Chicago’s Greatest Hits | A rundown of the five best, must-see films set in Chicago: The Sting, The Blues Brothers, Ferris Bueller’s Day Off, The Untouchables, and High Fidelity.

Chicago is, without a doubt, one of the world’s legendary cities. It’s no wonder that so many iconic films have been set in the picturesque Windy City among its soaring skyscrapers, stunning parks, ornate train stations, and winding waterways. Here are just five of those movies and their most memorable Chicago-inspired scenes, which are beloved by fans around the globe.

1.) The Sting (1973) – Named Best Picture at the 1974 Academy Awards and set in 1930s Chicago, The Sting tells the story of conmen Johnny Hooker (Robert Redford) and Henry Gondorff (Paul Newman), who joined forces to seek revenge on notorious gangster Doyle Lonnegan (Robert Shaw). The two stage an elaborate con operation, but snafus along the way force them to take on the ruthless crime boss responsible for the death of their friend, Luther. While featured landmarks include Chicago Union Station, LaSalle Street Station, Penn Central Freight Yards, and the historic Central Station (which was demolished the following year), film buffs know the scenes that supposedly show the Chicago El were actually shot on the Universal Studios back lot in Los Angeles.

2.) The Blues Brothers (1980) – The Joliet Correctional Center, located about 40 miles outside Chicago, sets one of the very first scenes in this 1980s cult classic. Starring Saturday Night Live legends Dan Aykroyd and John Belushi, The Blues Brothers tells the story of brothers Jake (Belushi) and Elwood (Aykroyd) Blues. After his release from prison, Jake reunites with Elwood to play gigs to raise $5,000 to save the orphanage where the two grew up. After antagonizing the Chicago police, the brothers end up in a race against authorities and a deadline to deliver the money. Weaving through the city in their Bluesmobile, Jake and Elwood lead the police in a high-speed chase past numerous Chicago locations including Wrigley Field, the Cook County office building on Clark Street, and Daley Plaza with its 160-ton steel Picasso sculpture, a centerpiece of Chicago since its installation in 1967.

3.) Ferris Bueller’s Day Off (1986) – High school senior Ferris Bueller (Matthew Broderick) is the king of playing hooky. In an effort to cultivate the ultimate class-cutting finale before graduation, Bueller takes a “borrowed” Ferrari on a joyride through Chicago, cruising down Lake Shore Drive and visiting famous spots like Grant Park and the former Sears Tower. Principal Rooney (Jeffrey Jones) nearly catches Bueller after the high schooler appears on television enjoying a hot dog at Wrigley Field, but the truant student and his friends quickly sneak into the Art Institute of Chicago with a group of schoolchildren. It’s here that Bueller’s best friend, Cameron Frye (Alan Ruck) looks deeply into the Georges Seurat masterpiece, “A Sunday Afternoon on the Island of La Grande Jatte.” Written in just one a week, Ferris Bueller’s Day Off was called by director John Hughes a “love letter” to his adopted hometown of Chicago.

4.) The Untouchables (1987) – Set in prohibition-era Chicago, The Untouchables follows Agent Eliot Ness (Kevin Costner) as he strives to take down infamous bootlegger and mob boss Al Capone (Robert De Niro). After several failed attempts, Ness recruits a group of powerful lawmen, public officials, and police officers to aid him in his mission. One of the film’s most thrilling and suspenseful scenes culminates in a shootout between Ness, his partner George Stone (Andy Garcia), and mob accountant Walter Payne (Jack Kehoe) downtown in Chicago Union Station. A nearly five-minute build-up, tracked by the station’s famous clock, explodes in a rapid-fire shootout between the cops and Capone’s henchmen, who seem to appear out of the woodwork as chaos erupts.

5.) High Fidelity (2000) – The gentrified, mid-’90s version of Chicago’s Wicker Park neighborhood sets the tone for this music-infused tale of failed relationships, struggling record stores, and a protagonist suffering from Peter Pan syndrome. After Rob Gordon (John Cusack) is left by his long-time girlfriend (Iben Hjejle), he revisits his past lovers in what turns into a series of adventures in Chicago’s musical underground. Showcased venues include the now-defunct Lounge Ax and The Green Mill, a historic jazz club still open today. Gordon’s co-worker Barry (Jack Black) steals the show at Double Door, a bar freshly opened at the time of filming, when he performs Marvin Gaye’s Let’s Get It On with his band Barry Jive and the Uptown Five.