The holiday season is arriving in Wrigleyville, the Cubs are making offseason moves, and two major Lakeview developments are drawing public attention. Here’s what’s happening around Southport Corridor, Wrigleyville and Lakeview during the week of November 9.

Southport Corridor business news

Southport Grocery & Cafe prepares for its final weeks

Southport Grocery and Cafe storefront at 3552 North Southport Avenue in Chicago
Southport Grocery & Cafe on Southport Avenue.

After 23 years, Southport Grocery & Cafe plans to close December 31, 2026. Dollop Finer Diner is scheduled to open at 3552 N. Southport Ave. on February 1, 2027. Read our earlier coverage.

At the Music Box Theatre

Music Box Theatre vertical sign and marquee on Southport Avenue Chicago
The Music Box Theatre on Southport Avenue.

The Music Box Theatre’s November 12–19 lineup includes The Addams Family, Addams Family Values, Evil Dead II, Ponyo, Gremlins 2: The New Batch, Thelma & Louise, It Came from Outer Space, Once Upon a Time in Harlem, Ashes and Diamonds, Kanal, Magnificent Bodyguards, La bola negra, Fatherland, Mouse, Boom!, Money from Home, Sawyer Avenue, Sunday Afternoon, and Nirvanna The Band The Show The Movie The Commentary Track. See showtimes and tickets.

Wrigleyville holiday bars begin opening

Santa Baby Christmas pop up bar illuminated with holiday lights in Wrigleyville Chicago
Holiday pop-up bars are returning across Wrigleyville.

Wrigleyville Wonderland brings more than 20 holiday-themed bars and restaurants to the neighborhood through January 31, 2027. Elf’d Up at Stretch Chicago opened November 7. Home Run Holidays at Brickhouse Tavern follows November 11; Almost Home Alone, Christmas at Kincade’s and Jingle Junkie at Roadhouse 66 open November 13; and The Polar Bear at Cubby Bear and Santa’s Scoreboard at Sports Corner open November 16.

Christkindlmarket and Winterland holiday festivities at Gallagher Way outside Wrigley Field Chicago
Christkindlmarket and Winterland return to Gallagher Way November 20.

Christkindlmarket and Winterland open at Gallagher Way November 20, alongside more holiday bar openings. See our complete guide to 22 holiday bars, TBOX and Winterland.

Wrigley Field security construction continues

Security bollard construction trench on Waveland Avenue outside Wrigley Field in Chicago 2026
Security work along Waveland Avenue near Wrigley Field.

The roughly $32 million bollard security project continues ahead of the 2027 MLB All-Star Game. Sheffield Avenue is closed to vehicles between Addison and Waveland through early December. Waveland is eastbound-only between Clark and Sheffield, with restrictions expected into early March. Addison sidewalk work continues into January, and Clark Street sidewalk work is planned for November and December. Read our full construction update.

Chicago Cubs offseason: awards, free agency and trade rumors

Chicago Cubs W flag flying from a Southport Corridor home in Chicago
Cubs fans in the Southport Corridor have plenty to follow this offseason.

Pete Crow-Armstrong is an MVP finalist

Pete Crow-Armstrong joins Shohei Ohtani and Brice Turang as National League MVP finalists. The winner is scheduled to be announced Thursday, November 12. Crow-Armstrong also earned his second consecutive Gold Glove.

Three Cubs are Silver Slugger finalists

Crow-Armstrong, Alex Bregman and Seiya Suzuki are finalists for Silver Slugger Awards, with winners scheduled for November 17. The Cubs also received a team offensive nomination.

Free agency and roster moves

Seiya Suzuki received a one-year, $23.15 million qualifying offer, with a November 17 decision deadline. Jacob Webb re-signed on a one-year agreement worth $2.5 million guaranteed with a 2028 club option, and Chicago claimed reliever Eric Orze from Minnesota. Clay Holmes declined a mutual option, Matthew Boyd entered free agency, Carson Kelly voided his mutual option, and the Cubs declined options on Colin Rea, Caleb Thielbar and Hunter Harvey.

Pitching remains a central offseason question. ESPN’s Jeff Passan has reported strong Cubs interest in Detroit ace Tarik Skubal, though no trade is assured. MLB general manager meetings run November 9–12 in Las Vegas. The league’s collective bargaining agreement is scheduled to expire December 1. More Cubs offseason reporting.

Lakeview development and real estate

920 W. Diversey proposal heads to a community meeting

Architectural rendering of earlier 920 West Diversey Parkway mixed use development proposal in Chicago
Earlier design proposal for 920 W. Diversey; the proposed unit count has since changed.

A 44th Ward community meeting is scheduled for Tuesday, November 10 at 5:30 p.m. for the mixed-use proposal at 920 W. Diversey Pkwy., near the Brown Line. The latest plan calls for 52 apartments and ground-floor retail, down from 56 units in the earlier proposal. Read our original coverage.

Public feedback deadline for 2800 N. Sheridan

Residents have until Thursday, November 12 to weigh in on a proposed 28-story, 355-unit apartment building at Sheridan and Diversey, including fitness, retail and parking space. A demolition permit was issued in July for the vacant medical building, but the larger project still requires approvals. More on the proposal.

Lakeview dog park project delayed

The Lakeview Dog Friendly Area is temporarily on hold after the lowest qualified construction bid exceeded the budget. The Chicago Park District plans to explore design changes with stakeholders and seek new bids early next year.

44th Ward alderman faces two challengers in 2027

Lakeview Ald. Bennett Lawson is facing his first contested election for the 44th Ward seat, with Dennis “DJ” Doran and Kalen Luciano challenging the incumbent in the February 23, 2027 municipal election. Lawson succeeded longtime Ald. Tom Tunney in 2023. Read our full report on the 44th Ward race.

Coming up this week

  • November 10: 920 W. Diversey community meeting, 5:30 p.m.
  • November 12: 2800 N. Sheridan feedback deadline; NL MVP announcement.
  • November 13: More Wrigleyville holiday bars open.
  • November 16: The Polar Bear and Santa’s Scoreboard open.
  • November 19: Lakeview East Holiday Tree Lighting, 6 p.m., Clark Street Dog, 3040 N. Clark St.
  • November 20: Christkindlmarket and Winterland open at Gallagher Way.

Have a neighborhood tip, opening, closing or development update? Let Southport Corridor News & Events know. Follow along for neighborhood news throughout the week.

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