The media play a pivotal role in framing narratives about complex social issues like homelessness. This study conducts a comparative analysis to evaluate how homelessness is portrayed within print and social media in three Canadian mid-sized cities. We explore similarities and differences between news print media and Facebook conversations on the broad topic of homelessness with respect to temporal distributions of discussions about homelessness, conversations about encampments, the diversity of voices included in social and print media reports, and the use of stereotypical and stigmatizing discourse about homelessness. Our study reveals seasonal variations in discussions about homelessness within traditional media, while social media maintains a more consistent conversation throughout the year. In both media types, however, the discussions about encampments are frequently intertwined with themes of crime and addiction. Moreover, we observe greater inclusion of voices from individuals with lived experience in print media. We find that discussions within both platforms echo common myths associated with homelessness, perpetuating negative conceptions in the broader community. In light of our findings, we advocate for greater editorial oversight on how discussions about homelessness are framed in print media, technological advancements to control negative conversations on social media platforms and encourage the inclusion of voices from those with lived experience. Our research contributes to an underexplored area, as we illuminate the mechanisms of discourse that shape public perceptions and attitudes about homelessness in both print and social media.