Chicago - TV Tropes

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

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, and is one of the very few structures to survive the 1871 fire.
• 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: 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. The strongest legacy of this is a large Asian community in the area centered on Argyle St (a sort of second Chinatown, but with more Southeast Asian people as well). 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 split off and became its own community area in 1980. 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, home of Northwestern University.)
• 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: 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. The World's Columbian Exposition in 1893 was hosted in this neighborhood. The Palace of Fine Arts is one of the few buildings built for the expo that remains today. The building now holds the expansive Museum of Science and Industry, which contains, among many other things, the World War II-era 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: 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: 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 massive 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, and it plays host to the lion's share of the community's truly gigantic Mexican Independence Day celebrations (which attract literally hundreds of thousands of people every year). However, 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 history^note , most notably the 1991 NHL All-Star Game^note .

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 'L' Ravenswood branch of what is now the Brown 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: 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.

• 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 2005^note , 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 owner^note  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 Trophy^note  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 Horizon^note ) 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 in^note . In 1994 the Wolves of the International Hockey League^note  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 good^note  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 venue^note  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. After Punk was fired amid backstage turmoil in 2023, he returned to WWE that November, making his first appearance for that promotion since 2014 at Survivor Series: WarGames at Allstate Arena (though he didn't wrestle at that event).

• 91 Days
• Baccano!
• Gunsmith Cats
• Riding Bean
• The Cat Returns
• The Ancient Magus' Bride

• Johnny Dynamite battled the underworld in Chicago.
• The Savage Dragon
• Tintin in America

• 8-Bit Christmas
• Above the Law (1988)
• Adventures in Babysitting
• American Beauty — but this is only noticeable by looking at the area codes seen for various phone numbers in the film (847, which is the northern suburbs, and 312, which is Chicago's most well-known area code)
• Baby's Day Out
• Backdraft
• Bad Teacher
• Barbershop
• Beginning of the End
• The Blues Brothers wouldn't have worked in any other city.
• The Breakfast Club takes place in the fictional Shermer, Illinois, which is a Chicago suburb. Subsequent John Hughes films such as Weird Science are also set in Shermer.
• The Break-Up
• Bullitt — while the main part of the film is set in San Francisco, the opening credits scene takes place in Chicago. The very first thing we see in the film is a shot of the now-demolished Sun-Times Building.
• Calamity Jane: The title character makes a trip to the Windy City.
• Candyman: Filmed on location at the real life Cabrini-Green housing project on Chicago's north side.
• Casino - although it's only identified as "Back Home", some of the film does take place in the Windy City for the scenes involving Nicky Santoro and the Chicago Outfit. Additionally, other characters make references to the city.
• Child's Play - The first two films of the franchise are set in Chicago, and the original was filmed there to boot. The absurdly-spacious apartment Karen and Andy occupy in the first film was actually filmed in the Brewster Apartments, an actual historic apartment building located in Lakeview.
• Children of the Corn III: Urban Harvest
• Code of Silence
• The Color of Money
• Cooley High
• The Dark Knight Trilogy: The first two films in the trilogy use Chicago to represent Gotham City.
• The Dilemma
• The beginning of Down in the Delta is set in Chicago (which is played by Toronto).
• Eagle Eye
• Ferris Bueller's Day Off is generally considered a classic Chicago film, as it essentially provides a tour of the city's most recognizable landmarks as part of its plot.
• The Fugitive - 1993 film and 2000 TV series.
• The Fury - The novel was set in New York, but the setting changed when it was decided to film in Chicago.
• The Grudge: The second and third films are set partially and entirely, respectively, in Chicago.
• Hardball
• High Fidelity
• Home Alone: The first movie is mostly set in Winnetka, a wealthy north Chicago suburb, but the family (sans Kevin) does fly out of O'Hare. The sequel starts in the same place before heading to the Big Applesauce.
• Hoop Dreams - documentary about two high-school basketball players from the slums.
• In Old Chicago is a heavily fictionalized movie about the 1871 fire.
• I Want Someone to Eat Cheese With is set and filmed in Chicago including several shots of Wrigley Field and Millennium Park and starring alumna of Second City.
• I, Robot
• Independence Day - Chicago is mentioned to have been destroyed by the aliens in the second wave, along with Atlanta and Philadelphia.
• Jupiter Ascending spends some time traveling Earth—and beyond—but the protagonist lives and works in Chicago.
• Let's Do It Again
• Man of Steel used Chicago as a fill-in for Metropolis (for instance, Supes kills Zod in the Great Hall of Chicago Union Station) and used the nearby town of Plano to represent Smallville.
• Max Keeble's Big Move - Kind of; the setting itself is actually in either California or Washington state, but a large portion of the plot involves the possibility of moving to Chicago, which was also mistaken for Detroit by Robe, although Max does identify it by the correct nickname of the Windy City in the movie.
• Mean Girls is set in Evanston, an affluent Chicago suburb that's most notable for hosting the main campus of Northwestern University.^note 
• Monster a-Go Go
• The Murder of Fred Hampton is a documentary about Hampton the Black Panther leader and how he was killed when the Chicago police raided his apartment on December 4, 1969.
• My Big Fat Greek Wedding
• National Lampoon's Vacation series - The Griswalds live in Chicago.
• The Negotiator
• Never Been Kissed
• Planes, Trains and Automobiles — The whole film is about Steve Martin's character trying to get home to Chicago for Thanksgiving, with John Candy as his hapless and unwanted traveling companion.
• Public Enemies
• The Rebel Set — A 1959 movie about an armored car robbery planned during a four hour train stop in Chicago. As seen on Mystery Science Theater 3000.
• Red Heat
• Return to Me
• Road to Perdition
• Richie Rich
• Risky Business — featuring a sex scene on an L train!
• Running Scared (1986) starring Billy Crystal and Gregory Hines—featuring a car chase on an L train track!
• Rookie of the Year
• The Santa Clause
• Some Like It Hot — The film begins in 1929 Chicago, with its plot driven by the lead characters witnessing the St. Valentine's Day Massacre and having to take it on the lam.
• Source Code is set in Chicago, though most of it was shot in California and Montreal, to go with a huge amount of Just Train Wrong.
• The Sting
• Stranger Than Fiction
• Tommy Boy - Tommy and Richard face Ray Zalinsky at his business headquarters in Chicago.
• The Time Traveler's Wife (2009)
• Transformers: Dark of the Moon
• Uncle Buck
• The Untouchables (1987)
• Uptown Saturday Night
• Wanted - at least, the movie, anyway.
• Watch It
• Wayne's World was set and partially filmed in Aurora, a Chicagoland suburb.
• What Women Want
• Wicker Park
• Wildcats (1986)

