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Come on,
Oh baby don't you wanna go,
Back to that same old place—
Sweet home Chicago!

Chicago, Illinois: incorporated in 1837. The name comes from the Algonquian word shikaakwa, or "wild onion"note . We kid you not: it was what was growing in the swampland around Lake Michigan that was perfectly situated for continental-scale commerce.

We kid you not about the "perfectly situated" part either. The Great Lakes lie in a separate watershed from the Mississippi River, specifically that of the St. Lawrence River. While the divide between the two watersheds isn't exceptionally high, it was still a formidable barrier for water transportation... except at this one specific point. For thousands of years before white explorers and settlers arrived, the local Native Americans used a six-mile passage now known as the Chicago Portage to move between the two watersheds. During wet periods, they could travel the entire passage by canoe; at other times, they would have to drag their canoes and supplies through at least part of the area. Still, this was the only (relatively) easy means of water transport between the two watersheds before the arrival of white settlers, who eventually built a canal through that area.note  This led to a massive period of growth, as the city was now the central hub of trade and transit for the whole country. The rise of the railroads only accelerated this trend, as practically every railroad ran a line into Chicago; even to this day, Chicago is the center of the U.S. rail network, with all six Class I freight railroads in North America (BNSF, Canadian National, CPKC, CSX, Norfolk Southern, and Union Pacific) serving the city.note  The city was leveled by a massive fire in 1871, widely suspected in Urban Legend of having been started by a cow, which killed 200-300 people.note  It built back even stronger; by the end of the 19th century, it had surpassed Philadelphia as the nation's biggest city behind only New York City.

Today, Chicago is the third most populous city in the United States, having been surpassed several decades ago by Los Angeles. It is still the urban hub of the Great Lakes region and a fabled fortress of jazz, organized crime, Michael Jordan, Daaaaaa Bearsss, the 1893 World's Fair, deep-dish pizza, Frank Lloyd Wright, house music, improvisational theatre, pinball, lots and lots of drawbridges, two baseball teams known for perennial mediocrity which fiercely battle for the city's love/scorn, skyscrapers, revolving doors, note  a very pleasant lakefront, very unpleasant winters, the 44th president, and a certain roughneck Midwestern charm. Its nickname of "The Windy City" was coined by Charles Dana of the New York Sun to dismiss Chicago politicians who promised that it would be awesome if they got the World's Fair in 1893 as being full of hot air. (They got the fair, and it was indeed awesome.)note  During the Prohibition period, it was the home base of Al Capone. Blacks fleeing the Jim Crow south made it a blues center. A squash court at the University of Chicago was the site of the world's first controlled nuclear reaction.

Chicago has a public rail system called the 'L,' a combination of subways and elevated tracks that radiates from a loop around the city center towards the city's edges and (in some cases) the surrounding suburbs. This "Loop" runs through some of the most prominent buildings in the city, including the Willis Tower (which most Chicagoans will tell you is the Sears Tower, the third tallest building in the Americas behind only CN Tower and One World Trade Center; the retail company had moved out long before it was renamed for Willis Group Holdings, Ltd.). Contrary to the popular belief, the Loop got its name from the now-gone cablecar loop rather than the elevated rail tracks that encircle it today. Also, the system is called the 'L', not the "El" (that would either be elevated parts of the NYC Subway or the Market-Frankford Line of Philadelphia's rapid transit system). Metra provides commuter rail service throughout Chicago's suburbs, with trains coming into one of four different downtown terminals. Chicago is also the Midwest hub for Amtrak, and is where a large assortment of long-distance trains start or end their trips, along with a variety of regional services that provide intrastate service within Illinois, Indiana, Wisconsin, and Michigan.

The vast majority of Chicagoans live, play, eat, and occasionally murder in Chicago's many, many neighborhoods. People call Chicago "a city of neighborhoods," with each having their own distinct character and well defined boundaries. Many current-day neighborhoods were originally cities or suburbs on their own that Chicago swallowed up as it grew. Many of these cities kept something of their previous character, even unto today.

The Chicago sprawl has over a hundred neighborhoods organized into several Sides. Most people are familiar with the North and South sides. The North Side is commonly depicted as wealthy and white while the South Side is usually depicted as poor and black. There is a certain truth to those assumptions—the North Side contains some of the city's wealthiest neighborhoods, while the South Side contains some of the city's poorest, most crime-ridden ghettos. But as most Chicagoans would tell you, there are plenty of exceptions—North Side has its share of poor and working-class neighborhoods with fairly diverse immigrant population (Uptown and Rogers Park immediately come to mind), and South Side has its share of working-class, middle-class and even wealthy neighborhoods (Hyde Park, Kenwood, Bronzeville and Beverly). The reason why the perception exists is because historically, the North Side was wealthier than the largely working-class South Side, due to one of the earliest and perhaps most ironic cases of what would eventually be termed "white flight", when wealthy Protestant English-descent Americans moved to the north side, away from... other whites, namely immigrant Catholic Irish and Germans. Also:

North Side: "GO CUBS!" South Side: "GO WHITE SOX!"

For the love of God, don't get those two confused.

In addition to North Side and South Side, there are several other lesser-known sides: West Side, Northwest Side, Southeast Side, Far Northwest Side, Far South Side, and the neighborhood known as the East Side.

The greater Chicago metropolitan area is called "Chicagoland" by locals.

