Ferris Bueller spent a famous day off there, taking in an art gallery, a colourful street parade and a baseball game at Wrigley Field. Heath Ledger staged a bank robbery there as The Joker in The Dark Knight. And it's the city with America's largest film studio outside Hollywood, where the hit music industry TV series Empire is filmed.
When you think movie and television cities in the US, your first thought is Los Angeles and New York. But Chicago also has a vibrant history dating back more than 100 years, when 'Bronco Billy' Anderson shot silent westerns on the banks of the river.
Chicago can pass for Gotham City in the Batman movies and Metropolis in the Superman movies.
Charlie Chaplin also filmed in the Windy City, His New Job, but that's ancient history compared to all the well known movies that were shot at least partly there in the 1980s and '90s.
The list includes Home Alone, The Colour of Money, Risky Business, The Untouchables, Planes, Trains and Automobiles, Goodfellas, Top Gun, When Harry Met Sally, The Blues Brothers, Backdraft, About Last Night, Sixteen Candles, The Breakfast Club, Mission: Impossible, Wayne's World and The Fugitive.
More recently, the city has hosted scenes for Batman Begins, The Dark Knight, Oceans Eleven and Twelve, High Fidelity, Divergent, Insurgent, Man of Steel, Bridesmaids, the last two Transformer movies and the new Batman v Superman: Dawn of Justice.
In 2011, the company behind Toronto's Cinespace studios bought the former Ryerson steel plan and converted it into soundstages at a cost of $112 million. Alexander Pissios, the colourful Greek-American chief executive of Cinespace Chicago Film Studios says the facility covers more than 20 hectares.
"It's a pretty impressive piece of property, about 10 minutes from downtown Chicago. And slowly but surely, we took these big buildings that unfortunately the company needed to get rid of, and we transformed them into 20 stages."
Surrounded by Blackhawks ice hockey memorabilia and photos with stars, Pissios says the studio has three Dick Wolf TV shows, plus Empire, filming and plans to add more soundstages.
"It's in the middle of the country," he says. "It's a blue collar, hard-working city with great locations. That's why shows like to come here. We have great architecture. We have four seasons, which is nice. We have beautiful Lake Michigan.
"And you go an hour north from here, you look like you're in Kansas in the country. When they shot the last Superman, they used that part for Kansas. You go south, you've got the Indiana dunes, which is all sand. It looks like a desert."
With its striking architecture, Chicago can pass for Gotham City in the Batman movies and Metropolis in the Superman movies.
Pissios wants to build a backlot with tours for tourists next year.
"I'm in the works with the city now to fence this 52 acres," he says. "Then I'm going to take the facades of the buildings and make one New York, one Chinatown, one mainstream USA and one London. Then shows can use them for filming and people can take tours."
Ironically, the Oscar-winning musical Chicago didn't actually shoot in Chicago – chalk that up to Toronto. And even though some famous locations have been demolished - including the old hospital where Dr Richard Kimble looked for clues to his wife's killer in The Fugitive – movie fans don't have to wait for that studio tour.
Here's a guide to Cinematic Chicago.
NORTH BY NORTHWEST (1959)
After surviving a cropduster attack in Hitchcock's classic thriller, a suspicious Roger O. Thornhill (Cary Grant) meets up with Eva Kendall (Eva Marie Saint), believing she has been involved in the attempt on his life. The location is the Ambassador East Hotel, which is now the Public Chicago (1301 North State Parkway).
THE STING (1973)
While the best picture Oscar-winning crime caper is set in Chicago, it was mostly shot in Los Angeles. But one memorable scene used the LaSalle Street Station (414 South LaSalle Street). Getting off a train, crime boss Doyle Lonnegan (Robert Shaw) is met by Johnny Hooker (Robert Redford), who feigns interest in joining his gang. Inside the station, Henry Gondorff (Paul Newman) watches approvingly. The sting is on. Since an ungrade in 1981, the exterior seen in the movie no longer exists, but the historic station is still there.
THE BLUES BROTHERS (1980)
Some of the key locations from the classic comedy have been demolished, including Nate's Deli (807 West Maxwell Street), which was the Soul Food Cafe, where Aretha Franklin sang Think. But you can still see the locations from the famous police chase scene through the lower tier road system that ends with a spectacular pile-up (it starts on Lower Wacker Drive and ends at the corner of Lake and LaSalle streets). And the finale, as Jake and Elwood hand over the cash to pay the orphanage's taxes, takes place at Daley Plaza (50 West Washington Street) and City Hall (121 North LaSalle Street).
