The Chicago Data Portal is the City of Chicago's open data platform, an early and influential municipal open data program. It publishes operational and geographic data from city departments on a Socrata system.
For mapping it offers boundaries (community areas, wards, census tracts), building footprints, transportation, crime, 311 requests, and many service datasets, exportable as GeoJSON and Shapefile with full APIs. It is the authoritative source for Chicago city data.