| ID | Interpret | Skladba | Album | |
| 61. | ekoostik hookah | Chicago | Jamaica 4-16-02 |   |
| 62. | ekoostik hookah | Chicago | Hookahville Sp2K 5/26/00 set 2 | |
| 63. | ekoostik hookah | Chicago | 12-31-98 - Newport Music Hall - Cols., OH | |
| 64. | Ekoostik Hookah | Chicago | 1999-05-29 - Buckeye Lake Music Center - Hookahville XI | |
| 65. | Chicago | Chicago | |  |
| 66. | Ekoostik Hookah | Chicago | 2006-12-29 @ Sachsenheim Hall | |
| 67. | Adam & Dee | Chicago | | |
| 68. | Arthur Durkee | Chicago 4'33 | On the Road: A record of changes | |
| 69. | Adam & Dee | Chicago | | |
| 70. | nothing nothings | I Like Chicago | Fire Works | |
| 71. | Fooled By April | Come in, Chicago | Nice to See You | |
| 72. | Cade | I'm Not From Chicago | www.dynagroove.com | |
| 73. | Wilco | Via Chicago | 03.11.1993 Live at Tower Records, N. Clark St. Chicago, IL via WXRT | |
| 74. | Jeff Tweedy & Jay Bennett | Via Chicago | 1999/07-25 Old Town School of Folk Music Festival, Chicago, IL | |
| 75. | Jeff Tweedy & Jay Bennett | Via Chicago | Old Town School of Folk Music Fest, 7/25/99 | |
| 76. | Cade | I'm Not From Chicago | www.dynagroove.com | |
| 77. | Wilco | Via Chicago | Live--San Diego 4-29-05 | |
| 78. | Cade | I'm Not From Chicago | www.dynagroove.com | |
| 79. | Cade | I'm Not From Chicago | www.dynagroove.com | |
| 80. | sea wolf | chicago | | |
| 81. | Daily News | chicago | Philly Feed | |
| 82. | Wilco | Via Chicago | Massey Hall, Toronto, ON 06.30.07 | |
| 83. | bradbordine | 5-chicago | | |
| 84. | Wilco | Via Chicago | Massey Hall, Toronto, ON 06.30.07 | |
| 85. | Wilco | Via Chicago | Kicking Television: Live In Chicago [Disc 2] | |
| 86. | Keith Werner Swing Revue Big Band | Chicago | | |
| 87. | Wilco | Via Chicago | Summerteeth | |
| 88. | Wes Anthony | Chicago | Westet @Greenote | |
| 89. | Guerilla Love Radio - 107.1fm | GLR 107.1fm Chicago | GLR 107.1fm Chicago | |
| 90. | Cade | I'm Not From Chicago | www.dynagroove.com | |