THE HUNTER (1980)
A little-known thriller that is notable for two things: it was Steve McQueen's final movie and it involved a spectacular stunt at one of the city's most colourful buildings – the corncob-like Marina Towers (300 North State Street). As McQueen's bounty hunter chases his prey, a car plunges off the building 16 storeys into the Chicago River.
FERRIS BUELLER'S DAY OFF (1986)
The quintessential love letter to Chicago sees Ferris (Matthew Broderick), girlfriend Sloan (Mia Sara) and best pal Cameron (Alan Ruck) enjoy the city's attractions during a day off school. They watch the baseball at Wrigley Field (1060 West Addison Street) and lean against the glass to look over the streets atop the Sears Tower, now the Willis Tower (233 South Wacker Drive).
Ferris sings on a float during the Von Steuben Day Parade (held annually in Dearborn Street), while Sloan and Cameron walk past Alexander Calder's sculpture Flamingo (Federal Plaza, 50 West Adams Street).
When the three friends head to the Art Institute of Chicago (111 South Michigan Avenue), they take in many of director John Hughes' favourite artworks. You can pick up a flyer at the institute for a mini-tour that includes Edward Kemey's lion sculptures guarding the front steps, Rodin's Portrait of Balzac, Jackson Pollock's Greyed Rainbow, Chagall's American Windows, where Ferris and Sloan share a kiss, and Seurat's A Sunday On La Grande Jatte, which mesmerises poor struggling Cameron.
RISKY BUSINESS (1983)
In the comedy that made Tom Cruise a star – everyone remembers the underwear dance – there is a memorable scene at the Drake Hotel (140 East Walton Place). Fresh-faced Chicago student Joel (Cruise) and best friend Miles (Curtis Armstrong) go looking for call girl Lana (Rebecca De Mornay). They wait awkwardly in the Palm Court before they catch up with her, which leads to a tense scene in the street outside.
THE UNTOUCHABLES (1987)
Gangster Al Capone (Robert De Niro) signals just how vicious he can be after an elegant black-tie dinner in Brian De Palma's crime thriller. During what seems like a pep talk to his guests, he beats a man to death with a baseball bat. The scene was shot at the elegant Blackstone Hotel, now the Renaissance Blackstone Hotel (636 South Michigan Avenue).
To recreate 1920s Chicago, De Palma also used exteriors of some of the city's most famous buildings, including the Rookery Building (209 South LaSalle Street) and Chicago Board of Trade Building (141 West Jackson Boulevard). For Capone's main headquarters in the long-gone Lexicon hotel, one of the locations was the upper lobby of the Chicago Theatre (175 North State Street).
HOME ALONE (1990)
When the McCallister family heads to Paris in Chris Columbus' family comedy, they set off from Chicago O'Hare International Airport. It also doubles as Paris Orly Airport after they realise that Kevin (Macaulay Culkin) has been left behind. And the McCallister family house, where Kevin is home alone, is in the northern suburb of Winnetka (671 Lincoln Avenue).
MY BEST FRIEND'S WEDDING (1997)
Muriel's Wedding director P. J. Hogan went to the US to shoot this romantic comedy with Julia Roberts, Cameron Diaz and Dermot Mulroney. The Hilton Chicago (720 South Michigan Avenue) features as Diaz's Kimmy confesses her insecurities about competing with Roberts' Jules. The hotel was also used for Home Alone 2, The Fugitive, Road To Perdition, Little Fockers and the rooftop helipad was used regularly for the TV series E.R.
THE DARK KNIGHT (2008)
The spectacular bank robbery staged by Heath Ledger's Joker takes place at the Old Chicago Main Post Office (433 West Van Buren Street), an historic building with 24 hectares of floor space that has been unused since the late '90s. (In Transformers: Dark of the Moon, Michael Bay used it as the department housing government autobots.) And just as in The Blues Brothers, the road system on Lower Wacker Drive was used for a spectacular scene as the Joker pursues a SWAT team convoy.
BATMAN V SUPERMAN: DAWN OF JUSTICE (2016)
While it was largely filmed in Detroit, Ben Affleck was spotted shooting a scene at Chicago's Marine Safety Station (250 North Breakwater Access), where the river meets Lake Michigan. Director Zack Snyder also turned the Aragon Ballroom (1106 West Lawrence Avenue) into a movie theatre playing The Mark of Zorro, apparently for a fateful visit for young Bruce Wayne and his parents. Playing Superman, Henry Cavill was hoisted over Clark Street for a scene that has him meeting Lois Lane (Amy Adams).
Qantas flies to Los Angeles (twice a day) and Dallas (six days a week) for American Airlines connections to Chicago.
The Hyatt Regency is a big four-star convention-style hotel with more than 2000 rooms in the downtown area overlooking the river.
Garry Maddox travelled at his own expense.