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    North Side 
North Side: A historically working class area with a few wealthy enclaves here and there, it has recently seen some gentrification efforts on all sides. The wealthy neighborhoods are concentrated in the Near North Side—the city's original northern section that begins at the Chicago River and ends at North Avenue. Some of the more notable neighborhoods include:
  • Gold Coast: One of the wealthiest neighborhoods in Chicago and, for a while, the only wealthy neighborhood in the Near North Side. It is made up of a peculiar mix of high-rises and small yet expensive rowhouses (plus a few historic mansions here and there).
  • Streeterville: Established by Civil War veteran George Streeter on the landfill formed by the debris created during the Chicago Fire, it was an industrial neighborhood for much of its existence. In recent decades, it saw some very heavy-duty gentrification as high rises were built where warehouses and factories once stood—today, it is home to some of the most expensive real estate in Chicago.
  • Cabrini-Green: A public housing complex infamous for its crime and poverty, it is currently undergoing slow and painful forced gentrification as the decaying public housing buildings are slowly being replaced by mixed-income housing. One of the more common geographical mistakes when it comes to Chicago is placing Cabrini-Green on the South Side. It is actually in Near North Side, to the west of Gold Coast. In 1981, Mayor Jane Byrne, in order to put her money where her mouth was in terms of cleaning up Chicago, moved her and her husband's personal residence into the Cabrini-Green complex; this backfired, with Byrne leaving after only three weeks, and the fortifications that the Chicago police had installed in her unit wound up being used by gang members to turn said unit into a bunker. (Worse, they later copied those fortifications in other units.)
  • River North: Another former industrial area, it got a new lease on life as Chicago's oldest artist colony. These days, the poor artists that defined it either got rich and stayed put or moved elsewhere. Most of the people that lived here now fall into upper-middle class, but its artistic legacy survives in its art galleries.
  • Magnificent Mile: One of Chicago's three original high-end shopping districts, it was the only one to survive to this day. Currently the classic department stores have been outed by typical mall shops and a few museums still spot it. A water tower built in 1869 is a prominent landmark here.
  • Lincoln Park: One of the poster children for North Side gentrification, it was originally a working-class neighborhood dominated by (in chronological order) Germans, Poles, and Puerto Ricans. These days, it's largely middle class, with the coastal area threading towards "wealthy." The neighborhood is also home to the main campus of DePaul University, the second-largest university in the city (after UIC).
  • Lakeview: Another former working-class neighborhood, this area houses Boystown and Wrigleyville. Contains the goth- and hipster-friendly Alley shopping complex and lots of overpriced apartment buildings.
    • Boystown: The latest in the long line of Chicago's gayborhoods (and so far, the longest-lasting), it developed along the Chicago Pride Parade route. Gentrification has eroded some of its GLBT-centric aspects, but only to a point.
    • Wrigleyville: Exactly What It Says on the Tin, this section of Lakeview is the area surrounding Wrigley Field, home of baseball's Chicago Cubs, who are notable for being the only team that still plays the majority of their home games during the daytime. This has an effect on the culture of the surrounding area, which is loaded with bars: Cubs fans tend to show up after the game is done in the late afternoon or early evening, and on the weekends they stay as long as they can (Wrigleyville has a large number of bars with licenses to go as late as 4 AM if not later). The apartment buildings across from Wrigley on Waveland and Sheffield Avenues have been expanded to become part of the field's seating unofficially, though they have to pay the Cubs a premium for the privilege.
  • Uptown: One of the North Side's historically wealthy neighborhoods and home to what was then the city's largest entertainment district, it was hit pretty hard during the Great Depression. After World War II, it became a refuge for ethnic and social groups that had hard time settling anywhere else on the North Side. There have been some efforts to gentrify Uptown, and they were somewhat successful, but much of Uptown is still either working-class or poor. These is lots of back-and-forth between the gentrifiers and everybody else about what the neighborhood is like and what needs to be done in order to fix it. Taking any position on the matter will cause flame wars.
  • Edgewater: Originally Uptown's wealthier section, it broke away to make a fresh start. Gentrification has been more successful here, though as with Uptown, it didn't completely take. It has a sizable immigrant population, and many of those immigrants came from African countries.
    • Andersonville: A historic Swedish neighborhood, it developed a sizable lesbian enclave back in The '80s. During the most recent real estate boom, it was heralded as the Next Hip Thing, but while it never did become the next Lakeview, it lived up to the label in many respects.
  • Rogers Park: A former site of a major Pottawatomie Indian settlement (part of its boundary line, as defined by a 1816 treaty, is now Rogers Avenue), the neighborhood has become a haven for immigrants from all over the globe, including India, Pakistan, Russia, Ecudaor, Korea, China and various Middle Eastern countries. It is one of the few Chicago neighborhoods that can be safely called "integrated." The section closest to Chicago's northern border (locally known as Juneway Terrace or, less charitably, Juneway Jungle) is fairly poor, but the rest of the neighborhood is largely working class, with some middle-class incursions along the coast and near Loyola University. (North of the city limits here lies Evanston, an old college town.)
  • West Ridge: The western section of Rogers Park back when Rogers Park was an independent village, it shares many characteristics with its parent community, except it has less gentrification, more immigrants and less genuinely poor areas.

    South Side 
South Side: Once the wealthiest section of Chicago, its fortunes took a dramatic turn for the worse in the wake of the Great Depression. It also contained the city's largest black enclave—Bronzeville. Any black resident who tried to settle outside of its borders was not looked upon very kindly (to put it mildly). When the U.S. Supreme Court made housing restrictions illegal and black people spread out beyond the overcrowded Bronzeville, white residents panicked. There were some attempts to stop the process, but ultimately, the older residents couldn't fight demographics. Most chose White Flight. Red-Lining and blockbusting made things worse for the black residents that replaced them.

For a while, the South Side contained the largest concentration of public housing in United States (mostly because white aldermen didn't want it in their neighborhoods and fought to keep it in Bronzeville's immediate vicinity). From the late 1980s onward, the city has been tearing them down and replacing them with mixed-income housing. Or, at least, that's the theory—the replacement part has been kind of slow. There has also been some gentrification going on, mostly in the Near South Side (the city's historic southern section).

