Chicago AI startup lands $40M

Feb 26, 2026, 8:00 PM•crainalerts

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February 26, 2026

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1. Letter AI scores $40M as investors eye Chicago AI

2. Springfield inches toward a Bears deal — but Chicago still wants a win

3. State Farm to pay record $5 billion dividend to auto clients

Presented by Valley Bank

Leaders are shifting from maintenance mode to expansion. Latest survey results on risk, investment and smart banking strategy.

4. Why Bally's $250 million casino site is valued at just $43 million

5. Chicago Public Library Foundation names interim chief after CEO's sudden death

Presented by U.S. Bank

Still relying on checks and ACH? How modern payments can unlock cash back and improve cash flow.

6. Pair of professors selling their long-tenured home in Hyde Park

7. Medline's first quarter as a public company ends with rising sales, dip in income

8. Opinion: Chicago can’t afford to lose local news

9. Be in the room with Chicago's most powerful voices

10. Penthouses at $7.5 million-plus will top new Fulton Market towers

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