| ID | Interpret | Skladba | Album | |
| 31. | Cade | I'm Not From Chicago | www.dynagroove.com |  |
| 32. | Cade | I'm Not From Chicago | www.dynagroove.com | |
| 33. | Keith Werner Swing Revue Big Band | Chicago | | |
| 34. | Crosby, Stills, Nash, & Young | Chicago | The 60's: Motion Picture Sound |  |
| 35. | Wilco | Via Chicago | Summerteeth |  |
| 36. | Wilco | Via Chicago | Kicking Television: Live In Chicago [Disc 2] | |
| 37. | lux-1944-10-09-453 | In Old Chicago | Lux Radio Theater | |
| 38. | Wilco | Via Chicago | Summerteeth | |
| 39. | Wilco | Via Chicago | 03.11.1993 Live at Tower Records, N. Clark St. Chicago, IL via WXRT | |
| 40. | Graeme Norgate | Chicago | TimeSplitters 2 | |
| 41. | Fooled By April | Come in, Chicago | Nice to See You | |
| 42. | Guerilla Love Radio - 107.1fm | GLR 107.1fm Chicago | GLR 107.1fm Chicago | |
| 43. | Wilco | Via Chicago | Live--San Diego 4-29-05 | |
| 44. | Wilco | Via Chicago | Massey Hall, Toronto, ON 06.30.07 | |
| 45. | Wilco | Via Chicago | Summerteeth | |
| 46. | Steepwater Band | Down In Chicago | Brother to the Snake | |
| 47. | Sex In Dallas & Biladoll | Chicago | Perpetual Emotion Maschine | |
| 48. | Daily News | chicago | Philly Feed | |
| 49. | Arthur Durkee | Chicago 4'33 | On the Road: A record of changes | |
| 50. | Warren Farren | Chicago 7 | | |
| 51. | Wes Anthony | Chicago | Westet @Greenote | |
| 52. | D.J.Slaider | Chicago | | |
| 53. | Chicago Group | Oh-Chicago | Congress - February 2008 | |
| 54. | Wilco | Via Chicago | Massey Hall, Toronto, ON 06.30.07 | |
| 55. | Baltic Fleet | To Chicago | TRASHMENAGERIE.com | |
| 56. | Steepwater Band | Down In Chicago | Brother to the Snake | |
| 57. | Wilco | Via Chicago | Massey Hall, Toronto, ON 06.30.07 | |
| 58. | Abbie Hoffman | Chicago | Wake Up America! | |
| 59. | Charlie Gehant | Chicago | Album de Charlie Gehant | |
| 60. | Frank Sinatra with Sy Oliver | Chicago | I Remember Tommy | |