Some of the more notable South Side neighborhoods include:

  • South Loop: Once an enormous network of docks, rail yards, factories, and storage facilities, the area immediately south of the Loop is being transformed beyond recognition as high-end development after high-end development is built. The Central Station development, which was built near a demolished eponymous rail terminal, contains some of the most expensive buildings in the city.
  • Chinatown: Originally a South Italian neighborhood, it has been home to Chinese immigrants since the 1920s. Overcrowded, incredibly touristy, but nonetheless pleasant, it is trying to strike a balance between serving the needs of its residents and attracting visitors.
  • Bridgeport: Chicago's first Irish neighborhood and the heart of the city's legendary Democratic machine. A longtime bastion of European immigrants and their descendants, the neighborhood has seen significant influx of Chinese and Mexican residents, to the point where they operate a significant portion of the neighborhood's businesses. For a while, blacks weren't particularly welcome there, even after the civil rights era, but that is gradually changing.
  • Bronzeville: Chicago's oldest black neighborhood (the widely-circulated Chicago Defender was published here), it has recently become a site of major redevelopment efforts as the middle-class descendants of its original residents hope to transform it into a safe, bustling black community. North of Pershing Road, things look like they are heading in that direction—south of it, not so much.
  • Armour Square: Sandwiched between Bronzeville and Bridgeport, this is where baseball's White Sox have played every one of their home games since 1910. Though historically most of its inhabitants have been Croat and Italian, today Asian Americans outnumber the white population by nearly six to one.
  • Hyde Park: A neighborhood that exists in symbiosis with the University of Chicago, which invested considerable money and resources into making sure that it wouldn't succumb to economic depression and decay the way most surrounding neighborhoods did. It is one of the few Chicago neighborhoods that can be considered integrated, but, as many have bitterly pointed out, most of the residents are middle-class. Hyde Park and the U of C enforce the peace with very heavy police presence and an extensive emergency alert system. Hyde Park is also home to the expansive Museum of Science and Industry, which contains, among many other things, the German submarine U-505 (captured by the US Navy in 1944) and the Pioneer Zephyr (the first diesel-powered streamlined passenger train).
  • Kenwood: A historically white, middle-class neighborhood, it has been going through a process similar to Bronzeville, except in this case, it went on for almost a decade longer and had more successes. Some of Chicago's wealthiest and most famous black residents live here (including Barack Obama, who moved in from Hyde Park in 2005). As with Bronzeville, the development has been uneven—it's a solidly middle-class black enclave south of 47th Street, but things get a lot more mixed in the rest of the neighborhood.
  • Englewood: One of Chicago's most dramatic falls from grace, this was once a wealthy neighborhood with a thriving shopping district at par with Magnificent Mile. The Great Depression took a heavy toll on it, and it has only gotten worse since. Today, its shopping strip is virtually abandoned, the once-majestic homes are decaying and the population shrinks every year. After most South Side housing projects were demolished, Englewood became one of the most crime-ridden neighborhoods in Chicago by default. There have been lot of redevelopment and gentrification attempts, but nothing took.
  • Back of the Yards: Former site of the Union Stockyards (which, in turn, figured prominently in The Jungle). Originally dominated by Poles and other Eastern European immigrants, it became a Mexican-American neighborhood in The '70s.

    Far South Side 
Far South Side: Often conflated with the South Side, this section of Chicago is more recently developed and, historically speaking, was largely working class. Its fortunes are tied to the factories around Lake Calumet and adjacent bodies of water. When the South Side took a turn for the worse, this area was regarded as a preferable alternative, and many blacks of all economic levels were able to live comfortably here. Unfortunately, the Lake Calumet industrial region has been slowly but surely falling apart since the 1970s. The persistent pollution has only made things worse, and when public housing was demolished en masse on the South Side, many of the former residents headed for Far South Side's working class neighborhoods, bringing their criminal histories and rivalries with them. Although many communities are still holding on, others have taken the turn for the worse. Some of the more notable Far South Side neighborhoods include:

  • Chatham: A middle-class enclave since the 1920s, it transitioned from a white majority to a black majority with little difficulty. Its shopping areas are spotty at best, but the residential homes are pretty nice. While there is some concern about the rising crime, crime rates still pale in comparison to the greater South Side averages.
  • Beverly: A former luxury resort for the wealthy, this distant neighborhood redefined itself as one of Chicago's few remaining Irish neighborhoods. Its residents fought against White Flight and blockbusting while trying to make blacks feel welcome. The resulting neighborhood is similar to Hyde Park, except with better architecture, a more suburban atmosphere and significantly less police presence—less on-duty presence, that is. A large number of police officers make their homes in Beverly.
  • Calumet Heights: Founded by railroad workers, this working-class neighborhood transitioned to black majority pretty late in the game (1970s-1980s). It's fairly safe and reasonably comfortable. Pill Hill, an upper-class black enclave, is located right in the middle of it.
  • Pullman: A company town built by George Pullman, a rail car magnate, it was supposed to be an ideal workers' settlement—except George Pullman was an authoritarian prick who didn't mind screwing his employees over. The whole thing ended in a 1894 strike that had to be put down with federal troops. Since then, Pullman has been a working-class, multiracial neighborhood that is fairly safe, yet fairly isolated—a few restaurants, virtually no businesses and no entertainment venues to speak of. Local residents are trying to turn the now-abandoned Pullman factory complex into a museum, but lack of money slows the process to a crawl.
  • Mount Greenwood: A predominantly Irish-Catholic neighborhood (in fact the fourth most Irish neighborhood in the country), it's populated almost entirely by Chicago firefighters and police officers, since it's the farthest from the center of the city a public worker can live without losing his/her job. It has a very strong church presence and contains several private Catholic schools, including Mother Mcauley, the nation's largest all-girls high school (and its sister school Brother Rice, one of the largest all-boys schools), as well as the Catholic university Saint Xavier University. It's also the only one of Chicago's 77 community areas which was counted for Donald Trump in the 2016 election.
  • East Side and Hegewisch: Two neighborhoods that each share a border with the adjacent state of Indiana (you can actually see Gary from there), these working class communities are isolated from the rest of Chicago by Lake Calumet and the Calumet River to the north and west. Many native Chicagoans don't even realize they exist. The two communities traditionally had large Eastern European populations until the late 20th century, when increasing numbers of Mexican immigrants began moving into the area. East Side and Hegewisch don't have that much to offer other than relative peace and quiet.