• "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.

• According to Jim
• Against the Wall: set in Chicago, filmed in Toronto.
• Anything But Love
• APB
• The Bear (2022)
• The Beast 2009: actually filmed in Chicago
• Betrayal
• Boardwalk Empire: While the main action is set in Atlantic City, Al Capone is a recurring character through the series, and several other characters have arcs that take them to Chicago at some point.
• The Bob Newhart Show
• Boss: TV Series starring Kelsey Grammer as the secretly dying and completely corrupt mayor of Chicago.
• The Chicago Code
• Chicago Hope — Howdy-doody again.
  • Dueling Shows with ER, since both focused on Chicago hospitals and debuted the same fall.
• Chicago Sons
• Chicago Story — Need I say it?
• A CSI: NY story is partly set in Chicago, particularly the Tribune Tower. The Tower has bits of other famous world buildings in the walls.
• Due South
• Early Edition
• Elseworlds: Chicago is used to portray Gotham City.
• ER: Many token outdoor shots and anything involving the "L" were indeed filmed in Chicago. But if you watch carefully, there are numerous scenes of people walking outside, bundled up against the harsh Chicago winter — but you can't see their breath.
• Family Matters
• Fargo: The fourth season uses Chicago as a stand-in for 1950s Kansas City.
• Father Dowling Mysteries: Set in Chicago, although it was actually filmed in Denver for the first season and in Los Angeles thereafter.
• The Forgotten
• Friends with Benefits — the NBC TV show, not the movie. Set in Chicago, filmed in New York City.
• Good Times : The Evans family lives in the projects on the South Side.
• The Good Wife was set in Chicago, but filmed in New York City.
• Happy Endings
• Hill Street Blues: While the city is technically unnamed on the show, the opening credits utilize Chicago locations.
• I Didn't Do It: While the first season was set in Evanston (which is immediately adjacent to Chicago's northern border), the second season essentially retcon this, setting the show in Chicago proper.
• Kenan & Kel
• Kolchak: The Night Stalker
• The League
• Lois & Clark: Though the show is set in the fictional city Metropolis, Chicago is used in many shots, and the Chicago flag is visible in a few scenes.
• The Loop
• Married... with Children
• Mike & Molly
• The Mob Doctor
• My Boys — the main character is a beat writer for the Cubs.
• One Chicago
  • Chicago Fire
  • Chicago P.D.
  • Chicago Med
  • Chicago Justice
• Pearson
• Perception (2012)
• Perfect Strangers
• Prison Break features Chicago extensively in its first season, as the Fox River prison is located in the nearby Joliet, Illinois, and all of the main characters live in Chicago.
• Punky Brewster
• The Real O'Neals
• Shake It Up
• Shameless (US)
• Siskel & Ebert — The opening credits showed the two movie critics from rival Chicago newspapers individually walking through the streets of their hometown and meeting in front of a movie theater.
• Stargate SG-1 — Jack O'Neill is from Chicago, referenced in this exchange with an alien (sorta)

  Fro'tak: I am Fro'tak of the High Cliffs.

