| ID | Interpret | Skladba | Album | |
| 91. | Sex In Dallas & Biladoll | Chicago | Perpetual Emotion Maschine |  |
| 92. | Cade | I'm Not From Chicago | www.dynagroove.com | |
| 93. | Seung Sahn Zen Master | Chicago | February 1977 | |
| 94. | Jeff Tweedy & Jay Bennett | Via Chicago | 1999/07-25 Old Town School of Folk Music Festival, Chicago, IL | |
| 95. | ekoostik hookah | Chicago | 12-31-98 - Newport Music Hall - Cols., OH |  |
| 96. | Andrew Bracken | Chicago | alectricity 3 | |
| 97. | Cade | I'm Not From Chicago | www.dynagroove.com | |
| 98. | bradbordine | 5-chicago | | |
| 99. | Daily News | chicago | Philly Feed | |
| 100. | Groove Armada | Chicago | Vertigo | |
| 101. | Jeff Tweedy & Jay Bennett | Via Chicago | Old Town School of Folk Music Fest, 7/25/99 | |
| 102. | Steve Carell, Amy Sedaris, Paul Dinello, Stephen Colbert, Mitch Rouse and Others | Welcome to Chicago | The Best of Second City | |
| 103. | Frank Sinatra | Chicago | Capitol Years Disc 20 |  |
| 104. | Seung Sahn Zen Master | Chicago | February 1977 | |
| 105. | Wilco | Via Chicago | Massey Hall, Toronto, ON 06.30.07 | |
| 106. | Wes Anthony | Chicago | Westet @Greenote | |
| 107. | clammbon | chicago | best | |
| 108. | Kiki Dee | 05 Chicago | In Concert 1977 | |
| 109. | Ekoostik Hookah | Chicago | 1999-05-29 - Buckeye Lake Music Center - Hookahville XI | |
| 110. | ekoostik hookah | Chicago | Jamaica 4-16-02 | |
| 111. | ekoostik hookah | Chicago | Jamaica 4-16-02 | |
| 112. | Arthur Durkee | Chicago 4'33 | On the Road: A record of changes | |
| 113. | ekoostik hookah | Chicago | 6-19-99 - Mariner's Beach Club - Negril, JA | |
| 114. | Arthur Durkee | Chicago 4'33 | On the Road: A record of changes | |
| 115. | ekoostik hookah | E: Chicago> | Hookahville Sp2K 5/26/00 set 2 | |
| 116. | Arthur Durkee | Chicago 4'33 | On the Road: A record of Changes | |
| 117. | Arthur Durkee | Chicago 4'33 | On the Road: A record of Changes | |
| 118. | Hedningarna | Chicago | Kaksi! | |
| 119. | Unknown Artist | Chicago | | |
| 120. | ekoostik hookah | Chicago | Hookahville Sp2K 5/26/00 set 2 | |
