Top 10 Most Expensive Streets in Loop, Chicago, IL

Castlewood Terrace is the 1st most expensive street in Chicago. It has single-family homes built from 1909 to 1990, with an average sale price of $2,650,000.

Fern Court is the 2nd most expensive street in Chicago. It has single-family homes and multi-units built from 1903 to 1905, with an average sale price of $2,325,000.

Wacker Drive is the 3rd most expensive street in Chicago. It has condos built from 2020 to 2021, ranging in price from $930,000 to $6,475,000. It is home to the Vista Residences subdivision.

Oak Street is the 4th most expensive street in Chicago. It has condos and townhouses built from 1995 to 2007, ranging in price from $435,000 to $5,250,000. It is home to the 30 W. Oak, Oak Club Condos, and Oak Street Terrace subdivisions.

Marion Court is the 5th most expensive street in Chicago. It has single-family homes built from 1999 to 2024, ranging in price from $1,550,000 to $2,375,000.

Howe Street is the 6th most expensive street in Chicago. It has condos and single-family homes built from 1904 to 2025, ranging in price from $250,100 to $4,400,000. It is home to the 2020 N. Howe subdivision.

Dayton Street is the 7th most expensive street in Chicago. It has condos, single-family homes, townhouses, and land built from 1910 to 2019, ranging in price from $505,000 to $3,100,000. It is home to the 1651 N. Dayton, 4324 N. Dayton, 1911 N. Dayton, and City Homes on Dayton subdivisions.

Maud Avenue is the 8th most expensive street in Chicago. It has townhouses, single-family homes, and condos ranging in price from $630,000 to $2,650,000. It is home to the 1920 N. Maud Ave. and Maud Court subdivisions.

Menomonee Street is the 9th most expensive street in Chicago. It has single-family homes and townhouses built from 1875 to 2019, ranging in price from $810,000 to $2,275,000.

Grant Place is the 10th most expensive street in Chicago. It has single-family homes, condos, and land built from 1988 to 2025, ranging in price from $575,000 to $4,200,000. It is home to the 432 W. Grant, 455 S. Grant Pl., and The Portals subdivisions.