http://tripsweb.rtachicago.com
The Regional Transportation Authority is the parent agency of the three public transit operators in North-eastern Illinois: Chicago Transit Authority, Metra Commuter Train, Pace Suburban Bus. This site allows one to plot/plan a course from start to finish using all three services.

http://www.transitchicago.com
CTA home page has train (the L) and bus schedules, system maps, service updates and travel planners.

http://www.metrarail.com
Metra Train homepage, includes ticket prices, schedules, and station locations. Can purchase tickets online.

http://www.pacebus.com
Pace suburban Chicago bus home page

http://www.dot.il.gov/road/chicago.htm
Road construction updates from IDOT. Provides estimated start/stop times for projects, impact on travel conditions.

http://www.gcmtravel.com/gcm/home.jsp
Gary IN - Chicago - Milwaukee corridor offers Chicago Quick Traffic, travel times accurate to within 5 minutes. Also provides real-time map of expressway trouble spots.

http://www.chicagobikes.org
City site links to maps of city bike paths. Search by zip code or neighborhood.

http://www.centerstagechicago.com/virtual-el
click on an el stop and this site shows you the bars and cultural activities nearby

http://www.roadragers.com
Does driving bring out your psychotic streak? take test to see if you've got road rage

http://kjo84.typepad.com/cta_tattler
a Chicago based blog that tells of strange doings on the CTA