| ID | Interpret | Skladba | Album | |
| 61. | City Club of Cleveland | June 20, 2006 featuring Richard D. Cochran, President and CEO, Western Reserve Land Conservancy, Our Regional Vision: Preserving the Land of the Western Reserve | City Club Podcast |  |
| 62. | The Brothers Four | The Brothers Four - This Land Is Your Land | | |
| 63. | Kevn Kinney & Michelle Malone | Miss Miss'ippi | 12/15/05 Caledonia Lounge - Athens, GA | |
| 64. | Angelika Dela Cruz | Miss Na Miss Kita | from dOnNaH's site | |
| 65. | Kedou Bear | Chap 5. Kedou in The Land of Hearts: The Land of Hearts | | |
| 66. | Michael Angelo Christopher Chicago House DJ .com | Michael Angelo Christopher Chicago House DJ .comMichael Angelo Christopher Chicago House DJ .com | Michael Angelo Christopher Chicago House DJ .com | |
| 67. | Steepwater Band | Down In Chicago | Brother to the Snake | |
| 68. | Ekoostik Hookah | Chicago | 2006-12-29 @ Sachsenheim Hall | |
| 69. | Wilco | Via Chicago | Summerteeth |   |
| 70. | Adam & Dee | Chicago | | |
| 71. | Unknown Artist | Chicago | | |
| 72. | Wilco | Via Chicago | Massey Hall, Toronto, ON 06.30.07 | |
| 73. | Wilco | Via Chicago | 03.11.1993 Live at Tower Records, N. Clark St. Chicago, IL via WXRT | |
| 74. | Adam & Dee | Chicago | | |
| 75. | Wilco | Via Chicago | Live--San Diego 4-29-05 | |
| 76. | Guerilla Love Radio - 107.1fm | GLR 107.1fm Chicago | GLR 107.1fm Chicago | |
| 77. | bradbordine | 5-chicago | | |
| 78. | Chicago Group | Oh-Chicago | Congress - February 2008 | |
| 79. | SHOCK STARS | End Of Chicago | End Of Chicago | |
| 80. | Arthur Durkee | Chicago 4'33 | On the Road: A record of Changes | |
| 81. | City From Below | Chicago 101 | City From Below | |
| 82. | Steepwater Band | Down In Chicago | Brother to the Snake | |
| 83. | Frank Sinatra with Sy Oliver | Chicago | I Remember Tommy | |
| 84. | Alberta Cross | Old Man Chicago | The Thief & The Heartbreaker | |
| 85. | Fooled By April | Come in, Chicago | Nice to See You | |
| 86. | Baltic Fleet | To Chicago | TRASHMENAGERIE.com | |
| 87. | Frank Sinatra | Chicago | Capitol Years Disc 20 | |
| 88. | Frank Sinatra | Chicago | Capitol Years Disc 20 | |
| 89. | Frank Sinatra | Chicago | | |
| 90. | Hedningarna | Chicago | Kaksi! | |
