Chicago Judge Raymond Myles, 66 (pictured), was shot dead outside his home on the city's south side early Monday morning

A 66-year-old Chicago judge was shot to death outside of his home on the South Side early Monday morning, in what police say may have been an attempted robbery.

Neighbors said they heard a woman's screams coming from the home of Associate Judge Raymond Myles just before 5am.

A 52-year-old woman - described as a 'close associate' of the judge - was shot in the leg when she left the home and encountered an armed man.

Neighbors said Myles and the unidentified woman often left early in the morning to work out at a gym.

Myles heard the commotion and came outside where he was shot at least four times. He died after being transported to Advocate Medical Center.

His female friend was last reported in serious condition at the same hospital, and has underwent surgery. She is expected to survive.

No one has been arrested in connection to the shooting so far. The suspect has been described as a black man.

Police say the shooting matches 'some patterns of robberies' in the area. However, they say nothing appears to have been taken from the property.

Authorities gather outside Myles' home on the South Side of Chicago Monday morning

A 52-year-old woman was also shot in the leg and is in serious condition. No arrests have been made

Myles' death coincides with a frightening rise in murders in the Windy City. Last year, the murder rate surpassed 750 homicides for the first time since the 1990s, and it's on track to have a similarly deadly year in 2017, with more than 150 reported already.

One neighbor, who asked not to be identified, described the chaos to the Chicago Tribune.

'I heard maybe six shots. The shots woke me up, and the screaming of the woman woke me up. She was screaming, "Don't kill him, don't kill him!"' the neighbor recalled.

The judge and the woman who was injured usually leave early in the morning to go work out, according to the neighbor.

Above is Judge Myles' home. Neighbors say they were woken up to gunshots just before 5am. The victims' bodies were found in the back of the property, where the garage is

The neighbor also said that he believes the shooting may have been caught on surveillance camera, since the judge planned to install some on his property.

'I knew him well,' the neighbor said. 'Great guy, great neighbor. He looked after the neighborhood. Any mischief in the neighborhood, he was investigating. He was always at the block clubs. He never talked about being a judge. He was just Ray.'

Chicago Police Department spokesman Anthony Guglielmi called the shooting a 'senseless murder'.

In a statement, Cook County Chief Judge Timothy Evans said he was 'deeply saddened' by the news.

'I know you join me in sending our condolences to his family and colleagues in the Criminal Division,' Evans said.

Myles was an associate judge in the court's criminal division, and handled several high-profile cases in his career.

The two suspects arrested for the 1993 Brown's Chicken massacre, appeared before Myles shortly after their arrest in 2002 for the mass murder.

He also ordered William Balfour held without bond after he was arrested for the 2008 murders of three relatives of singer Jennifer Hudson.

Just two years ago, Myles was also attacked by a man in a minor traffic collision.

Myles was trying to park when he was struck by another vehicle. The driver of the other car punched him in the face when he tried to take pictures of the damage to his car.

Myles had to be taken to the hospital for a fractured nose, chipped tooth and injuries that later required reconstructive surgery.

Ten months later, 22-year-old Deandre Hudson was arrested for the attack and charged with aggravated battery causing great bodily harm to someone over the age of 60.