    West Side 
West Side: An area that was long dominated by factories and working-class neighborhoods, the West Side fought integration kicking and screaming, to no avail. When Martin Luther King Jr. died, the riots ravaged most of the side's business areas, something from which it has never quite recovered. The departure of manufacturing jobs only made things worse. Taken at large, West Side is poorer than the South Side, though it's also a bit more diverse. There has been some fairly aggressive gentrification going on in the area's eastern section. Its notable neighborhoods include:

  • West Loop: The heart of the old manufacturing district, this area received a lion's share of West Side gentrification—given that not a whole lot of people lived there to begin with, it didn't receive that many complaints. There is no consensus as to just how far it extends, though most can agree that it probably stops at some point before Ashland Avenue. The neighborhood contains Oprah's Harpo Studios and a museum of holography.
  • Greektown: A neighborhood established when the original Greektown was torn down to make way for what is now the University of Illinois at Chicago's East Campus. Most of Chicago's Greek-Americans technically live elsewhere in the city, but they do maintain a decent shopping district and a fairly neat museum here.
  • Little Italy: One of Chicago's oldest Italian neighborhood, it is best known for its variety of restaurants and a couple of neat churches. It was once home to Jane Addams Homes, the oldest public housing development in the city.
  • University Village: A neighborhood created when UIC demolished the old Jewish ghetto of Maxwell Street to pave the way for its South Campus. Lots of Chicagoans are still bitter about it. The neighborhood used to be home to Maxwell Street Market, the city's biggest flea market, but it has since been moved a a few blocks northeast.
  • Pilsen: Originally established by the many ethnic groups that lived in Austria-Hungary, this working-class neighborhood has since become the city's oldest Mexican neighborhood. The eastern section has seen some gentrification and a burgeoning artist colony. The neighborhood dealt with some major gang problems back in the 1990s, but things have quieted down (mostly).
  • East Garfield Park: A poor neighborhood without much to offer except for the eponymous park, which has a pretty neat conservatory. There have been many attempts to gentrify it, but so far, none of them really took. Not to be confused with the more dangerous West Garfield Park.
  • Little Village: Historically a Central European enclave of Poles, Czechs, and the like, this is today the heart of Chicago's Mexican-American community. The neighborhood hovers between working-class and poor; it has a decent commercial district centered on 26th Street (if you want an authentic Mexican meal or any kind of Mexican product, go to 26th Street—you'll find it) and lots of community organizations, but it also suffers from sizable gang activity that occasionally escalates into full-fledged violence. It doesn't help that the Cook County Criminal Courthouse and Jail are in this neighborhood.
  • Austin: Chicago's largest neighborhood, this historically middle-class community fell on hard times in 1970s. Things haven't gotten much better since. It has one of the highest crime rates in the city, though the sheer size of the neighborhood is probably skewing the figures. It is also home to the only Walmart to ever be opened within Chicago city limits.
  • Near West Side: Can refer to the collection of west side neighborhoods nearest The Loop as a whole, but more commonly known for the area between the West Loop, University Village, and Medical Village that includes United Center, home of the Blackhawks and Bulls. Former location of United Center's predecessor, the Chicago Stadium, which is regarded as the loudest sports venue in historynote , most notably the 1991 NHL All-Star Gamenote .

    Northwest Side 
Northwest Side: A largely working-class area that is often grouped with either North Side or West Side (or both). For much of the 20th century, its population was largely Polish with significant Jewish, German and Italian components, but these days, it is mostly known for some fairly aggressive gentrification attempts. During the height of the most recent real estate speculation, virtually every neighborhood was seen as the next Wicker Park and everybody was looking to jump on the bandwagon. While some neighborhoods would up living up to the hype, most didn't—at least not yet.

  • Wicker Park: Originally a middle-class neighborhood settled by Germans and later Poles, it became a Puerto Rican working-class neighborhood by the 1970s. When the fire swept through River North in 1991, many artists wound up moving to Wicker Park and, before you knew it, it became a magnet for emerging artists. These days, it is thoroughly gentrified, overwhelmingly hip and yet surprisingly diverse—it's just that most of the new residents have middle-class income.
  • Bucktown: Wicker Park's historically working-class sister neighborhood. When Wicker Park's popularity took off, many artists went to Bucktown, only to find that gentrification followed in their footsteps. It isn't quite as thoroughly gentrified as Wicker Park, but depending on which way the economy goes, this may or may not be true in a few years.
  • Ukrainian Village: One of the longer-lasting, most stable ethnic communities in Chicago, this neighborhood has lots of beautiful churches and decent Ukrainian stores. The eastern section has become an entity in its own right as the significantly more gentrified East Village.
  • Logan Square: A working-class, largely Puerto Rican and Mexican neighborhood, it has reasonable rents, a decent shopping district and surprisingly high crime rates (at least compared to other areas). There is some gentrification/general yuppie immigration in the corridor down Milwaukee Avenue between the California and Logan Square 'L' Stations. Also plays home to Bucket O' Blood Books And Records, a book/record store owned by Marc Ruvulo, the owner of legendary local punk label Johann's Face.
  • Albany Park: Another significant immigrant enclave, this neighborhood plays hosts to over eighty ethnic groups; it is not only one of the most diverse neighborhoods in Chicago but the whole country. Most of the local businesses are either Mexican or Korean, which leads people to assume that they make up the majority (they don't). There's some gentrification at the edges in areas with good access to the Brown Line (which terminates here).
  • Ravenswood: A working class neighborhood that owes its existence to the Ravenswood branch of what is now the Brown 'L' line. Has lots of apartment buildings and quite a few pockets of gentrification; the gentrified pockets are extremely gentrified (Rahm Emanuel, the former Mayor of Chicago, lived here during his mayoralty). Both the gentrified and ungentrified areas are noted for absolutely beautiful residential architecture and tree-lined streets.

