Roscoe Village Winterfest Returns December 5–6, 2026
Roscoe Village Winterfest returns December 5–6, 2026, with a weekend focused on neighborhood holiday traditions, family activities and local shopping.
Southport Holiday Cocktail Crawl Returns December 4, 2026
Sip, shop and celebrate on Southport Avenue Friday, December 4, 2026, as the Southport Holiday Cocktail Crawl returns with samples, carolers and Santa.
Lakeview Tree Lighting Returns November 22, 2026, at Lincoln and Wellington
Lakeview's 2026 holiday tree lighting takes place November 22 at Lincoln and Wellington, with carolers, goody bags and a special North Pole visitor.
Southport Grocery & Cafe to Close at Year’s End After 23 Years on Southport Avenue
After 23 years, Southport Grocery & Cafe will close at the end of 2026 — and owner Lisa Santos confirmed that Dollop Diner, the local Chicago chain's Andersonville brunch spot,…
Oktoberfest Chicago Returns to Southport Corridor This Weekend
One of the Southport Corridor’s biggest fall traditions is back this weekend as St.
Trick or Treat on Southport Returns October 26 with Candy, Costumes and Halloween Fun
One of the Southport Corridor’s favorite fall traditions is back. Trick or Treat on Southport returns Monday, October 26, from 4 to 7 p.m.
Celebrate the Heartwarming Conclusion to “Oliver the Ornament” Series with a Special Discount
As the holiday season draws near, we’re thrilled to share exciting news about a beloved series that has warmed hearts and brought families closer together.
Celebrate Annual Lakeview’s Tree Lighting!
Sunday, Nov. 19 at 6pm at St. Alphonsus Church – details ! Located outside of St.
‘Tis the season, it’s the annual Southport Holiday Stroll and Cocktail Crawl!
It’s that time of year again for the Lakeview Roscoe Village Holiday Stroll and Cocktail Crawl!
Sound of Music Sing-a-Long returns to Music Box Theatre Thanksgiving Weekend
The tunes of “The Sound of Music” will fill the Music Box Theatre, setting the stage for a joyous experience starting Thanksgiving weekend .
The best place for a Christmas Tree in the area? Ivy’s Christmas Trees
We’ve had a ton of DM’s throughout the years on the best place for a Christmas Tree in the area, and Ivy’s is the place to go. They are located…
Southport’s Annual Holiday Cocktail Crawl details this Friday, December 2, 2022
From the Lakeview Chamber of Commerce , “The Southport Holiday Stroll is a longstanding tradition in West Lakeview where break out the holly and stay open