Top 10 Most Expensive Streets in Uptown, 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 built in 1903, with an average sale price of $2,325,000.

Wacker Drive is the 3rd most expensive street in Chicago. It has condos ranging in price from $930,000 to $6,537,000. It is home to the Vista Residences subdivision.

Race Street is the 4th most expensive street in Chicago. It has single-family homes built in 2020, with an average sale price of $2,210,000.

Benton Place is the 5th most expensive street in Chicago. It has townhouses built in 2009, with an average sale price of $2,000,000.

Marion Court is the 6th 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 7th most expensive street in Chicago. It has condos and single-family homes built from 1904 to 2024, ranging in price from $250,100 to $4,400,000. It is home to the 2020 N. Howe and 1964 N. Howe subdivisions.

Oak Street is the 8th most expensive street in Chicago. It has condos and townhouses built from 1995 to 2015, 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.

Maud Avenue is the 9th most expensive street in Chicago. It has townhouses and single-family homes built from 1989 to 2024, ranging in price from $630,000 to $2,650,000. It is home to the 1920 N. Maud Ave. and Maud Court subdivisions.

Ainslie Avenue is the 10th most expensive street in Chicago. It has single-family homes and multi-units built from 1931 to 2019, ranging in price from $827,000 to $2,300,000.