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A few current Chicago maps:

Loop map 2010

Downtown Chicago
courtesy of Chicago CartoGraphics

downtown pedway map 2015

Downtown Chicago pedway and cut-throughs

courtesy of Chicago CartoGraphics

downtown pedway map 2015

Chicago area expressways and traffic report names

courtesy of Chicago CartoGraphics

leaf-off aerials 2005

2005 aerial photos at Illinois State Geological Survey
late spring (leaf-off) aerials so streets and structures can be seen in wooded areas

leaf-off aerials varies

USGS topographic maps online
choose t4 Topo High in upper right corner

leaf-off aerials 2011

Chicago bike map online
bicycling facilities and routes shown on Chicago CartoGraphics base map

CTA train map 2015

Chicago rapid transit map
all routes, even the crowded Loop, integrated into a simplified map


Transit isochrones
how far you can get by transit in a set amount of time

Home prices
data from Trulia

Public art
outdoor installations in the City of Chicago


nationwide map of where jobs are located

City of Chicago 80-acre cadastral map viewer
alternate search by PLSS section

neighborhood map 2014

Chicago neighborhood map
A map of neighborhood boundaries is inherently problematic, for reasons described here.
But if you're determined to have one, this 2008 PDF from the city seems as good as any.

street guide 2014

Chicago street guide
PDF showing all Chicago streets with house numbers (2600 N, etc.)