Top 10 Most Expensive Streets in Bucktown, Chicago, IL

Dayton Avenue is the 1st most expensive street in Chicago. It has single-family homes built from 2012 to 2026, with an average sale price of $4,304,300.

Clifton Street is the 2nd most expensive street in Chicago. It has single-family homes built in 2008, with an average sale price of $3,275,000.

Dickens Street is the 3rd most expensive street in Chicago. It has single-family homes ranging in price from $1,500,000 to $4,600,000.

Orchard Avenue is the 4th most expensive street in Chicago. It has single-family homes built in 1890, with an average sale price of $2,737,500.

Magnolia Street is the 5th most expensive street in Chicago. It has single-family homes and condos built from 1875 to 2025, ranging in price from $1,310,000 to $3,925,000. It is home to the Headley School Lofts subdivision.

Wacker Drive is the 6th most expensive street in Chicago. It has condos ranging in price from $800,000 to $6,475,000. It is home to the Vista Residences subdivision.

Caton Street is the 7th most expensive street in Chicago. It has single-family homes built from 1888 to 1891, with an average sale price of $2,370,000.

Howe Street is the 8th most expensive street in Chicago. It has single-family homes, condos, and townhouses built from 1904 to 2025, ranging in price from $325,000 to $4,747,956. It is home to the 2020 N. Howe and 1964 N. Howe subdivisions.

Castlewood Terrace is the 9th most expensive street in Chicago. It has single-family homes built from 1909 to 1990, ranging in price from $1,399,000 to $2,650,000.

Janssen Street is the 10th most expensive street in Chicago. It has single-family homes and condos built in 2026, ranging in price from $490,000 to $4,450,000. It is home to the 2401 N. Janssen subdivision.