The shooting occurred at about 1:30 a.m. in the 3100-block of North Clark Street, police said.
Video shows a large crowd was on the street when someone began shooting. The victims were all outside but not standing together, police said.
A 46-year-old woman was shot in the abdomen and transported to Illinois Masonic Medical Center in critical condition, police said.
25 shot, 5 fatally, in Chicago weekend violence
A 30-year-old man was shot in the knee and transported to Illinois Masonic Medical Center in good condition.
3 stabbed in fight in Lakeview East, Chicago police say
A 37-year-old man was shot in the leg and was transported to Northwestern Memorial Hospital in good condition.
Many people were still out celebrating at the time of the shooting after the Pride Parade Sunday.
Alderman Tom Tunney requested extra police patrols over concerns of high turnout for the Pride Parade's return.
"It's sad, but you know the reality is when you have this type of crowd and this many people and people that have been drinking and carrying on so to speak, there's a lot of vulnerability and there's a lot of police officers who need to be out here," Alderman Tunney said. "And that's what I have been asking for and the mayor agreed, as did the superintendent and so I'm thankful and the community is thankful."
A gun was recovered from the scene.
Area Three detectives are investigating the shooting. No one is in custody.