Top 10 Most Expensive Streets in Chicago

Clifton Street is the 1st most expensive street in Chicago, with condos/townhomes and single family homes built from 2004 to 2012, and averaging $3,275,000. It is home to the 2002 N. Clifton and 3736 N. Clifton subdivisions.

Wacker Drive is the 2nd most expensive street in Chicago, with condos/townhomes homes built from 2020 to 2021, and ranging in price from $930,000 to $7,000,000. It is home to the Vista Residences subdivision.

Fern Court is the 3rd most expensive street in Chicago, with condos/townhomes and single family homes built from 1873 to 1973, and averaging $2,325,000.

Ainslie Avenue is the 4th most expensive street in Chicago, with condos/townhomes and single family homes built from 1920 to 2019, and averaging $2,300,000. It is home to the 1603 W. Ainslie, 3515 W. Ainslie, 846 W. Ainslie, and Harding Court Condos subdivisions.

Race Street is the 5th most expensive street in Chicago, with single family and condos/townhomes homes built in 2020, and averaging $2,210,000.

Benton Place is the 6th most expensive street in Chicago, with condos/townhomes homes built from 2008 to 2009, and averaging $2,000,000.

Caton Street is the 7th most expensive street in Chicago, with condos/townhomes and single family homes built from 1891 to 1920, and ranging in price from $1,575,000 to $2,370,000.

Castlewood Terrace is the 8th most expensive street in Chicago, with single family homes built from 1898 to 1990, and ranging in price from $685,000 to $2,775,000.

Howe Street is the 9th most expensive street in Chicago, with condos/townhomes and single family homes and ranging in price from $250,100 to $7,200,000. It is home to the 1929 N. Howe, 1962 N. Howe, 1964 N. Howe, 2020 N. Howe, 635 W. Armitage, and Old Town Village subdivisions.

Dayton Street is the 10th most expensive street in Chicago, with single family and condos/townhomes homes built from 1884 to 2025, and ranging in price from $370,000 to $4,750,000. It is home to the 1651 N. Dayton, 1819 N. Dayton, 1827 N. Dayton, 1911 N. Dayton, 2055 N. Dayton, 4324 N. Dayton, Buena Park, City Homes on Dayton, and Willow Dayton subdivisions.