The Avery Review, a digital journal about books, buildings, and other architectural media, makes its print debut with a thematic broadsheet edition about the city of Chicago. Coinciding with the inaugural Chicago Architectural Biennial, this issue addresses the historic imagination of the city (including figures of myth like Frank Lloyd Wright, Mies van der Rohe, and even John Dillinger) and possibilities for the contemporary urban landscape (including discussions of placemaking, contemporary cultural monuments, and infrastructural parks). Selected pieces from the Avery Review's first year are republished alongside these commissioned essays on Chicago. Together these texts claim the critical essay as a space in which to test one's own intellectual commitments, to enter into and advance a conversation about the pasts and futures of urban architectural thought.