Is it too late to start looking for a 2 flat in Chicago as of July 2025?

With housing costs squeezing budgets and rents continuing to climb, many Chicago buyers are searching for options that offer both stability and long-term value. For some, the answer may lie in an enduring staple of the city’s real estate landscape: the two-flat.

As of July 2025, it is not too late to begin searching for a two-flat in Chicago. The market remains active, and for buyers who are prepared and ready to move, opportunities still exist. While housing inventory has been limited in recent years, many expect an increase in listings this year, potentially easing competition and expanding the range of choices available.

Rising rents and consistent demand have kept multi-family properties, including two-flats, firmly in focus for both investors and owner-occupants. Despite price growth in some neighborhoods, Chicago remains more affordable than many major coastal cities, and multi-unit homes continue to offer a compelling combination of equity-building and rental income.

Buyers willing to engage directly with for-sale-by-owner sellers may find the process refreshingly straightforward. In many cases, this approach can streamline communication and avoid unnecessary fees. Partnering with a trusted real estate attorney can help ensure a smooth and legally sound transaction from start to finish.

The key is to stay informed, recognize a good opportunity when it arises, and act with confidence in a market that still offers solid long-term potential.