Since last year’s Best of the South Side (BoSS), a new engagement editor, art director, editor-in-chief, and interim publisher have joined South Side Weekly. So, we appreciate your patience and grace, dear readers. Because this year, more than most, BoSS is brought to you by newbies.
Ironically, we newbies have heard—from the hardbitten, dedicated vets—that BoSS has been made in wildly different ways, year to year. These shifts have occurred for a range of reasons, including moving from a nearly-all volunteer base to a freelancer model and accommodating staff transitions. Nevertheless, we all know the assignment, every September—we aim to engage, illuminate and celebrate the South Side, neighborhood by neighborhood.
This year, we hope features and longer neighborhood profiles will prompt deep thinking about this place we call home. How are we doing, collectively? What patterns are static in the region, and what things are changing? How are our communities evolving, over time?
Included are reporting on how the Southwest Side has been confronting ICE since the beginning of last year’s Midway Blitz, and an exploration of why African Americans are leaving Chicago. Writing through a historical lens meant placing a beloved Bridgeport bar in the context of its place in the former Lithuanian downtown, showing how religious spaces in Roseland and Woodlawn have adapted to accommodate new congregations and uses, and how community centers in Chinatown and Pilsen have weathered shifts in immigration, crime, and local politics.
Our staff has been energized by our work with many new writers, reporters, photographers, and illustrators to complete this issue, the largest BoSS since 2022. And we’ve learned more than we ever anticipated about the 20 neighborhoods—from Brighton Park to Roseland—covered here. About 1 million people live on Chicago’s South Side. We know how fortunate we are to work to honor your stories every day. We also hope you’ll reach out—on social or by email—to let us know what you want to see more in the next BoSS, as well as upcoming issues.
Final announcements: You can pick up copies of the Weekly in every public library on the South Side, and we’re in new locations in every South Side neighborhood! Check out our new distribution at bit.ly/ssw-distro-2026.
And for the remainder of the year, the Weekly will publish three print issues: on October 29 (our election issue), November 19, and December 10.
Cover art by Jaz Rodriguez
