When choosing a condo in Chicago, many people weigh the options between downtown high-rises and vintage buildings. Recently, the surge in insurance premiums has significantly affected this choice and its impact on management fees.

As of 2026, the median price for condos in Chicago is around $438,000. Prices for condos and townhomes increased by 5.5 percent from February 2025 to February 2026, but during the same period, the transaction volume decreased by 11 percent, and inventory dropped by nearly 25 percent. Overall, by May 2026, the median price in the city rose to $420,000, a 6.3 percent increase from a year earlier, with the average market stay at 47 days, shorter than the national average of 58 days. With inventory decreasing and prices rising, there is less room for negotiation when choosing a condo compared to the past.

Downtown high-rises, equipped with doormen, multiple elevators, and spacious community areas, have management fees ranging from $400 to $1,200 per month, and buildings with on-site staff can exceed $600. In contrast, vintage buildings like greystones or courtyards have lower management fees due to fewer shared facilities, but this also increases the risk of deferred maintenance. The citywide average is around $425 per month, generally fluctuating between $300 and $600.

Insurance premiums are a common variable affecting both types. Condo and HOA insurance premiums rose by about 15 percent in 2023 alone, with increases continuing into 2024 and 2025. Management fees in Chicago and nearby suburbs increased by about 10 percent in 2024, with this trend expected to continue into 2025 and 2026. The average annual insurance premium for Chicago condos is reported to be around $890.

Buildings that cannot absorb the increase in insurance premiums fully may resort to special assessments. There have been reports of charges ranging from $5,000 to over $50,000 per unit when roof, masonry, elevator, or mechanical work overlaps. High-rises, with their complex systems, may face larger assessments, while vintage buildings, having lower management fees, may have thinner reserve funds, making assessments feel sudden. Whichever option you choose, there are pros and cons to consider.

Illinois does not impose a cap on special assessments, but board meetings require written notice 10 to 30 days in advance, and if the total assessments for the current year exceed 115 percent of the previous year, 20 percent of unit owners can contest it with their signatures. It's also good to know that two-thirds of unit owner consent is needed for assessments outside the budget for common area changes.

Regardless of which type you choose, there are common items to verify before signing a contract.

• Recent three years of insurance renewal history and increases
• Reserve study results and funding rates
• Recent or planned special assessments
• Percentage of delinquent units and litigation history
• Percentage of rental units and whether they meet Fannie Mae's warrantable criteria

Buildings with more than 15 percent delinquent units or ongoing litigation may be classified as non-warrantable under Fannie Mae's criteria, which could lead to unfavorable loan conditions, a risk signal that applies to both types.

Low management fees are not always advantageous, nor are high fees always safe. To see the real picture, one must also consider the reserve funds and insurance conditions behind them. From an investment perspective, Chicago has a strong rental demand, particularly in downtown and the North Side, resulting in relatively low vacancy burdens. However, buildings poorly managed by their associations may offset several years of rental income with a single special assessment, making it safer to evaluate the management history when comparing the two types. This article is not investment or legal advice, and it is recommended to review financial statements and insurance renewal history with a professional before making any contracts.