It happened around 9:30 p.m. on the Roosevelt Boulevard near Rising Sun Avenue.
According to Philadelphia Police Chief Inspector Scott Small, a 38-year-old man and 24-year-old woman were on a motorcycle when they collided with a 24-year-old woman on another bike.
All three victims were reportedly traveling together with a group of other motoryclists.
The collision caused one of the motorcycles to crash into the back of a parked and unattended tractor-trailer.
Police described the crash as very violent, adding that some of the victims suffered very traumatic injuries.
Small said the impact sheared off the 38-year-old man's leg.
Police found the man and 24-year-old woman unresponsive at the scene. They were both taken to Einstein Medical Center in critical condition.
The 30-year-old woman was found conscious and taken to Temple University Hospital. She was suffering from numerous bumps and bruises but is expected to survive her injuries.
Small said debris from the motorcycles, sneakers from the victims and bone fragments were found at the scene.
"The debris spanned about 300 feet north from Rising Sun Avenue," said Small.
According to authorities, another vehicle may have caused the riders to swerve into each other.
"We don't believe that vehicle struck the motorcycle. We don't believe that vehicle was even involved in the accident, but may have caused these two motorcycles to lose control and strike each other," said Small.
Police said the license plates on both bikes fell off in the crash, but were recovered by officers.
Investigators are interviewing witnesses and gathering nearby surveillance videos in hopes of finding more clues into what caused the crash.