In 2025, Hales Property Management delivered $254,104.78 in condo association insurance savings across its Chicago client portfolio. Six buildings each saved more than $10,000 on their annual premiums. The renewal process was overseen by staff who specialize in contract management, with a strong focus on identifying cost savings while maintaining, and where possible, enhancing existing service levels. The team follows a proactive procurement cycle beginning approximately 60 days prior to each policy renewal date to ensure ample time for market analysis, negotiation, and evaluation of coverage options.
This case study covers three of those buildings: what each board faced going into the renewal, what changed during the procurement cycle, and what the outcomes look like.
The Chicago Insurance Backdrop in 2025
The commercial insurance market has seen 10% to 20% year-over-year premium increases industry-wide, driven in part by national natural disaster activity that ripples back through every market.
Buildings flagged as higher-risk by carriers have seen renewal increases as high as 30%. In that environment, a flat renewal is a win. A reduction takes deliberate work from both the management company and the association.
Insurance is one of the largest line items in most Chicago condo budgets, competing with utilities and reserve contributions for the top expense slot. A few thousand dollars of premium savings on one building, multiplied across a portfolio, adds up.
How Hales Approaches Each Renewal
The procurement cycle starts approximately 60 days before each policy renewal. The first step is requesting loss history from the current carrier, which is required by any carrier that will submit a competing quote.
If the association’s current insurance agent is captive to a single carrier, Hales engages an independent insurance brokers who specializes in condominium insurance. Unlike captive agents, independent brokers have access to multiple insurance carriers and can competitively market the association’s coverage to identify the most favorable options. To maximize market exposure, Hales works with several specialized brokers while carefully coordinating the process to avoid market conflicts. This is important because insurance carriers typically grant exclusive access to the first broker or agent that submits a quote request for a particular property, preventing subsequent brokers from obtaining competing proposals from that same carrier.
About one to two weeks before each renewal, the results are compiled and summarized for the board: the existing renewal proposal, the alternative options identified through market shopping, and a recommendation. In roughly half of cases, the existing carrier still comes back with the most competitive number, and the shopping exercise confirms that. In the other half, a better option emerges, and the board decides whether to switch.
Building 1: The Aluminum Wiring Retrofit at a Historic Building
A historic Chicago condominium had original aluminum wiring throughout, which carriers consistently rated as high-risk. For several years, the association faced repeated declines from new carriers and 15% to 30% annual increases, with the one carrier willing to maintain coverage.
The board decided to retrofit. Over the past year, the association completed a full conversion to copper wiring across the entire building, a meaningful capital investment that the board approved with the long-term insurance trajectory in mind.
The most recent renewal came back at approximately 4%. Compared to the 15% to 30% increases the building had absorbed in prior years, that 4% reflects a fundamentally different underwriting position. A new carrier has also expressed interest in providing competitive quotes at the next renewal cycle.
The full impact will become visible at the next renewal, when broader carrier competition is expected to open up. The early indicators are strong, and the case shows how a substantial capital project can change how carriers price a building’s risk.
Building 2: A Roof Restoration That Reversed a Non-Renewal
Another Chicago condo building received a non-renewal notice from its existing carrier, citing the roof condition as the primary concern. Non-renewals from a current carrier are serious. Under Illinois law, the carrier must give 30 or 60 days’ notice, leaving a narrow window to either remediate the issue or find a new market.
The association coordinated a full roof restoration in response, completing the work within the notice window. Hales documented the completed restoration for the carrier.
Once the roof work was finished and submitted, the carrier rescinded the non-renewal notice. Coverage continued without interruption, and premium savings followed at the renewal once the building’s risk profile had improved. The board avoided a forced carrier search under a tight deadline, which is the kind of situation that often results in worse coverage at a higher cost.
Building 3: A 62-Unit Association That Switched Carriers for $10,895 in Savings
A 62-unit Chicago condominium association was placed with a higher-cost carrier when Hales began coordinating the renewal. Through the 60-day procurement process, Hales worked with an independent broker specializing in condo insurance to shop the market.
The shopping turned up a different carrier writing condo coverage at a meaningfully lower rate. The board reviewed the alternative option alongside the existing renewal proposal in the standard summary. After comparing the two, the board approved the switch.
The carrier change produced approximately $10,895 in savings over the policy term while maintaining equivalent coverage. This pattern is common when Hales onboards a new client whose insurance has not been competitively shopped in years. The market moves, and a carrier that was the best fit at the last renewal may not be at the next one.
What This Means for Other Chicago Condo Boards
Three lessons surface from the 2025 work that other Chicago condo boards can apply directly.
Capital work shows up in insurance pricing. The aluminum wiring retrofit and the roof restoration both produced measurable changes in their buildings’ underwriting positions. Boards weighing whether to fund a significant capital project should ask their management firm to model the insurance impact alongside the project cost. The condo association insurance checklist outlines what carriers typically look at and what boards can prepare in advance.
Independent brokers who specialize in condo insurance are different. A captive agent representing a single carrier cannot shop the market. A general independent broker covers many lines of business. An independent broker focused on condo insurance brings specific knowledge of condo law requirements and access to carriers that actively want condo business. The difference shows up in pricing.
Shopping every renewal is worth it, even when no switch happens. Half of the 2025 renewals came back with the existing carrier as the best option. Those boards still got confirmation that the market had been tested. None of them renewed blind.
The $254K total reflects work done across the portfolio by associations completing capital projects, keeping claim histories clean, and coordinating with a procurement process built to test every renewal. The savings are the visible outcome. The underlying work belongs to the boards.
Working With Hales on Insurance Procurement
Hales Property Management coordinates insurance procurement as part of its association management services for condo boards. Boards interested in how this procurement approach would work for their building can request a proposal or call 312.666.0149.