    Far Northwest Side 
Far Northwest Side: Usually conflated with either the North Side or Northwest Side, this area is a mix of working-class and upper-class communities, many of which are indistinguishable from the suburbs. The population of the wealthy communities are largely well-paid white collar workers who have to live in Chicago as part of their contracts, but would prefer to live in the suburbs. It also is home to O'Hare International Airport, one of the busiest international airports in the world, and a hub for American Airlines and United Airlines (the latter of which is headquartered in the Sears Tower). Notable neighborhoods include:

  • Jefferson Park: A working-class neighborhood largely inhabited by Poles and Mexicans. Buses, Metra trains and the Blue Line converge near the middle, so the neighborhood gets lots of through traffic.
    • Also home to a large number of police and firefighter households.
  • Sauganash: A neighborhood that's pretty much a suburb in everything but designation, it is home to most of the city workers mentioned above.
  • Norwood Park: A former resort, this middle- to upper-class community is best known for being the only Chicago neighborhood to favor Republicans in most elections.
  • O'Hare: A blanket term for a community created when Chicago annexed a bunch of land in order to consolidate its claim over the land occupied by O'Hare International Airport. Because the land was purchased by lots, its borders are very confusing, and the western edge (comprising the southern part of the airport) is in DuPage County. The non-airport parts of the O'Hare neighborhood are mostly made up of office towers, hotels and some '50s-era working- and middle-class housing.

Chicago's most famous mayor was Richard J. Daley, who spent 21 years on the job before dying. Known (among other things) as "The Man On Five" after the floor his office was on. The last of the big "bosses" in U.S. politics, he was allegedly responsible for John F. Kennedy's suspicious Illinois electoral victory in 1960note  and built one of the most theatrically corrupt political machines in American history. This machine still exists, though it's more bipartisan and less powerful than it used to be. He was quite good at his job, though prone to George W. Bush-style misspeaking and dogged by controversies like the violence surrounding the 1968 Democratic Convention. His son is Richard M. Daley, who remained in office for 22 years, surpassing his father in length of tenure and arguably having as much if not more clout. In 2010, he decided not to follow in his father's footsteps and try to die on the job, so he stepped down after his sixth term—leaving the reins to former White House Chief of Staff Rahm Emanuel. Emanuel took office on May 16, 2011; consensus being that while Daley is a Tough Act to Follow, if anyone could do it, it would be "Rahmbo." However some Chicago residents in recent years saw some of "The Rahm Father's" dealings such as his handling of incidents of police brutality, and his management of the city's public school system as infuriating. Emanuel recovered some of his support by 2017, and initially planned to run for a third term in 2019, but eventually chose not to run. His successor, Lori Lightfoot, was the city's first openly LGBT mayor. Her election also made Chicago the largest city in America with a female mayor. Lightfoot would lose reelection in 2023 to Brandon Johnson, who has been serving as Chicago's incumbent mayor since May 2023.

Harpo Studios is home of The Oprah Winfrey Show and conspicuous as one of the only local production firms; history and economics left Chicago stranded between the film companies on the West Coast and the television studios on the East Coast. While Essenay Studios was a pioneer during the Silent Era and featured some of the biggest stars of the time, most notably Charlie Chaplin, Chicago's highly variable weather convinced them and other filmmakers to move to the more agreeable climate of California. As a consequence, Chicago has been relatively unexposed in American fiction, especially when compared to the omnipresence of New York City and Los Angeles. What little got under the wire tended to be gritty crime dramas that were shot in Toronto. This was mitigated somewhat by the loyalty of Chicago-trained talents (like John Hughes, David Mamet, and legions of The Second City improv troupe alumni), who often come back after hitting the big time to make affectionate, gangster-free movies. Lately, a weakening dollar and tax breaks have lured more and more films to the area, leading to an increase in cultural prominence that coincided with the rise of adopted Chicagoan Barack Obama. Chicago was the last city in the country that has a national "superstation"; WGN America aired Chicago's news stories to a national audience in the overnight hours, formerly airing frequent broadcasts of the Cubs and White Sox (and the Bulls, to a lesser extent). In 2015, Tribune Media began the process of converting WGNA to a regular cable channel (including selling off broadcast rights to the Cubs just before they won the World Series), thus striking the final nail in the "superstation" concept in the US. (WGN is also infamous for, along with PBS station WTTW-11, being hijacked in 1987 by a mysterious figure wearing a Max Headroom mask; the perpetrator has never been caught and theories abound over their identity and why they did it.)

Music and radio, on the other hand, have flourished in Chicago. Chicago, thanks to its location on the main route between the Mississippi and the East Coast, and the fact that it was a major destination for Southern blacks migrating north in search of better lives, was the first city outside of the South to really get hit by the waves of jazz and blues, developing unique styles of both. Various rock and pop bands also hit early, and as for hip-hop…well…let's just say that Kanye is from Chicago (although he was born in Atlanta), and leave you to judge for yourself. On the other end of the musical spectrum, the Chicago Symphony Orchestra (organized for the 1893 World's Fair when the city fathers wanted to show they could be just as cultured as older cities back East) is now considered one of the finest in the world, winner of 62 Grammies, and productions at the Lyric Opera of Chicago attract top-name international singers. On the radio front, Chicago is home to the notable WBEZ-Chicago, which produces both This American Life and Wait, Wait, Don't Tell Me. Another Chicago station, WLUP ("The Loop", a rock station) was responsible (in part) for the original Disco Demolition Night, which had a lasting effect and helped form the Disco Sucks trope.

Chicago is also considered the birthplace of American Pinball; almost all of the major manufacturers from the 1930s through the 1970s were based in or near Chicago, including Bally, Williams Electronics, Chicago Coin, Gottlieb, and Stern Electronics. Even now, the world's biggest Pinball Expo is held annually in Chicago. An outgrowth of this was video game development, most (in)famously the Mortal Kombat franchise, whose lead developer, Nether Realm Studios (successor of Midway Games) is based in Chicago.

The city is also very particular about its pizza and hot dogs. Chicago is famous for its deep dish pizza, developed in the 40s (although it isn't known who exactly invented it). With its deep crust, it resembles a pie more then other kinds of pizzas. Unlike other pizzas, the ingredients are assembled "backwards", starting with the cheese as the first layer, then a meat layer, a vegetable layer, and then the sauce last. This is due to a longer baking time that would burn the toppings and cheese if it was assembled in the same way as other pizzas.

