Chicago Best Places of Interest
- Paul H. Douglas Nature Sanctuary
- Pegasus Players
- Peggy Notebaert Nature Museum
- Petrillo Music Shell
- pH Comedy Theater
- Picasso Statue ("Untitled")
- Pilgrim Baptist Church
- Pleasant Home
- Polish Museum of America
- Porchlight Music Theatre
- Prairie Avenue Historic District
- Printers Row
- Pritzker Military Museum & Library
- Profiles Theatre
- Provision Theater
- Pump It Up Party Zone
- Puppet Parlor
- Reading Cones - Grant Park
- Redmoon Theater
- Red Orchid Theatre
- Reliance Building (Hotel Burnham)
- Remy Bumppo Theatre Company
- Renaissance Society
- Richard H. Driehaus Museum
- Richard J. Daley
- Riverdale Marina
- River East Art Center
- Riviera Theatre
- Robie House
- RobotCity Workshop