Collegiate gothic architecture built in the United States during the early twentieth century has generally been considered an anti-modern reaction to the rapid changes of the period. This article challenges that interpretation by analysing the collegiate gothic architecture and planning of the University of Chicago from its incorporation in 1890 up to 1918, focusing on the work of Shepley, Rutan & Coolidge, which hitherto has been almost entirely neglected. In these decades, the campus changed considerably from the original 1893 quadrangular plan by Henry Ives Cobb. Archival sources are used to trace this shift, with particular attention to three major buildings designed by Charles Coolidge: the Tower Group (1903), Harper Memorial Library (1912) and Ida Noyes Hall (1916). In their architecture and planning, each of these projects set new precedents for the adaptive possibilities of collegiate gothic and changed how the campus related to its urban neighbourhood. From 1900, the university’s leaders consciously opened the campus to its surroundings and realigned it to the Midway Plaisance, the renowned public greenway designed by Frederick Law Olmsted. In doing so, the university pioneered a new campus typology, the academic avenue, which represented a positive embrace of urban life within wider debates on the American city. Through this typology, the university’s collegiate gothic architecture made meaningful connections with Chicago’s progressive civic culture, in consonance with the educational philosophy of its founding president, William Rainey Harper.