One thing most non-locals don't know is that deep-dish isn't the city's most popular pizza. That honor belongs to thin-crust pizza, popular not only in Chicago but also in much of the Midwest. The crust is noticeably crunchy, and it's cut into squares instead of wedges. The quicker preparation makes it Chicago's everyday pizza for casual gatherings and quick bites at the bar; deep-dish is more of an event, reserved to celebrate momentous occasions like graduations and engagements. Also of note is that while pepperoni is the most popular pizza topping in most of the US, Chicago's most popular topping is sausage (regardless of the crust type).

As for its hot dogs, the quintessential Chicago-style hot dog must have a poppy seed bun, an all beef frank, yellow mustard, chopped onions, bright green relish, a pickle spear, tomato slices, a hot pepper and celery salt. Some vendors in certain neighborhoods are also known to add raw cucumber slices, but they are not counted as absolutely needed. The one ingredient that must not be used is ketchup. If you ask for ketchup, be prepared to get accused of having the palate of a child and laughed at. If a hot dog place has ketchup at all, it will be made very clear that it is meant for the fries and the fries only.

Sports in Chicago are very passionate subjects, although their fans tend to have a well-deserved reputation for idealizing the sports instead of looking at them objectively.note  With The Stanley Cup in 2010, Chicago became the first city on the continent to win all four of its big major professional sports championships in a 25-year spannote . Its record was broken a year later by Boston when the Bruins' Stanley Cup win brought the span down to seven years. However if you include soccer in the mix, Chicago regains the title as the New England Revolution have never won an MLS Cup.

Because the city has loads and loads of teams, both at the major and semi-major level, we'll put them in their own folder.

    Chicago Sports Teams 
  • The Bulls led by Michael Jordan in The '90s are considered one of, if not the greatest, sporting dynasty of all time. After a few years ranging from OK to bad they enjoyed a resurgence with the drafting of area native Derrick Rose. Unfortunately for all involved, however, Rose was prone to injury and traded away in 2016. The team is once again trying to rebuild.
  • The Bears have remained popular, and it's hard to find anyone who doesn't remember Walter Payton or the team's victory in Super Bowl XX. Unfortunately, this has a habit of creating a fan base that doesn't really understand that winning a Super Bowl in 1985 doesn't lay out a blueprint for victory today.
  • Baseball loyalties are split between the National League Cubs on the North Side and American League White Sox on the South Side. Both teams suffered from legendarily long titles droughts until the Sox won the World Series in 2005note , while the Cubs made it to 108 years with nothing before finally breaking the streak in 2016. Each has periods of ups and downs, though most of the time neither team is really anything to write home about — for instance, in 2012 the Cubs were the second worst team in all of baseball, and while the Sox managed to finish the same season only a few games behind the American League Central-leading Detroit Tigers, that spoke more to the mediocrity of the AL Central that year rather than the particular quality of the Sox (or the Tigers for that matter). That said, the Fandom Rivalry tends to spark interest regardless of how they are actually playing.
    • An interesting wrinkle: the White Sox won the cross-town matchup in the 1906 World Series. However, the Cubs accomplished many firsts in their title runs of 1907 and 1908 (and another World Series run in 1910 that ended in defeat):
      • First Team to make three consecutive World Series (1906, 1907, 1908)
      • First team to make three World Series (1906, 1907, 1908)
      • First team to appear in four World Series (1906, 1907, 1908, 1910)
      • First Team to sweep a World Series (1907 over the Detroit Tigers)
      • First Team to win two World Series (1907, 1908— both over the Detroit Tigers)
      • First Team to win back-to-back World Series
      • First Team to play an extra-inning World Series game (a 1907 Game 1 12-inning tie against Detroit)
      • First Team to win an extra-inning World Series game (Game 4 in 10 innings for their own win in the 1910 series against the Athletics)
      • Longest World Series game winning streak (6 Games)
      • Most consecutive World Series games won (6 —- the last 4 in 1907, and took a 2-0 lead in 1908)
      • Longest championship drought in American sports, lasting an astonishing 108 years starting in 1908 and finally ending in 2016
    • An important tidbit: There is a silver lining to the Cubs' perpetual haplessness: everyone who isn't a Sox fan tends to love them, or at least doesn't hate them (the Cubs' in-league/in-division rivals, the St. Louis Cardinals, traditionally tend towards disdain, as the Cardinals have historically been one of the better teams in baseball, though the Cubs getting good again in 2015 seems to have (re)ignited some heated rivalries with the other teams in their division). They're the quintessential lovable losers, more than any team in American sports. While this is mostly due to the long drought, it's also a function of the Cubs fanbase: fanatical and rowdy, but also very fun to be around and nice to fans of opposing teams (except for Sox fans and to a lesser extent Cards fans). This is the main reason that Wrigleyville gets the aforementioned good reputation from visitors.
      • A good analogy for people who follow Association Football is the Tartan Army (the fans of the Scottish national team): Scotland have been hopeless for several decades, but its fans have been noted for being very warm, if ridiculously devoted and absurdly drunk (or is it the other way 'round?).
  • Last, but not least is the Blackhawks. Like the sport itself, the Hawks have classically played last fiddle to the more popular sports and their teams. The Hawks entered a severe Audience-Alienating Era in the late 1990s, mostly because of a penny-pinching ownernote  who was most well known for not letting Blackhawks games air on local television. However, management changes and hot draft picks made after the passing of said owner (who was loudly booed by nearly every Blackhawks fans in attendance when a moment of silence was performed to commemorate his death) allowed the team (now in the hands of his son) to win a Stanley Cup victory in 2010. This however proved to be a double edged sword as with success comes popularity, and many diehard fans began to be grumble about those new, young, ethnically diverse people who have the nerve to claim to be fans of equal value as they are, and how said interest in the Hawks has increased ticket prices. Despite early exits from the playoffs the next two years, the team remained relatively successful and popularity continued to grow. They were credited with a league record in 2011 playing 24 consecutive games without a regulation loss, that being half of the lockout-shortened 48-game schedule. They would go on to win their second President's Trophynote  in franchise history and take their second Stanley Cup in four years. Despite the 2011 NHL lockout alienating some fans, the team's popularity has only grown with a third Stanley Cup win (sixth in franchise history) in 2015. With 3 championships within 6 years the team has been said to be in a dynasty phase, and they are currently by a wide margin the city's biggest name in sports outside of the 2016 World Series Champion Cubs, even pushing the still-well-regarded Bulls out of the limelight, something that would have been unthinkable a few years earlier.

