Social

http://chicago.metromix.com/ -- A social guide to bars, restaurants, and events in Chicago; up-to-the-minute news on grand openings as well as a great source of info on what's happening in all of Chicago's diverse neighborhoods
http://chicago-scene.com/ -- Chicago's premier entertainment guide; the ultimate authority on who, when, and where it is happening!

City & Local Government

http://egov.cityofchicago.org/ -- City of Chicago official web site. A plethora of information on Chicago such as maps & community info, as well as an un-biased source of real estate news, info, and statistics
http://www.choosechicago.com/ -- Chicago's Convention & Tourism Bureau's official visitor's web site; undisputedly the best site to check out if you are unfamiliar with Chicago and/or are planning a trip here

Real Estate

http://www.chicagorealestatedaily.com/ -- Daily real estate news powered by Crain's Chicago Business
http://www.chicagorealtor.com/ -- Chicago Association of REALTORS®; a member site and association that provides REALTOR® info for its members and the public

News

http://www.chicagotribune.com/ -- Chicago Tribune official web site; Chicago's largest and most respected source of news
http://www.chicagobusiness.com/ -- Crain's Chicago Business; a respected source of business info in Chicago

Financial

http://www.namb.org -- National Association of Mortgage brokers; a member site that also has very reliable up-to-the minute financial information for non-members as well
http://www.iamp.biz/ -- Illinois Association of Mortgage Professionals
http://mortgage.bankofamerica.com/tools.aspx -- Useful financial calculators & tools provided by Bank of America