  O'Neill: Jack, of The Windy City.

  • Of course, O'Neill is also from Minnesota; he seems to have grown up there (hence the accent).
• Still Standing
• The Steve Harvey Show
• Turks
• Two of a Kind, which even included an episode where, in a Shout-Out to Bueller, the father takes in a game at Wrigley Field.
• The Untouchables
• Webster
• Whitney
• The Young Indiana Jones Chronicles — As mentioned in Raiders of the Lost Ark Indy goes to college at the University of Chicago (and ends up teaching archaeology at his alma mater). In the episode "Mystery of the Blues" set in 1920, Young Indy is a college student working as a waiter at a jazz club, and his roommate is Eliot Ness.
• The rebuilt New Chicago is Earth's capital city in Buck Rogers in the 25th Century, and most of the activity we ever see on Earth is set there.

• Trapped in the Closet — R. 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.

• 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.

• Bone Busters depicts the city under attack from an army of animated skeletons.

• 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.

• Chicago
  • The movie, however, was filmed mostly in Toronto, to the annoyance of many Chicago viewers. When asked what he thought of the movie Chicago, Mayor Daley replied, "I would have liked it better if it had been filmed in Chicago!" To a Toronto viewer who didn't see it as a big deal, Chicago film critic Roger Ebert retorted, "If a musical named 'O Canada' were currently being filmed in Chicago, how would that make you feel?"
• Clybourne Park: Pulitzer Prize winning drama by Bruce Norris builds on Lorraine Hansberry’s Chicago of A Raisin in the Sun.
• The Front Page
• Glengarry Glen Ross
• Pal Joey: "There's a great big town on a great big lake..." (The film version, however, was reset in San Francisco.)
• Sexual Perversity in Chicago, a David Mamet play filmed as About Last Night.
• Show Boat's second act opens at the 1893 World's Fair.

• The Festive Fury update of Asphalt Legends Unite marks the debut of the Chicago track.
• A large portion of Fallout Tactics: Brotherhood of Steel takes place in and around the ruins of Chicago. It is also mentioned, but never seen, in the Lonesome Road DLC for Fallout: New Vegas where it is revealed that the Midwest Brotherhood were eventually pushed out by The Enclave and Chicago is currently their last remaining stronghold following their crushing defeats in the California Gulf and the District of Columbia.
• Magical Warrior Diamond Heart is all but explicitly stated to take place in Chicago. The cast mention living in Illinois in "one of the bigger cities in the country" and at one point can visit a museum featuring the dinosaur, SUE.
• Michael Jordan: Chaos in the Windy City
• Michigan: Report From Hell, despite what the title would have you believe.^note 
• Midtown Madness
• Mortal Kombat has had a few stages set in what's implied, but never outright stated, to be Chicago; Cole Young, the protagonist of the 2021 MK film, is stated to be from the south side (presumably also being home to the gym he works at), while Sonya's home is in the nearby suburb of Gary, Indiana. This falls under Creator Provincialism, as developer Midway Games, and successor Nether Realm Studios, are/were based in the city (for the former being heavily linked to Williams Electronics beginning in the 1980s, leading to frequent references between Midway's video games and the Williams/Bally pinball machines of the era).
• Watch_Dogs takes place in a heavily stylized Chicago, mostly on the South, West, and Lower West sides. Video Game Geography is at play; Pawnee, which is almost 200 miles southwest of Chicago in real life, is treated as a nearby suburb and plays The Mountains of Illinois trope literally.
• Deus Ex: Invisible War: The intro is set here. It's a Doomed Hometown for the protagonist though, as it is leveled by a nanite bomb.
• Need for Speed Unbound is set in Lakeshore City, a stand-in for Chicago that also includes the surrounding rural areas in the state borders with Iowa and Wisconsin.

• El Goonish Shive's Moperville is based on Naperville, IL in the outer suburbs.
• Multiplex — Word of God has that it's set in "Skokiston"/"Skevanston" (a mix of Evanston and Skokie, two northern Chicago suburbs).
• Paradigm Shift

• Channel Awesome — Doug Walker and the site's senior staff all live in suburban Chicagoland (mostly in Naperville).

• 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".