Outside of the big five teams, the city and surrounding suburbs are also home to numerous other pro sports clubs that have amassed solid, consistent followings.

  • The MLS Chicago Fire FC won a championship in their first season and have maintained popularity throughout ups and downs over the years. Their former stadium, SeatGeek Stadium (originally Toyota Park, in suburban Bridgeview), is one of the first major soccer-specific stadiums built in the U.S. In 2019, they were purchased by a new owner, who promptly brought them back to Soldier Field... only for the COVID-19 pandemic to put their "homecoming" on hold. Also, they share their name with the TV show. Fans of the soccer team are annoyed about that.
  • Allstate Arena (formerly Rosemont Horizonnote ) may as well be considered the world's greatest semi-pro arena. Built for DePaul University basketball, it was to be the permanent venue for the short-lived Chicago Cougars of the World Hockey Association, but the league and team went under before they could move innote . In 1994 the Wolves of the International Hockey Leaguenote  moved in, and the arena has since also become the home of the WNBA's Sky and formerly the Arena Football League's Rush.
    • The Wolves won two championships in their first 6 seasons which led to a large fan following as their success coincided with the Blackhawks' Audience-Alienating Era. After the IHL folded, the team joined the AHL, the top level of the NHL farm system where they won two more championships as affiliates of the Atlanta Thrashers. Their popularity dwindled as the perpetually-bad Thrashers began poaching their good players and then trading them away. Their decline continued with the resurgence of the Hawks. Plenty of fans are still there, but it's hard to fill a stadium three times the size of the average for the AHL, especially with a thriving NHL team in town. In 2011, with the Thrashers being bought and moved to Winnipeg, the Wolves aligned with the Hawks' Arch-Enemy Vancouver Canucks, alienating some fans and just making others feel awkward. The Canucks bought the Peoria Rivermen at the end of the 2010-2011 season, leaving the Wolves to affiliate with the St. Louis Blues,note  another of the Hawks' notable rivals. The consensus among fans with regard to the deal was mostly along the lines "well at least it's not Vancouver". In the 2017–18 season the Wolves became the affiliate team of the Vegas Golden Knights, with the Blues becoming an associate affiliate allowing both teams to utilize the team's roster for one year, after which the Blues found another AHL team.
    • Before finally winning their first WNBA title in 2021, the Sky didn't do much in terms of winning—they never made the playoffs until 2011—but are still as popular as you would expect any other WNBA team to be, and notably were founded without the affiliation of an NBA team.
    • The Rush were somewhat of an Ensemble Dark Horse from being consistently goodnote  and being co-owned by legendary Bears coach Mike Ditka. However, the team was disbanded after the AFL took over ownership in 2011.
    • More recently, Allstate Arena has lost two of its major tenants. DePaul moved its men's basketball team to Wintrust Arena, a newer and smaller venuenote  that opened in 2017 at the McCormick Place convention center on the Near South Side. The school also made the new arena a second home for its women's basketball team, though many of that team's games are still in DePaul's much smaller on-campus arena. The Sky joined the Blue Demons there in the 2018 season (keep in mind that the WNBA plays a summer season, during the traditional basketball offseason).
  • Women's soccer has the Chicago Red Stars, which were members of four different leagues in their first five years of play. Currently, they play in the National Women's Soccer League, which is the country's third attempt to establish a professional women's soccer league.note  The Red Stars stayed in Bridgeview after the Fire skedaddled back to Soldier Field.
  • Rounding out the list of semi-major teams in Chicago is the women's pro softball Bandits who won their first championship in 2009.
  • The metro area is also home to numerous minor league teams. The Kane County Cougars, in neighboring Kane County, were the only team in the region affiliated with a Major League Baseball team (besides the South Bend Cubs, but the jury is still out on whether or not South Bend is close enough to Chicago for it to be in the region) until MLB reorganized the minor leagues in 2021, leaving the Cougars out. They found a home in the independent American Association, already home to the Chicago Dogs (playing in Rosemont) and the Gary SouthShore RailCats. The independent Frontier League is home to the Windy City Thunderbolts in south suburban Crestwood, the Schaumburg Boomers, and Joliet Slammers. In basketball, the Windy City Bulls play in Hoffman Estates as the Bulls' G League team.

If you haven't figured it out by now, Chicago really loves its sports. The fact that it can support one (if not two) teams in each of the big four (five if you count MLS) leagues and also have teams in as many secondary leagues that still amass solid fanbases and financial stability is a testament to the city's love with any and all things sporting related.note 

Chicago also has a significant place in the recent history of professional wrestling. The Now Arena (formerly Sears Centre Arena), home to the aforementioned Windy City Bulls, hosted the wildly successful All In indy show, run by Cody Rhodes and The Young Bucks in 2018. The success of All In was the springboard for the creation of All Elite Wrestling a few months later. More recently, Chicago native CM Punk returned to wrestling in 2021 in his hometown, making his AEW debut at a special episode of Rampage held at United Center before his in-ring return at All Out at Now Arena.

Chicago is notable also for its street numbering system and for having its own flag. The four stars depict four major events in the city's historynote . The addition of a fifth star has long been proposed, with the most commonly-agreed-upon criterion being the Cubs winning the World Series— which at the time of the proposition hadn't happened since 1908. However, given that the Cubs finally won another World Series in 2016, time will tell whether or not that fifth star becomes a reality; the Chicago History Museum is currently holding a campaign to encourage residents to vote on such an addition, and mayor Lori Lightfoot suggested that the city's response to the COVID-19 Pandemic in 2020 could also be a good qualifying event.

