The major cities of the region are, well, Chicago — period. None of the outlying cities remotely approach the size of this mammoth metropolis. In fact, all besides Chicago have populations under 200,000. But that's not to say that Chicagoland doesn't include other destinations; some of the larger cities include:
Cook County, where Chicago is located, is the largest county by population in Illinois and the second-largest in the United States (after California's L.A. County). With more than 5 million residents, its population is larger than that of most U.S. states; a little more than half of them live in the central city, with the rest in a chain of suburbs that surrounds Chicago on the north, west and south sides.
Evanston, the first city north of Chicago along the lake, is home to Northwestern University. Other communities along Cook County's affluent North Shore are:
Glencoe, home to the famous and much visited Chicago Botanical Gardens
Just how much territory is covered in the term "Chicagoland" is a point of controversy. Certain surrounding counties in Wisconsin and especially Indiana have enormous commuter populations, which share Chicago's regional culture, and it is hard to exclude them.
Lake County, Indiana, a highly industrialized and densely populated section of Lake Michigan's shoreline, represents some of the poorest suburban areas and satellite cities in Chicagoland. Gary in particular has fallen on extraordinarily hard times, and has one of the highest violent crime rates in the country. Once upon a time the city was an industrial giant, and was an urban center in its own right, but today an ever increasing number of Gary residents commute towards Chicago for employment. And in terms of culture, Lake Co. is solid Chicagoland territory, from hot dogs to the blues. Other major population centers in Lake County include:
Some residents of Kenosha consider the Chicagoland denotation controversial, as it is closer to Milwaukee. But nonetheless, there is a much bigger commuter population to Chicago. Metra, the suburban train system, has a route from downtown Chicago to Kenosha. The federal government considers Kenosha part of the CSA of the Chicago metropolitan area.
Chicagoland is huge; it is one of the world's largest metropolitan areas both in terms of population and area.
The Forest Preserve District of Cook County is responsible for the numerous open spaces ("forest preserves") around the county. These preserves range from heavily used parks with extensive roads and well-developed picnic areas, to relatively isolated expanses of land that are only really accessible on foot (or cross-country skis in winter).
The Pickwick in Park Ridge is one of the true grand movie palaces remaining in the Chicagoland area.
Ribfest in Naperville is one of the largest festivals in the county.
The annual Eyes to the Skies Balloon Festival in Lisle.
The Illinois Prairie Path runs through the center of DuPage County.
For all intents and purposes, Chicagoland is Chicago when it comes to food. You don't need to head into the city proper to get your Chicago-style pizza, hot dogs, beef, steaks, and what have you. There are some Chicago-style fast-food locations outside the city that will serve you these items, prepared better than anywhere in the city. Same goes for many styles of ethnic food—you can get Mexican, Polish, Italian, Greek just as good or even better in the 'burbs. Some ethnic cuisines out here you would have trouble finding in the city—Uzbek, Russian, Afghan, etc.
For upscale cuisine, the hautest of the haute is still to be found downtown. But there are plenty of nice restaurants in places like Evanston (especially), Naperville, and others.
The Chicago Tribune ("The Trib") is the Chicago area's biggest daily, and publishes a suburban edition.
The Chicago Sun-Times The other major Chicago paper, long-time rivals with the Tribune.
The Daily Herald is a large daily newspaper aimed primarily at the suburbs.