• Steve Albini
• Mustafa Ali
• Gillian Anderson
• Patricia Arquette
• Ed Asner: Born in Missouri, raised in Chicago.
• Sharif Atkins: Born in Pennsylvania, raised in Chicago.
• Reiko Aylesworth
• Adam Baldwin
• Ike Barinholtz
• Jennifer Beals
• Andy Bean
• James Belushi
• John Belushi
• Chloe Bennet
• Jack Benny
• Emily Bergl
• Michael Ian Black
• Scarlett Bordeaux
• Lara Flynn Boyle
• Andre Braugher
• Ray Bradbury
• Broken Hope
• Hannibal Buress
• Edgar Rice Burroughs
• Colt Cabana
• L. Scott Caldwell
• Sarah Wayne Callies (born in La Grange; later moved to and raised in Hawai'i)
• Al Capone: Yes, he was born in Brooklyn, but he didn't make a name for himself until he came to Chicago.
• Terrence C. Carson
• Dan Castellaneta
• Raymond Chandler
• Bailey Chase
• Chicago, of course
• Anna Chlumsky
• Hillary Rodham Clinton
• CM Punk
• Common
• Lana Condor
• Michael Crichton
• Piper Curda (born in Florida and raised in Chicago)
• Ann Cusack
• Joan Cusack
• John Cusack
• Bruce Dern
• Bo Diddley
• Walt Disney (born and spent his early childhood in Chicago)
• Brian Doyle-Murray
• Michael Clarke Duncan
• Kevin and Nora Dunn
• Earth, Wind & Fire
• Roger Ebert
• Gregg Edelman
• Fall Out Boy
• Dennis Farina
• Chris Farley
• Meagen Fay
• Neil Flynn
• Harrison Ford
• Bob Fosse
• Dennis Franz
• Cassidy Freeman
• Crispin Freeman
• Zach Gilford
• Bruce Glover
• Edward Gorey
• Kathy Griffin
• Michael Gross
• Kathryn Hahn: Born in Westchester, but raised in Cleveland Heights.
• Irma P. Hall
• Daryl Hannah
• Laura Harrier
• Wood Harris
• Sean Hayes
• Bobby Heenan
• Ernest Hemingway
• Isabella Hofmann
• Terrence Howard
• John Hughes: Born and raised in Michigan, but moved to Chicago at age 12.
• Jennifer Hudson
• Bonnie Hunt
• Jason Jordan
• Kalisto
• R. Kelly
• Echo Kellum
• Karlie Kloss
• Amy Landecker
• John Landis
• Krystal LaPorte
• Harry Lennix
• Jane Lynch
• Bernie Mac
• Tress MacNeille
• Michael Madsen
• Virginia Madsen
• David Mamet
• Joe Mantegna
• Ray Manzarek
• Brit Marling
• Curtis Mayfield
• Chi McBride
• Jenny McCarthy
• Jon McClenahan
• Frances McDormand
• Erica Mendez
• Alex Meneses
• Kel Mitchell
• Jennifer Morrison
• John Mulaney
• Martin Mull
• Bill Murray
• Bob Newhart
• Marisol Nichols
• Nichelle Nichols
• Barack Obama: Born and raised in Hawaii, but moved to Chicago with his wife Michelle, where he served as state senator, before being elected to the US Senate, then finally elected the 44th President of the United States in 2008.
• Oceano
• Nick Offerman
• OK Go
• David Otunga
• Mandy Patinkin
• Michael Peña
• Jeff Perry
• Zoe Perry
• Jeremy Piven
• Danny Pudi
• Harold Ramis
• John C. Reilly
• Rob Renzetti
• Shonda Rhimes
• Lauren Ridloff
• Craig Robinson
• Freddy Rodriguez
• Gina Rodriguez
• Michael Rooker: Born in Alabama, raised in Chicago.
• Veronica Roth: Born in New York, lives in Chicago
• Pat Sajak
• Kiele Sanchez
• Carl Sandburg
• Jessy Schram (born in Skokie, raised in Buffalo Grove)
• Stefanie Scott
• Amy Sedaris (born in Upstate New York, raised in North Carolina, but made her professional name in Chicago)
• David Sedaris (born in Upstate New York, raised in North Carolina, but went to college in Chicago and started his career there)
• Allan Sherman
• Sherri Shepherd
• Kiernan Shipka
• Nina Siemaszko
• Shel Silverstein
• Gary Sinise
• Gene Siskel
• Jeremy Sisto: Born in California, raised in Chicago.
• The Smashing Pumpkins
• Patti Smith
• Dino Stamatopoulos
• Styx
• Mr. T
• Allison Tolman
• Lauren Tom
• Robin Tunney
• Vince Vaughn
• Izabela Vidovic
• Doug Walker
• Gabrielle Walsh
• Matt Walsh
• Sam Wanamaker
• Raquel Welch
• Kanye West
• Wilco
• Robin Williams
• Wesley Willis
• Oprah Winfrey
• Barbara Alyn Woods
• Billy Zane
• Robert Zemeckis