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Booking Chicago

To book Chicago or another Adult Contemporary musician for your private party, corporate event, fundraiser or other function, please fill out our Artist Request Form to quickly connect with one of our Booking Agents.

The staff of Headline Booking Group will work with you to produce a memorable event. Get started now by filling out our no-obligation Artist Request Form and we will work with you to book Chicago or another Adult Contemporary artist for your event.




Chicago continues to entertain audiences, both young and old. Their record sales top the 1 million mark, and include 21 Top 10 singles, five consecutive No. 1 albums, five No. 1 singles, 13 platinum albums and five gold singles. Of their 30 albums, 25 have been certified platinum. Chicago is also the first American band to chart Top 40 albums in five different decades.


The ambitious double-record, Chicago Transit Authority, hit record store shelves in 1969. The album became a college radio darling, and in May of 1969, it peaked at No. 17 on the Billboard charts. Shortly after the release, the band shortened its name to Chicago. After their first release, Chicago began the unique tradition of naming its records with Roman numerals, echoing the practice of classical composers who often organized their works this way. In the rock world, this is forever identified with Chicago.

Chicago II (1970), another two-record set, contained their first two Top 10 hits: ‘Make Me Smile’ and ’25, or 6 to 4.’ Their debut album held two more belated hits and also two of the band’s most requested songs, ‘Does Anybody Really Know What Time It Is?’ and ‘Beginnings,’ both written and sung by Robert Lamm. A third double album, Chicago III (1971) solidified their success.

In the fall of 1971, 18-year olds were finally given the right to vote. The band met with Ralph Nader, Senator William Fulbright, and politician Philip M. Stern to help determine ways to boost voter registration. The band registered voters at their concerts, and included voter info in their four-disc boxed set, Chicago At Carnegie Hall (1971). The next year, Chicago V (1972) topped the charts for nine weeks and spawned the gold single, ‘Saturday In The Park.’
Chicago VI was released in 1973 and stayed at No. 1 for five weeks. The album contained the hits ‘Feelin’ Stronger Every Day,’ and ‘Just You ‘N Me,’ the latter of which was a No. 1 hit and a gold single.

Chicago VII (1974) was yet another No. 1 LP for Chicago. The album included the hit single ‘Wishing You Were Here,’ which featured musical icons The Beach Boys.

Chicago VIII (1975) had the group’s fourth straight chart topper, the nostalgic hit ‘Old Days.’ Their next album, Chicago IX: Chicago’s Greatest Hits (1975) eventually sold five million copies. But it was Chicago X (1976), the recipient of three Grammy Awards, that featured the band’s biggest worldwide No. 1 hit of the 1970s: ‘If You Leave Me Now.’ The lovely ballad catapulted Chicago into the highest levels of popular success. Another ballad, ‘Baby, What A Big Surprise,’ was the major hit off Chicago XI (1977). In 1977, the band was awarded for their success with the ‘Favorite Rock Group’ title at the American Music Awards.

In early 1978, tragedy struck when guitarist Terry Kath was killed in a shooting accident. Devastated by the loss of their friend, the band nearly broke up, but eventually resolved to continue. Later that year, the band released Hot Streets (1978), which became another million-seller. Subsequent releases, Chicago 13 (1979) and Chicago XIV (1980), brought the band to the end of its contract with Columbia Records, who then released Chicago’s Greatest Hits, Volume II (1981).

After 15 years together, Chicago signed a long-term contract with Warner Brothers Records, and then recruited veteran Bill Champlin and turned to producer David Foster. The result was the million-selling Chicago 16 (1982), featuring the gold single ‘Hard To Say I’m Sorry.’

Their next record, Chicago 17 (1984), was a landmark success for the group. Propelled by the mega-hits ‘Hard Habit To Break,’ and ‘You’re The Inspiration,’ the album sold more than 7 million copies. In 1986, the band was again awarded ‘Favorite Rock Group’ at the American Music Awards. Chicago 18 (1986) yielded the hit ‘Will You Still Love Me?’ and Chicago 19 (1988) was another smash, featuring three Top 10 hits: ‘I Don’t Wanna Live Without Your Love’; the No.1 Grammy-nominated song ‘Look Away’; and ‘You’re Not Alone.’ A fourth song from the album, ‘What Kind Of Man Would I Be?’ became a hit in 1989 when it was included on Greatest Hits (1982 – 1989).

Chicago’s good fortune continued to grow throughout the 90s. The band released Chicago Twenty 1 in 1991. A year later, on July 23, 1992, the group was honored with their own star on the Hollywood Walk of Fame. In 1994, the rights to Chicago ‘s Columbia albums reverted back to the group, and they founded Chicago Records to reissue them.

In 1997, Chicago released their 30th Anniversary celebration record, The Heart of Chicago 1967-1997.

In 1998, the band followed up with The Heart of Chicago 1967 – 1998 Volume II, which represented another fresh collaboration in this case with Roy Bittan of the E Street Band. Subsequently, the band entered the studio to record an entire album with Roy Bittan. The result was Chicago 25, their first holiday album. The release was certified gold in 1999. That same year the band released the live album Chicago 26.

In 2006, Chicago released its 30th album, Chicago XXX. Produced by Jay DeMarcus of the superstar country group Rascal Flatts, Chicago XXX found a large audience of music fans.

In December of 2007, Chicago was honored by the Chicago History Museum with a special exhibit, showcasing historical pieces and band memorabilia. The next year, Billboard Magazine named its Top 100 Artists of All Time. Chicago landed at No. 13, just behind artists such as the Beatles, the Rolling Stones, and Elvis Presley.

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