This thesis explores the ways in which Chicago’s Yiddish-language press responded to the challenges posed by assimilation between 1918-1932. Focusing on two specific Chicago dailies, the Orthodox and Zionist Daily Jewish Courier and the secular and socialist Chicago Jewish Forward, this thesis highlights the diversity of opinions represented in the press and the variety of their responses to the question of Americanization. This thesis ultimately argues that despite their differences in orientation, the Courier and the Forward alike played a dual role in the lives of immigrants; by constructing unique Yiddish-speaking spaces for the immigrant community, Chicago’s Yiddish-language press both challenged the demands of Americanization and facilitated the process of Yiddish speakers becoming “at home” in America. In this way, this thesis adds to the long-standing historiography on role the Yiddish press played in Americanization and provides a much-needed close examination of the Yiddish press in Chicago, which is largely absent in studies of the American Yiddish press.