Near West Side

What they share is proximity. This community area sits directly west of the Loop, close enough that a large share of residents walk to work. That is unusual in Chicago and it is the foundation of everything else here.

The biggest thing on the horizon is 725 W Randolph in Fulton Market: a 45-story, roughly 700-foot, 968,000 square foot office tower from Related Midwest designed by Kohn Pedersen Fox. Sidley Austin will take over half the office space, relocating from 1 S Dearborn when its lease expires in 2030. Ground is expected to break in 2027 with an opening in 2030. The project pivoted from an earlier mixed-use residential and hotel proposal to office only.

I mention it because an anchor tenant of that size changes the daytime population, and daytime population is what pulls retail and then residential. It also means several years of construction on the north end.

On buildings, the county's records put the two-to-four unit median here at about $681,000 in 2025, up roughly 86% since 2013. But look at the shape rather than the endpoints: the run happened between 2018 and 2021, and the last four years have been essentially flat, moving between $650,000 and $691,000. That is a market that repriced and then paused.

Rents tell the same story. Two-bedrooms at $3,950 and three-bedrooms at $5,300 are both roughly flat year over year, and one-bedrooms are up only 2%. Heavy new apartment supply is the likeliest explanation, and it is why I would be careful underwriting rent growth here that the last twelve months do not support.

Where I would look: the older stock in University Village and around Tri-Taylor, where the purchase price never joined the West Loop run and the rents still clear. The West Loop itself is a fine place to own and a hard place to buy well right now.