Top 10 Most Expensive Streets in Austin, Chicago, IL

Lincoln Avenue is the 1st most expensive street in Chicago. It has condos, townhouses, multi-units, and land built from 1911 to 2025, ranging in price from $270,000 to $1,650,000. It is home to the Lincoln Crossing, Plaza Vista, The Pointe, Lincoln Park Terrace, 5300 N. Lincoln, Delta On Lincoln, Ivy Lane, 2626 N. Lincoln, The Chelsea, 5067 N Lincoln, 4050 N. Lincoln, Palace Lofts, 5003 N. Lincoln, 4114 N. Lincoln, 3151 N. Lincoln, Walpole Point, 2936 N. Lincoln, 4152 N. Lincoln, Lincoln Square Ravenswood, Vinery Lofts, Emerald City, Lincoln Point, 2843 N. Lincoln, Lincoln Theater Lofts, The Chaville, 4949 N. Lincoln, 4118 N. Lincoln, 3118 N. Lincoln, Seminary Court, 5061 N. Lincoln Avenue North, 2474 N. Lincoln, 2461 N. Lincoln, 3530 N. Lincoln, 3808 N. Lincoln, The Lincoln, Atrium at Lincoln, 3057 N. Lincoln, 3325 N. Lincoln, 2039 N. Lincoln, 2140 N. Lincoln, Bowmanville, and 2800 N. Lincoln Avenue subdivisions.

Grace Street is the 2nd most expensive street in Chicago. It has condos, townhouses, single-family homes, and multi-units built from 1903 to 2025, ranging in price from $200,000 to $2,599,000. It is home to the Park View East, 1714 W. Grace, 1622 W. Grace, 1724 W. Grace, Lofts at 1800, 841 W. Grace, 1137 W. Grace, Portage Park Condos, and 1151 W. Grace subdivisions.

Junior Terrace is the 3rd most expensive street in Chicago. It has condos, co-ops, and single-family homes built from 1910 to 1989, ranging in price from $289,000 to $1,726,250.

Randolph Street is the 4th most expensive street in Chicago. It has condos, co-ops, and land built from 2007 to 2009, ranging in price from $33,000 to $3,530,000. It is home to the 340 on the Park, Outer Drive East, The Buckingham, Buckingham Residences, RD 659 Condos, Joffrey Tower, City View Tower, and 626 W. Randolph St. subdivisions.

Montana Street is the 5th most expensive street in Chicago. It has condos, single-family homes, townhouses, land, and multi-units ranging in price from $98,000 to $1,852,000. It is home to the 939 West Montana, 936 W. Montana, Kelvyn Park, and 5101 W. Montana subdivisions.

Bosworth Avenue is the 6th most expensive street in Chicago. It has condos, townhouses, single-family homes, multi-units, and land built from 1890 to 2025, ranging in price from $135,000 to $3,850,000. It is home to the Bosworth Place, 1307 N. Bosworth, Altgeld Commons, 3701 N. Bosworth, 1501 W. Bosworth, 1315 N. Bosworth, Southport Corridor, 3607 N. Bosworth, 2650 N. Bosworth Avenue, 1232 N. Bosworth, 1228 N. Bosworth, and 1238 N. Bosworth subdivisions.

Oak Street is the 7th most expensive street in Chicago. It has condos and townhouses built from 1995 to 2015, ranging in price from $435,000 to $3,200,000. It is home to the 30 W. Oak, Oak Club Condos, and Oak Street Terrace subdivisions.

Wolcott Avenue is the 8th most expensive street in Chicago. It has single-family homes, condos, townhouses, co-ops, multi-units, and land built from 1898 to 2026, ranging in price from $25,000 to $4,350,000. It is home to the 4110 N. Wolcott, 3910 N. Wolcott, 2743 N. Wolcott, 6969 N. Wolcott, 3420 N. Wolcott, 925 N. Wolcott, Brownstone on Wolcott, 4446 N. Wolcott, 2736 N. Wolcott, Landmark Village, Signature Lofts, Wolcott Village, 4645 N. Wolcott, 5013 N. Wolcott, Wolcott Court, The Linn, 4055 N. Wolcott, 5046 N. Wolcott, 5011 N. Wolcott, Wolcott Square, 1615 N. Wolcott, 1222 N. Wolcott, 6105 N. Wolcott, 2770 N. Wolcott, The Vine Condominiums, 4708 N. Wolcott, 4202 N. Wolcott, Granville Terrace, Castle Manor, 7301 N. Wolcott, and 3400 S. Wolcott subdivisions.

Fairbanks Court is the 9th most expensive street in Chicago. It has condos and land built from 2003 to 2008, ranging in price from $30,000 to $1,250,000. It is home to the 600 North Fairbanks subdivision.

Prairie Avenue is the 10th most expensive street in Chicago. It has condos, townhouses, single-family homes, land, and multi-units built from 1893 to 2025, ranging in price from $20,000 to $1,530,000. It is home to the One Museum Park West, Prairie House, Museum Park Towers, Prairie Pointe, Museum Park Tower IV, 4543 S. Prairie, One Museum Park, 4829 S. Prairie, 4854 S. Prairie, 4858 S. Prairie, 1717 S. Prairie, Prairie Place, Prairie District Homes, 1600 Museum Park, 4109 S. Prairie, Prairie Court, Prairie District Tower, Park Manor, Museum Park Place, 3541 S. Prairie, 4817 S. Prairie, and Rosemoor subdivisions.