Funded Apps Startups in Chicago
Disclosed funding sizes in Chicago apps funding are highly top-heavy: ActiveCampaign’s $240M (2021-04-21) dwarfs the next-largest disclosed rounds at $60M…
Disclosed funding sizes in Chicago apps funding are highly top-heavy: ActiveCampaign’s $240M (2021-04-21) dwarfs the next-largest disclosed rounds at $60M (Klover, 2021-08-12) and $50M (Hallow’s $50M appears later, 2023-05-18), with only a small set clearing the $10M mark (e.g., Fly.io $23M on 2026-07-22; NutriSense $25M on 2022-07-13; Veo $16M on 2021-07-13). Timing is also clustered at both ends of the window: rounds span 2020-06-05 (OjaExpress) to 2026-07-22 (Fly.io), while multiple large disclosed events land in the early-to-mid 2020s (2021–2023 includes $240M, $60M, $50M, $25M, and $23M).
Most recent rounds
25 shownRelated listings
Frequently asked
Which app startup funding round is the clear outlier in this Chicago list, and how far above the rest is it?
ActiveCampaign’s $240M round on 2021-04-21 is the largest disclosed amount in the table and sits well above the next-largest disclosed rounds, including Klover at $60M (2021-08-12) and NutriSense at $25M (2022-07-13). The rest of the disclosed amounts generally cluster below that level, such as Fly.io’s $23M on 2026-07-22 and Veo’s $16M on 2021-07-13.
Are there any timing clusters among the most recent entries (e.g., last 12 months in the table)?
Yes. In 2024, several rounds appear close together: HabitNu ($14M) on 2024-03-07, FastModel Sports ($1M) on 2024-03-08, FOODe ($650K) on 2024-04-01, and FieldOS ($530K) on 2024-12-10. In 2026, the most recent entries also cluster: Fly.io ($23M) on 2026-07-22 and Real Sports App ($12M) on 2026-04-13, with Paira ($130K) on 2026-05-08.
How concentrated is the geography within this page?
All 25 rows list Chicago, Illinois, United States, so there is no cross-city dispersion. That makes city-level comparisons irrelevant here, but it does place all outlier funding behavior (like ActiveCampaign’s $240M on 2021-04-21) within the same geography.
What stage or label mix dominates across disclosed amounts, and where are the major exceptions?
Stage disclosure is mixed, but several entries use “Series Unknown” (e.g., Fly.io on 2026-07-22; Real Sports App on 2026-04-13; Foresyte on 2023-10-03; Hallow is explicitly Series C on 2023-05-18). The major exception to smaller rounds is that large disclosed figures are spread across labeled stages too, including ActiveCampaign (Series C, $240M on 2021-04-21) and NutriSense (Series A, $25M on 2022-07-13), not just Unknown.
Do any companies show unusually low disclosed funding compared with the largest rounds?
Service-Plus Connect is the lowest disclosed amount at $50K on 2025-04-08, which is a small fraction of the top disclosed level ($240M on 2021-04-21 for ActiveCampaign). Several other entries fall in the sub-$1M to low-$1M range, such as FieldOS at $530K (2024-12-10) and Real Time Risk Solutions at $800K (2020-10-01), reinforcing the gap between the top-end and the lower-disclosed tail.
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