Top 10 Most Expensive Streets in Near South Side, 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.

Vernon Park Place is the 3rd most expensive street in Chicago. It has townhouses and condos built from 1988 to 2003, ranging in price from $375,000 to $776,000. It is home to the Tuscany Club Villas and Vernon Park Townhomes subdivisions.

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.

Huron Street is the 5th most expensive street in Chicago. It has condos, single-family homes, townhouses, land, and multi-units built from 1891 to 2026, ranging in price from $16,000 to $4,500,000. It is home to the 451 Huron Condos, The Pinnacle, Huron Pointe, Huron Street Lofts, Chicago Place, 30 East Huron, Hermitage, 30 E. Huron, Tuxedo Park, 1322 W. Huron, 33 W. Huron, Montreux Condos, River North Commons, 950 W. Huron, Noble Square, 1508 W. Huron, City Club, 400 W. Huron, 2330 W. Huron, 945 W. Huron, 56 W. Huron, 351 W. Huron, 2258 W. Huron, River West Courts, and 1748 W. Huron subdivisions.

14th Street is the 6th most expensive street in Chicago. It has condos, land, and multi-units built from 1910 to 2008, ranging in price from $238,500 to $770,000. It is home to the 1400 Museum Park, Lawndale, and 757 W. 14th subdivisions.

Bosworth Avenue is the 7th 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 8th 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 9th 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.

Monroe Street is the 10th most expensive street in Chicago. It has condos, townhouses, land, single-family homes, and multi-units ranging in price from $12,000 to $3,200,000. It is home to the The Flats on Monroe, 1228 W. Monroe, 955 W. Monroe, Park 1500 Lofts, 950 West Monroe, Monroe Manor, The Metro, 1526 W. Monroe, Park Monroe, 2212 W. Monroe, Metropolis Condominiums, Carmichael Place, The Legacy at Millennium Park, 1148 W. Monroe, 1234 W. Monroe, Block Y, 2136 W. Monroe St., Mentor Building, 1000 W. Monroe, Chelsea Townhomes, 1244 W. Monroe, Westhaven Park, 1400 W. Monroe, and Metropolitan Place subdivisions.