| ID | Interpret | Skladba | Album | |
| 91. | Abbie Hoffman | Chicago, Chicago | Wake Up America! |  |
| 92. | Frank Sinatra | Chicago | Frank Sinatra - Collectors Se |   |
| 93. | Wilco | Via Chicago | Live--San Diego 4-29-05 | |
| 94. | Wilco | Via Chicago | Massey Hall, Toronto, ON 06.30.07 | |
| 95. | Unknown Artist | Chicago | | |
| 96. | Fooled By April | Come in, Chicago | Nice to See You | |
| 97. | bradbordine | 5-chicago | | |
| 98. | clammbon | chicago | best | |
| 99. | Andrew Bracken | Chicago | alectricity 3 | |
| 100. | Seung Sahn Zen Master | Chicago | February 1977 | |
| 101. | Seung Sahn Zen Master | Chicago | February 1977 | |
| 102. | Arthur Durkee | Chicago 4'33 | On the Road: A record of Changes | |
| 103. | Arthur Durkee | Chicago 4'33 | On the Road: A record of Changes | |
| 104. | Arthur Durkee | Chicago 4'33 | On the Road: A record of changes | |
| 105. | Wilco | Via Chicago | 03.11.1993 Live at Tower Records, N. Clark St. Chicago, IL via WXRT | |
| 106. | Wilco | Via Chicago | Kicking Television: Live In Chicago [Disc 2] | |
| 107. | Wilco | Via Chicago | Summerteeth | |
| 108. | Frank Sinatra | Chicago | | |
| 109. | Warren Farren | Chicago 7 | | |
| 110. | Wilco | Via Chicago | Massey Hall, Toronto, ON 06.30.07 | |
| 111. | Frank Sinatra | Chicago | | |
| 112. | Wilco | Via Chicago | Summerteeth | |
| 113. | Daily News | chicago | Philly Feed | |
| 114. | Sex In Dallas & Biladoll | Chicago | Perpetual Emotion Maschine | |
| 115. | Frank Sinatra | Chicago | Capitol Years Disc 20 | |
| 116. | Frank Sinatra | Chicago | Capitol Years Disc 20 | |
| 117. | Wes Anthony | Chicago | Westet @Greenote | |
| 118. | Wilco | Via Chicago | Massey Hall, Toronto, ON 06.30.07 | |
| 119. | Wilco | Via Chicago | Summerteeth | |
| 120. | Arthur Durkee | Chicago 4'33 | On the Road: A record of changes | |
