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According to Billboard's top 100 Chicago had three songs that made it to number one on the charts.

If You Leave Me Now (1976)

Hard to Say I'm Sorry (1982)

Look Away (1988)

Chicago had 5 songs that topped out at #3 beginning with "saturday in the park" in 1972.

They also had two songs each that peaked at #4, 5, 7, 8, 9 and 10, and one more that reached #6.

There were a total of 46 Chicago singles that made the top 100

Chicago had 5 albums that reached #1 in the top 200 album charts:

Chicago V - 6 weeks September & Oct. 1972.

Chicago VI - 1 week (outselling Pink Floyd's Dark Side of the Moon) in August 1973.

Chicago VII - 1 week in April 1974.

Chicago VIII - 2 weeks in May 1975.

Chicago IX - 2 weeks in December 1975.

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Q: How many number 1 hits did Chicago have?
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