| ID | Interpret | Skladba | Album | |
| 61. | Tommy Dorsey | Chicago | Tommy Dorsey |  |
| 62. | Organ Donor | Chicago | Heaven and Hell |  |
| 63. | sea wolf | chicago | | |
| 64. | nothing nothings | I Like Chicago | Fire Works | |
| 65. | City From Below | Chicago 101 | City From Below | |
| 66. | Tommy Dorsey | Chicago | Tommy Dorsey | |
| 67. | Cade | I'm Not From Chicago | www.dynagroove.com | |
| 68. | Crosby, Stills, Nash, & Young | Chicago | The 60's: Motion Picture Sound | |
| 69. | Cade | I'm Not From Chicago | www.dynagroove.com | |
| 70. | Wilco | Via Chicago | Massey Hall, Toronto, ON 06.30.07 |  |
| 71. | Wilco | Via Chicago | Live--San Diego 4-29-05 | |
| 72. | Chicago | Chicago | | |
| 73. | Arthur Durkee | Chicago 4'33 | On the Road: A record of Changes | |
| 74. | Wilco | Via Chicago | Massey Hall, Toronto, ON 06.30.07 | |
| 75. | Wes Anthony | Chicago | Westet @Greenote | |
| 76. | Wilco | Via Chicago | Massey Hall, Toronto, ON 06.30.07 | |
| 77. | Wilco | Via Chicago | 03.11.1993 Live at Tower Records, N. Clark St. Chicago, IL via WXRT | |
| 78. | Wilco | Via Chicago | Summerteeth | |
| 79. | Wilco | Via Chicago | Summerteeth | |
| 80. | Arthur Durkee | Chicago 4'33 | On the Road: A record of Changes | |
| 81. | Arthur Durkee | Chicago 4'33 | On the Road: A record of changes | |
| 82. | Unknown Artist | Chicago | | |
| 83. | clammbon | chicago | best | |
| 84. | Arthur Durkee | Chicago 4'33 | On the Road: A record of changes | |
| 85. | Sex In Dallas & Biladoll | Chicago | Perpetual Emotion Maschine | |
| 86. | Daily News | chicago | Philly Feed | |
| 87. | Warren Farren | Chicago 7 | | |
| 88. | Wilco | Via Chicago | Kicking Television: Live In Chicago [Disc 2] | |
| 89. | D.J.Slaider | Chicago | | |
| 90. | SCHWARZ, Henrik/AME/DIXON | Chicago | A Critical Mass Live EP | |
