Over the weekend of September 13-17, Paprika! sent two student correspondents, Orli Hakanoglu (M. Arch I ‘19) and Jeremy Jacinth (M. Arch II ‘18) to the second Chicago Architecture Biennial, where the Artistic Directors Shannon Johnston and Mark Lee challenged the participants to “Make New History”. The directors identified a number of emerging topics within the proposals, curating installations around the following themes: Building History, Material History, Civic History, and Image History. Throughout the weekend, Orli and Jeremy familiarized themselves with the work of over 140 participants, attended supplementary symposia, and participated in a number of events in the city of Chicago. In this bulletin, Orli and Jeremy reflect on their respective experiences and takeaways. The bulletin also features the work of guest contributor, Jonathan Heckert, Chicago-based architect and adjunct professor at IIT. The following articles attempt to relate the content of the Biennial to the broader field of contemporary architecture by raising questions surrounding authorship, audience, and context.