Philadelphia has a limited system of expressways, partly due to the "freeway revolts" of the 1960s and 1970s. Several planned crosstown freeways were cancelled due to local opposition, particularly from neighborhoods which would have been displaced by the freeways.

One of the proposed freeways was Interstate 695, which would have run along South Street from the Delaware waterfront to the Schuylkill River as the "Crosstown Expresway", and continue through Southwest Philadelphia to Interstate 95 as the "Cobbs Creek Expressway". Although the Roosevelt Boulevard was proposed to be fully converted to an expressway, only the portion between Broad Street and the Schuylkill Expressway is built to freeway standards.

The main expressways of Philadelphia are the Delaware Expressway (I-95), which travels along the Delaware River, and the Schuylkill Expressway (I-76), paralleling the Schuylkill River for most of its route. Other expressways are the Vine Street Expressway (I-676), running between the Schuylkill Expressway and Delaware Expressway through downtown Philadelphia, and the Roosevelt Expressway (US 1), a freeway portion of the Roosevelt Boulevard.