Arvist ($4M, 2025-09-20), Perscient ($4M, 2025-06-11), Vermillio ($16M, 2025-03-03), and HOPPR ($32M, 2025-06-17). In contrast, the smallest disclosed amounts are at $100K–$150K levels (StratiqAI $100K on 2026-04-01; Speeko $150K on 2023-07-13).
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