| Date | Artist | Opening act(s) | Tour / concert name | Attendance / Capacity | Revenue | Notes |
| August 21, 1937 | Lily PonsRudy ValleeJascha HeifetzBobby Breen | — | Chicagoland Music Festival | — | — | |
| August 15, 1964 | Johnny CashJune Carter | — | — | — | |
| August 9, 1966 | Barbra Streisand | — | An Evening with Barbra Streisand Tour | — | — | First solo headliner |
| July 18, 1970 | Performers Chicago Illinois Speed Press The Illusion Pig Iron Iggy Pop and The Stooges Dream Leon Russell MC5 Funkadelic Mason Proffit Bush Happy Day It Doesn't Matter Joe Kelley Blues Band Bloomsbury People | — | WCFL's Big Ten Summer Music Festival | — | — | |
| June 4, 1977 | Emerson, Lake & Palmer | FoghatThe J. Geils BandClimax Blues Band | ELP Works/Super Bowl of Rock | 63,848 / 65,000 | $647,172 | |
| June 19, 1977 | Pink Floyd | | In the Flesh Tour | 67,000 / 67,000 | $670,000 | |
| July 9, 1977 | Lynyrd Skynyrd | Point Blank | | 77,197 | — | |
| July 10, 1977 | Ted Nugent | Lynyrd SkynyrdREO SpeedwagonJourney.38 Special | Super Bowl of Rock | 63,870 / 65,000 | $627,995 | First solo male headliner |
| August 13, 1977 | Peter Frampton | Bob Seger and the Silver Bullet BandRick DerringerUFO | Super Bowl of Rock | 47,365 / 65,000 | $476,007 | |
| September 24, 1977 | Chicago | — | Lincoln Park Zoo Benefit | — | — | |
| July 8, 1978 | The Rolling Stones | JourneySouthside Johnny & The Asbury JukesPeter Tosh | The Rolling Stones US Tour 1978 | 70,725 / 70,725 | $919,425 | |
| August 26, 1978 | Parliament-Funkadelic | The Bar-KaysCon Funk ShunA Taste of Honey | Funk Fest | — | — | |
| July 19, 1980 | Smokey Robinson | The O'Jays | Budweiser Superfest | 41,322 / 58,000 | $702,474 | |
| August 10–18, 1983 | Performers Buddy Guy Junior Wells The Beach Boys Stevie Ray Vaughan and Double Trouble The Association The Hollies The Kind Laura Branigan | — | ChicagoFest | — | — | |
| August 9, 1985 | Bruce Springsteen and the E Street Band | — | Born in the U.S.A. Tour | 71,222 / 71,222 | $1,228,500 | |
| July 31, 1987 | Madonna | Level 42 | Who's That Girl World Tour | 47,407 / 47,407 | $1,066,658 | |
| July 29, 1990 | Paul McCartney | — | The Paul McCartney World Tour | 55,630 / 55,630 | $1,807,975 | |
| June 22, 1991 | Grateful Dead | — | Summer Tour 1991 | 58,416 / 58,416 | $1,573,891 | |
| June 25, 1992 | Grateful Dead | Steve Miller Band | Summer Tour 1992 | 110,670 / 118,394 | $3,116,492 | |
| June 26, 1992 |
| June 18, 1993 | Grateful Dead | Sting | Summer Tour 1993 | 115,239 / 115,239 | $3,041,690 | |
| June 19, 1993 |
| July 12, 1994 | Pink Floyd | — | The Division Bell Tour | 51,981 / 51,981 | $2,056,105 | |
| July 23, 1994 | Grateful Dead | Traffic | Summer Tour 1994 | 111,002 / 111,002 | $3,546,758 | |
| July 24, 1994 |
| September 11, 1994 | The Rolling Stones | Lenny Kravitz | Voodoo Lounge Tour | 90,303 / 90,303 | $4,194,320 | |
| September 12, 1994 |
| July 8, 1995 | Grateful Dead | The Band | Summer Tour 1995 | 113,327 / 113,327 | $3,694,431 | |
| July 9, 1995 | Final concert by the band. |
| July 11, 1995 | Pearl Jam | Bad ReligionOtis Rush | Vitalogy Tour | 47,824 / 47,824 | $1,028,216 | Played on the Grateful Dead's stage |
| September 14, 1996 | Little Feat | Taj Mahal | | — | — | |
| June 27, 1997 | U2 | Fun Lovin' Criminals | PopMart Tour | 116,912 / 127,500 | $5,956,587 | |
| June 28, 1997 |
| June 29, 1997 |
| July 18, 1997 | Performers Bad Religion Blink-182 Descendents Hed PE Jimmy 2 Times Lagwagon Latex Generation Less Than Jake Limp Bizkit The Mighty Mighty Bosstones Millencolin Murder City Devils Orange 9mm Pennywise Reel Big Fish Sick of It All Snot Social Distortion Strung Out Sugar Ray Trading Bryson Vision of Disorder White Kaps | — | Vans Warped Tour | — | — | |
| September 23, 1997 | The Rolling Stones | Blues Traveler | Bridges to Babylon Tour | 107,186 / 107,186 | $6,260,000 | |
| September 25, 1997 |
| May 10, 1998 | George Strait | — | Country Music Festival Tour | 45,486 / 45,486 | $1,813,825 | |
| April 25, 1999 | George Strait | — | Country Music Festival Tour | 36,022 / 36,022 | $1,402,194 | |
| May 13, 2000 | Wilco | — | | — | — | |
| June 29, 2000 | Dave Matthews Band | Ben Harper and the Innocent CriminalsOzomatli | The Summer 2000 Tour | 115,006 / 115,006 | $5,175,270 | |
| June 30, 2000 |
| June 16, 2001 | NSYNC | BBMak3LWDream | PopOdyssey | 85,650 / 103,903 | $4,739,359 | |
| June 17, 2001 |
| July 6, 2001 | Dave Matthews Band | Buddy GuyAngélique Kidjo | The Summer 2001 Tour | 103,675 / 103,675 | $4,834,864 | |
| July 7, 2001 |
| September 10, 2005 | The Rolling Stones | Los Lonely Boys | A Bigger Bang | 55,046 / 55,046 | $7,231,427 | |
| July 21, 2006 | Bon Jovi | Nickelback | Have a Nice Day Tour | 52,612 / 52,612 | $3,988,455 | |
| October 11, 2006 | The Rolling Stones | Elvis Costello and the Imposters | A Bigger Bang | 33,296 / 33,296 | $4,020,721 | |