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1.
Chicagoland is the area bound by Chicago and all of it's suburbs. It goes as far as University Park, Matteson, Sauk Village in the south, Joliet in the southwest, Plainfield, Naperville, Geneva, Batavia in the west, Elgin in the Northwest and the Waukegan area in the north.

Chicagoland is huge and everyone seems to know eachother.
I don't live in Chicago, but I live in Chicagoland.
by ChrisAlx33 August 01, 2004
 
2.
Chicagoland is a term that carries several common misconceptions. It is believed by many people (usually living in the northern and western suburbs of Chicago) that Chicagoland, or more formally the "Chicago Metropolitan Area" is restricted to only the areas within the Illinois state boundaries. However, due to the fact that a metro area is based on cultural and employment patterns and similarities, this is simply not true.

Because Chicago is such a large city on its own, it boasts a much wider metro area than most others in the country, save for New York and Los Angeles. Dating back to 1950, when statistical analysis for metro areas emerged, Chicagoland included several counties in Illinois (Cook and the adjacent counties such as Will, Lake, and DuPage) as well as Lake County in Indiana which to many a-Chicagoan's surprise physically borders the city. Over the years, due to Chicago's expansion, the definition has also widened to include four more Indiana counties (Porter, LaPorte, Newton, and Jasper) as well as Kenosha County in Wisconsin.

This phenomena is not unique to Chicago, and examples can be seen all throughout the U.S. New York City - New Jersey, St. Louis - southwestern Illinois, Kansas City - western Missouri, and many more. So before you let silly biases like state lines get in the way, remember to check your facts!
As I mentioned above, a metro area is not determined by state lines, but by a shared culture. For example, the types of cuisine unique to Chicago can be found all around Chicagoland. Things like the Chicago Hotdog, the Maxwell St. Polish, Italian beef sandwiches, deep dish pizza, and etc. Other examples include the commuter culture, or the people who travel into the city for work; favorite sports teams; dialects and slang; time zones (Northwest Indiana shares a time zone with the rest of Chicagoland, and not the rest of the state).
by WoodmarBoy March 03, 2014