After crossing the railroads, the roadway curves in a northerly direction and becomes Hobbie Avenue before it enters Bradley.

[4] In Bradley, the road is known as Kinzie Avenue, and it continues due north, meeting a diamond interchange with Interstate 57 (I-57), then leaving the city.

It bends to the northeast, crosses the southern branch of Rock Creek, and passes through Manteno.

The route then continues due north through the remainder of Matteson, through the Southern Green Belt Forest Preserve, and into Country Club Hills.

Just north of I-57, IL 50 curves slightly to the northwest, leaves Country Club Hills and enters Oak Forest.

Here, the highway shares an interchange with I-294 (Tri-State Tollway), then continues due north into Oak Lawn.

The route re-enters Chicago a short distance later, meeting I-290 (Dwight D. Eisenhower Expressway) just north of the boundary.

The route then crosses the north branch of the Chicago River and intersects US 14 at Peterson Avenue.