Cosmic asked for diversity. I've been attending concerts and club dates since the mid 1950s. Every kind of music: rock, folk, classical, jazz and ethnic. Choosing some standouts, without a three page post, in tiny print, will be tough, but here it goes:
*The Who, I've seen them every time they were in Chicago; one of the best was the first, the "Tommy" tour in 1969, at a club called The Kinetic Playground
*James Brown and The Fabulous Flames, 1966 in Dallas
*Erroll Garner, Bill Evans, Oscar Peterson and The MJQ, at various Chicago clubs
*Luciano Pavarotti, in his first concert performance in Chicago
*Andres Segovia, I sat on stage with other lucky audience members, during one of his last concerts, in a SRO performance in Orchestra Hall, 1987
*Ravi Shankar, in the same venue, many times
*Baby Huey and The Babysitters, Aorta, The Cryan' Shames and The Flock, Chicago legends
*Bruce Springsteen, "Born To Run" tour, best of the many shows I attended
*Sir Georg Solti conducting the CSO, in an incredible performance of Beethoven's Ninth
*Bob Gibson and Bob Camp at The Gate of Horn
*Jethro Tull, many times, best was "Thick As A Brick" tour
*Miles Davis at The Plugged Nickel
*Tony Bennett, at Ravinia
*Darius Rucker, "True Believers" tour
*The Beatles, 1964, Chicago International Amphitheater, couldn't hear much though
Those are a few high points in a long eclectic ride.