Funded Information Technology Startups in Chicago
Across the 19 most recent disclosed rounds in Chicago-area information technology startups, Mediafly’s $80M (2023-08-29) is the largest disclosed amount an…
Across the 19 most recent disclosed rounds in Chicago-area information technology startups, Mediafly’s $80M (2023-08-29) is the largest disclosed amount and sits well above the next tier: the only other amounts in the same broad range are K1x at $20M (2024-09-26) and WarpStream Labs at $20M (2024-03-14), while several others cluster far lower (e.g., $2M for Awardspring on 2024-12-16 and $19M for BigScoots on 2023-07-13). Undisclosed amounts appear in 4 of 19 rows (New Era ADR 2023-11-10, Keeper Security 2023-05-09, Udext 2023-04-03, and Sympatic 2022-08-04), and “Series Unknown” appears in 7 of 19 rows (Awardspring 2024-12-16 through oak9 2021-06-02). Date-wise, there is a concentrated run in 2023 (six entries from 2023-04-03 through 2023-11-10), plus a smaller late-2024 cluster (three entries from 2024-03-14 through 2024-12-16). The disclosed amounts span from $100K (Route, 2022-07-11) up to $80M, and the time window for the shown records runs from 2020-05-14 (Forager) to 2024-12-16 (Awardspring).
Most recent rounds
19 shownRelated listings
Frequently asked
What stands out as the largest disclosed round in this Chicago IT set, and how far ahead is it of the rest?
Mediafly’s $80M on 2023-08-29 is the clear outlier; the next-highest disclosed amounts are $20M (K1x on 2024-09-26 and WarpStream Labs on 2024-03-14), while multiple other disclosed rounds sit well below $20M (e.g., BigScoots $19M on 2023-07-13 and Instant Connect $6M on 2024-05-01).
Is there a temporal cluster where funding appears to have concentrated?
Yes. Six of the 19 rows fall in 2023 (from Udext on 2023-04-03 through New Era ADR on 2023-11-10), and there’s also a late-2024 run of three entries (WarpStream Labs 2024-03-14, Instant Connect 2024-05-01, and Awardspring 2024-12-16).
How common are missing round sizes or missing stage labels in these records?
Four of 19 rounds list “undisclosed” amounts (New Era ADR 2023-11-10, Keeper Security 2023-05-09, Udext 2023-04-03, Sympatic 2022-08-04). Separately, “Series Unknown” appears in 7 of 19 rows, including Awardspring (2024-12-16) and K1x (2024-09-26).
Which stage labels dominate among disclosed entries, and what are the notable named stages?
Among labeled stages shown, several rows use explicit labels outside the many “Series Unknown” entries: Fast Radius is “Post-IPO Equity” with $100M on 2022-02-07, BigTime Software is “Private Equity” with $100M on 2022-01-20, and Route is a “Grant” at $100K on 2022-07-11. Pre-seed and Venture-labeled rows are also present (e.g., Super.tech Pre-Seed at $500K on 2021-08-16; Havoc Shield Venture at $4M on 2022-08-05).
Which disclosed amounts are the smallest and how do they compare to the rest of the range?
The smallest disclosed amount is $100K for Route on 2022-07-11; multiple other early-stage or smaller disclosed rounds sit in the same lower band (e.g., Wellspring $450K on 2022-06-24 and Forager $300K on 2020-05-14). That lower end is far from the top at $80M (Mediafly 2023-08-29), with no disclosed amounts between $100K and the mid–high single-digit millions besides the examples above.
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