As 2026 comes to a close, Chicago homebuyers have a few important things to consider before making their next move. Whether you’re actively searching or planning to buy a home in Chicago in 2027, now is a good time to get familiar with the market.

Understand Where the Chicago Housing Market Stands

According to Realtor.com, active listings in Chicago decreased 5.3% year-over-year in September 2026, while the median listing price increased 4.6%. Inventory remains an important consideration, particularly in desirable North Side neighborhoods.

While the winter months can bring less competition, they can also mean fewer homes to choose from.

Look Beyond Your Mortgage Payment

Property taxes, homeowners insurance, utilities, and maintenance all contribute to the true cost of homeownership. If you’re considering a Chicago condo, you’ll also want to factor in monthly association fees and potential special assessments.

Understanding these expenses early can help you establish a realistic budget.

Get Your Financing in Order

Mortgage rates may change, but waiting for the perfect rate isn’t always the best strategy. Speak with a trusted lender about your purchasing power, loan options, and what a comfortable monthly payment looks like for you.

Start Planning for 2027

Even if you’re not ready to purchase before December, there’s value in starting your search now. Research Chicago neighborhoods, explore available properties, and connect with an experienced local real estate team.

At The O’Connor Group, we help buyers understand their options and make informed decisions based on their goals, not just the calendar.