See also Gangster Land, for the most enduring Chicago trope, and Down on the Farm, for the region surrounding the city.note  It is worth noting, however, that as the years go on, the area directly north of Chicago is a lot closer to Suburbia and Strip Malls than Down on the Farm, as the metropolitan areas of Milwaukee and Chicago continue to grow, causing bordering communities to continue to grow as well. In any other direction, however, this is true— with only smaller cities such as Elgin (to the west) and Rockford (to the northwest) breaking up a huge quantity of Down on the Farm interspersed with Everytown, America.

Chicago in fiction:

    open/close all folders 

    Anime and Manga 

    Comic Books 

    Film — Live-Action 

  • "Chicago", the memorable poem by Carl Sandburg. "Hog Butcher for the World, Tool Maker, Stacker of Wheat, Player with Railroads and the Nation's Freight Handler; Stormy, husky, brawling, City of the Big Shoulders..."
  • Complete World Knowledge double subverts Chicago. According to the first book in the series, Chicago is actually nothing but myth, along the lines of Brigadoon. During the End Times of 2012, however, as chronicled in the final part of the trilogy, Chicago rises up from the mud at last.
  • Crossing California
  • The Dispatcher
  • Divergent: Explores a post-apocalyptic Chicago. Notable in that, unlike in other young-adult dystopia, from start to finish, the series is set in Chicago and only Chicago; the closest the series has come to exploring other locations is when the characters reach O'Hare International Airport in the third book, which is partially located in DuPage County (Chicago is in Cook County) but is still owned by the Chicago Government. Veronica Roth wrote the series while attending Northwestern University.
  • The Dresden Files
  • Everworld — The setting opens in northern Chicago, where all the main characters are from, and after being pulled into the titular Everworld the narrative oscillates between the travails of the kids through Everworld and their periodic returns to everyday life in Chicago when they fall asleep or are otherwise made unconscious. In the last book it is heavily implied the kids have crossed over entirely into Everworld as the last two pages detail a February 18, 2001 Chicago news story detailing the mysterious disappearances of five local teens.
  • The Heroes of Olympus: Aeolus, the Keeper of the Winds, is based here. Although Riordan doesn't seem to realize that Chicago is called the "Windy City" because of blustering politicians, not the weather. It is windy, though. Especially in the winter, when it's also freezing cold. Also, perceptions are important in this series, so if people think that Chicago is literally windy, that's where the Wind will go.
  • Honor Harrington: the capital city of the Solarian League
  • The Jungle
  • Kasia revolves around a Fish out of Temporal Water princess from a fictional Eastern European kingdom who ends up here and has to learn to adapt to 21st-century life, set largely around the time the Cubs broke their title drought.
  • Native Son
  • Pet Sematary and its film adaptation feature Louis Creed moving with his family from his Chicago home to Maine to teach, though his wife and children later return to Chicago for Thanksgiving. He really should have stayed back home...
  • The Vampire Files
  • Steelheart is another YA book featuring a post-apocalyptic Chicago, transmuted into steel and governed by the titular supervillain.
  • Years of Grace tells the story of America from the 1890s to the 1920s, as told from the perspective of a protagonist who starts out as an upper-class Chicago teenager, and finishes a wife and mother in middle age. One of the sub-themes of the book is how the city grew and changed in the early 20th century. Jane is not too pleased when quiet residential Pine Street where she grew up becomes Michigan Avenue, one of the city's main thoroughfares. Near the end she is worried about her elderly mother, continuing to live in the old family home even as a skyscraper goes up that will put the whole house in shadow.

    Live-Action TV 

  • Trapped in the ClosetR. Kelly is from Chicago.
  • Of the members of Fall Out Boy most of them grew up in the suburbs surrounding Chicago, and many were part of the Chicago punk scene in the '90s, prior to forming their own band. Many songs from their first album, Take This To Your Grave, reference Chicago.
  • The members of The Academy Is... all grew up in Chicago. Their third (and final) album, Fast Times at Barrington High, is named after their high school in Barrington, Illinois.

    Newspaper Comics 
  • Although Dick Tracy has always insisted that Tracy's unnamed big city is not, itself, Chicago (for one thing, Tracy's sidekick Sam Catchem is described as being from Chicago), it is very clearly based on Chicago. The strip was conceived as a big Take That! against organized crime in The '30s, and Chicago was a huge hub of mob activity at the time, hence the connection.


    Tabletop Games 
  • Vampire: The Masquerade: Chicago and nearby Gary, Indiana were the very first settings detailed in the classic 1990's roleplaying game. Chicago became known as Vampire's "Signature City" after the release of Chicago By Night and a number of modules gave the city enormous detail within the context of the game.
  • The New World of Darkness has a sourcebook for using Chicago as a setting from the perspective of mortals, and describing the politics of Vampires, Werewolves, and Mages in the area.
  • Shadowrun turned Chicago into an insect-spirit-infested wasteland in Bug City.


    Video Games 


    Web Original 

    Western Animation 
  • Around the World with Willy Fog: Fog and his companions arrive in Chicago in the middle of a snowstorm which prevents them from continuing their journey by train. They set out to cross the Great Lakes in an ice boat, but their journey is interrupted when the cold proves too much for Tico.
  • Biker Mice from Mars
  • Exo Squad - renamed Phaeton City during the Neosapien occupation; home to La Résistance led by ex-Chicago cop Sean Napier
  • Nature Cat: Takes place in the metro area. The main animals have run past the river, as well as the Cloud Gate (the bean-shaped sculpture in Millennium Park).
  • The Simpsons: Mr. Burns took Homer to Chicago, which he refers to as "the Miami of Canada," in episode "He Loves to Fly and He D'oh's".

Famous and Notable Chicagoans:

"Rock over London! Rock on, Chicago! Chicago! The Windy City!"

Alternative Title(s): The Windy City