Funded Apps Startups in Chicago
Disclosed funding in this Chicago “Apps” slice is dominated by one outlier: ActiveCampaign’s $240M Series C closed on 2021-04-21.
Disclosed funding in this Chicago “Apps” slice is dominated by one outlier: ActiveCampaign’s $240M Series C closed on 2021-04-21. The rest of the disclosed amounts sit well below that top line, with the next-largest figures at $130M (Paira, 2026-05-08), $70M (Fly.io, 2023-06-27), and $60M (Klover, 2021-08-12), while several entries are under $1M (e.g., Paira’s $130K on 2026-05-08 vs. Real Time Risk Solutions’ $800K on 2020-10-01).
The entries also cluster heavily in the last ~3 years: 2024–2026 accounts for 9 of 25 rows (Paira 2026-05-08 through FieldOS 2024-12-10), and there’s a second burst in early-to-mid 2022 (DigitalWill.com 2022-12-15, NutriSense 2022-07-13, FoodBoss 2022-02-16). Stage metadata is uneven: “Series Unknown” appears in 7 rows (e.g., Real Sports App 2026-04-13, TrueToForm 2025-06-03) and “undisclosed” amounts appear in 4 rows (TrueToForm 2025-06-03, Eventnoire 2024-08-08, NowSecure 2022-06-09, Pet Enterprises 2022-05-17). Dates span 2020-06-05 (OjaExpress) to 2026-05-08 (Paira).
Most recent rounds
25 shownRelated listings
Frequently asked
What’s the largest disclosed round here, and how sharply does it separate from the rest of the disclosed amounts?
ActiveCampaign’s $240M Series C on 2021-04-21 dwarfs the rest of the disclosed rounds. The next-largest disclosed amounts are $130M (Paira, 2026-05-08), $70M (Fly.io, 2023-06-27), and $60M (Klover, 2021-08-12), with several other companies landing far lower (e.g., $130K by Paira, 2026-05-08; $100K by OjaExpress, 2020-06-05).
Are there noticeable time clusters among the 25 most recent Chicago “Apps” rounds shown?
Yes. There’s a clear recent concentration: 2024–2026 contains 9 of 25 rows, ranging from Paira’s 2026-05-08 round through FieldOS on 2024-12-10 (and multiple entries in 2024, like FOODe on 2024-04-01 and FastModel Sports on 2024-03-08). A second cluster shows up in 2022 with multiple rounds across mid/late 2022 (DigitalWill.com 2022-12-15, NutriSense 2022-07-13, NowSecure 2022-06-09, and FoodBoss 2022-02-16).
How often are stage labels missing or ambiguous, and what does that imply for comparing deals?
Stage precision is limited: “Series Unknown” appears in 7 of 25 rows (e.g., Real Sports App on 2026-04-13 with $12M; TrueToForm on 2025-06-03 with undisclosed; Foresyte on 2023-10-03 with $100K). Separately, the amount is “undisclosed” in 4 rows (TrueToForm 2025-06-03, Eventnoire 2024-08-08, NowSecure 2022-06-09, Pet Enterprises 2022-05-17), which makes cross-deal comparisons harder for that subset.
Where do the extreme low and high disclosed amounts sit within this list’s date range?
The highest disclosed amount is ActiveCampaign’s $240M (2021-04-21). On the low end, the smallest disclosed amount is $12M?—no, among disclosed figures the smallest is $50K (Service-Plus Connect on 2025-04-08) while $100K appears with OjaExpress (2020-06-05) and $130K with Paira (2026-05-08). The timeline runs from 2020-06-05 (OjaExpress) to 2026-05-08 (Paira).
Do any patterns suggest you should treat some entries as outliers beyond just deal size?
Yes—size alone isn’t the only flag. Several rows lack disclosed amounts entirely (e.g., TrueToForm 2025-06-03 and Eventnoire 2024-08-08 are both undisclosed), while the stage labels vary widely, including non-equity formatting like “Debt Financing” for NowSecure (undisclosed, 2022-06-09) and “Convertible Note” for FoodBoss ($800K, 2022-02-16). Those differences mean the list mixes comparable-ish rounds with formats that may not normalize cleanly.
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