Chicago, Illinois

Chicago is the third-largest city in the United States — roughly 2.7 million residents — governed by a strong-mayor system under Mayor Brandon Johnson with a 50-member City Council. Enterprise technology direction sits with the Department of Technology & Innovation (DTI), the renamed and reformed central IT agency that sets citywide technology strategy, runs shared infrastructure and networks, delivers cybersecurity, and manages major technology programs for City departments; it is led by a Commissioner who also serves as the City's Chief Information Officer.

Chicago is best understood as a centralized-but-departmental buyer: DTI owns enterprise infrastructure, security, data, and platforms, while large operational departments (Police, the Office of Emergency Management & Communications, Aviation, Water Management, Streets & Sanitation, Public Health) carry their own systems and modernization needs.

The defining backdrop for 2026 is fiscal: the City closed a projected Corporate Fund shortfall of roughly $1.1–1.2 billion and the City Council passed a $16.6B budget in December 2025 — the first in city history crafted by the Council rather than the mayor's finance team — leaving officials warning the result is thin, with forecasts pointing to another large gap (~$1.16–1.3B) for 2027. For a Dell SLG seller this is one of the largest single municipal opportunities in the Midwest; the entry point is DTI's enterprise programs plus the Department of Procurement Services' competitively bid and cooperative vehicles, with most material contracts requiring City Council approval — not a single discretionary IT wallet.

Chicago's 2026 budget was shaped by a large structural deficit. The City forecast a Corporate Fund gap of roughly $1.15B for 2026, and after the mayor's spending plan stalled the City Council passed a ~$16.6B budget in December 2025, which Mayor Johnson allowed to take effect without his signature. The pressure does not ease: forecasts point to another projected shortfall of roughly $1.16–1.3B for 2027, driven partly by rising pension costs (total pension liability reported at ~$36.4B). DTI's own appropriation is funded mostly from the Corporate Fund (~69% of its proposed 2026 budget) with federal grants the next-largest source (~16%); software maintenance and licensing is DTI's single largest expense category — a signal that the application and licensing estate, not new build, dominates the technology line.

• The 2026 budget was the first in Chicago history crafted by City Council members rather than the mayor's finance team; the mayor declined to sign or veto it, and officials cautioned the budget was not fully balanced.
• Fiscal pressure continues into 2027: city forecasts project another ~$1.16-1.3B Corporate Fund gap, with a rising pension bill (total liability ~$36.4B) a major driver — reinforcing a cost-takeout posture for technology.
• DTI's budget skews toward maintaining the existing estate — software maintenance/licensing leads, with notable increases in IT maintenance and legacy telephone (Centrex) billings — pointing to rationalization and refresh conversations over greenfield spend.
• IT spend is partly federated: large departments (Police, OEMC, Aviation, Water) run their own systems and modernization, so verify which department owns a requirement before forecasting.

Selling to Chicago means navigating central procurement and the City Council, not a single buying desk. Competitively bid supplies, equipment, and services run through the Department of Procurement Services (DPS), where the Chief Procurement Officer is the contracting authority and vendors register and bid via the City's eProcurement system. DPS administers master agreements for hardware, software, and technology services via task orders, and the City can use cooperative ('piggyback') contracts to speed sourcing. Material contracts require City Council ordinance approval — build that timeline into any forecast.