1421-1427 N. Milwaukee Avenue

Wicker Park sits on Chicago’s Northwest Side, with tree-lined residential blocks surrounding the lively Milwaukee Avenue corridor. Its four-season climate brings warm summers, cold winters, and plenty of changing weather for exploring the neighborhood. The landmark Flatiron Arts Building reflects the area’s creative history, while Wicker Park itself offers lawns, paths, a playground, and space to walk dogs. Cafés, restaurants, and bars cluster along Milwaukee, Damen, and Division, alongside boutiques, vintage shops, and independent galleries. The 606 trail is nearby for walking and biking, and the neighborhood’s music venues and late-night spots add to its arts and nightlife scene. The Blue Line’s Damen station and frequent buses connect Wicker Park with downtown and other parts of Chicago; cycling and walking are also practical ways to get around. For the Wicker Park neighborhood, the median rent is $3,100 per month, with a typical range of $1,075 to $19,941.