South Side Community Investors Association

11/02/2026

Winter is coming.

Not to jinx it, but property owners have enjoyed historically mild weather across September and October—with little need for heat, even overnight, and extended use of AC units.

November brings cooler temps, and the coming months will test operating budgets with rising gas prices and increased labor and material costs.

Quick punch list if you haven’t started:
Service your boiler/HVAC systems
Inspect your roof
Check your exterior envelope
Stage your salt, shovels, and snow equipment

What did we miss? Add to the checklist in the comments.

10/26/2026

https://blockclubchicago.org/2026/10/23/restored-south-side-community-art-center-set-to-open-next-year-a-miracle-of-a-place/

The oldest continually operating Black arts center in the U.S. is doubling in size, with expanded galleries, a restored ballroom, new classrooms and public archives.

10/26/2026

https://blockclubchicago.org/2026/10/26/young-adult-shelter-coming-to-brainerd-food-production-facility-coming-to-chatham/

Ujima Village’s second shelter will repurpose a closed motel in Brainerd, while CrossTreats snack maker will transform a century-old Chatham building into a manufacturing hub.

10/12/2026

NEGOTIATIONS AHEAD AT CITY HALL

The lead aldermen from the PRO & FAIR groups are set to meet to negotiate the competing housing ordinances.

For South Side Community Investors, the question is simple:
Can the City pass an ordinance that addresses real needs for residents — while NOT increasing the cost to house people and NOT reducing the number of rental units available in our neighborhoods?

Every added cost and every lost unit hurts affordability, especially on the South Side where we are working to preserve and create quality housing.

We are watching this closely. Stay tuned for updates.

10/07/2026

The cost of water continues to go up every year
What can a property owner do?!?

10/06/2026

https://conta.cc/4yt3RK9

Email from First InSite Realty LLC Catch Up on South Side Trends and Opportunities - RSVP Today!       SSCIA Monthly Meeting It’s been too long, and there’s plenty to catch up on. We’re reconvening t

10/06/2026

98% of affordable housing on Chicago’s South Side and across the city is owned by small, independent "mom-and-pop" property owners (per DePaul University).

Yet between surging operating expenses, steep property tax hikes, and looming new regulations, these working-class housing providers are being squeezed to the breaking point.

Small owners keep Chicago housing affordable because they put sweat equity into their buildings—often doing the maintenance and repairs themselves to keep expenses low.

Push them out, and the consequences are predictable: our housing stock will diminish, and rents will rise.

10/01/2026

Property owners: What are you doing with your buildings to get into the spirit of Halloween?

From parades and bar crawls to costume contests and theater productions, there are plenty of ways to celebrate Halloween in Chicago this fall.

10/01/2026

https://www.facebook.com/share/r/1DmqixupBp/

10/01/2026

https://www.multihousingnews.com/the-hidden-risks-behind-office-to-residential-conversions/?utm_source=WhatCountsEmail&utm_medium=Daily%20News&utm_campaign=New%20Daily

Experts examine structural, design and life-safety risks in office-to-multifamily conversions and how developers can address them early.