Southport Corridor in Photos

Fuji, the Southport Golden, outside Crosby's Kitchen on Southport Avenue in Chicago

Southport Avenue is a neighborhood best explored on foot, one storefront and one familiar face at a time. This photo archive captures changing storefronts, favorite restaurants, street festivals, historic homes, Cubs celebrations, and everyday scenes worth remembering. Explore the sections below for a look at Southport through the years. The captions identify the streets, businesses, and years wherever known.

1. The Avenue by Season

From summer and spring to fall colors and holiday lights, these photographs show how Southport changes throughout the year — including Christmas scenes from 2013, 2015 and 2021.

2. Storefronts & Signs

The corridor letter by letter: the hand-picked signs of 2015 alongside the storefronts of the October 2026 walk-through — closing with the national arrivals of the past decade, from J.Crew and Lululemon to Vuori, Arc’teryx and Reformation, two of them greeted by Fuji, the Southport Golden.

3. Festivals & Events

Taco Fest, the Halloween crawl, St. Patrick’s Day and the holiday strolls: the days the street closes and the neighborhood comes out.

4. Wrigley & the Cubs

November 2016: the neighborhood around Wrigley Field in the days after the Cubs finally won the World Series — plus a coda from 2017: the corridor’s own golden retriever under the marquee.

5. Dogs of Southport

From the Dog Days portraits of Fuji and Hudson to the 2026 Golden Balloons fundraiser, the corridor’s most photographed residents walk on four legs.

6. The Corridor Today

The corridor as it stands today, walked in two successive falls: first the fall 2024 tour — storefronts old and new along Southport Avenue, the Brown Line overhead, and the quiet residential blocks behind the avenue — then an October 2026 walk from Belmont to Addison: new storefronts beside old stone, dining and drinking woven through the shopping, pumpkins under the Brown Line tracks.

7. Great Homes of the Southport Corridor

Greystones and Victorians, turrets and wraparound porches — the best of the blog’s Great Homes and Dream Home posts, 2013 to today: the houses that make people slow down on the corridor’s side streets.

8. Throwback Thursday: The Corridor As It Was

Before the boutiques: streetcars on Southport, coal yards around Wrigley, the largest German restaurant in Chicago, and a department store’s last days. Drawn from a decade of the blog’s #TBT posts — the avenue and the ballpark as they were, from Blaine School’s first year in 1895 to the great blizzard of 2011.