The first carjacking occurred in the 2600-block of West Fitch Avenue at about 8:30 p.m. Police said a 31-year-old man was parked in a red Land Rover when two suspects approached, opened the door, took out a handgun and demanded the car.
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The man complied with the carjackers, who fled south on Rockwell Street and went on to commit two robberies in the Loop, police said.
"I was there on the sidewalk talking on the phone and then all of a sudden someone jumps from the car," said the victim of one of those robberies, who asked not to be identified.
The victim was on Michigan and Adams at 10 p.m. when he said a man with a gun demanded his Canada Goose jacket.
"He took me from the back, like, pointing to me with a gun and covered mask, and he was asking me, like, pull your jacket off, pull your jacket off," the victim said.
Police said the second robbery happened about 10 minutes later in the South Loop, on 13th Street near Indiana. Police said two male robbers, between 16 and 26 years old, approached a 26-year-old man and 41-year-old man, and demanded their property.
The victims gave them their luxury watches, wallets, cash, cell phones and coats, police said.
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One of the robbers was armed with a handgun, police said. They then fled in a waiting red Range Rover Sport that fled west on 13th Street and south on Michigan Avenue.
In each incident, the victims were unharmed.
Residents of the area said they know no area of the city is immune or safe from crime.
"You can't avoid it, you just have to pay very close attention to your surroundings and use your instincts," said Marica Hawthorne.
A second carjacking occurred in the Gold Coast as a man and woman were forced out of a Porsche at gunpoint.
The victims were about to park their car in the 1500-block of North Dearborn Street at about 9:10 p.m. when police said two men in dark clothing approached.
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One of the men was armed and demanded the keys to the car. The victims complied and one suspect fled in the victim's Porsche and the other fled in a maroon vehicle northbound in an alley, police said.
A third carjacking involved a black Jeep Cherokee whose occupants then went on to commit at least one robbery, police said.
In the Gold Coast, many people who live and work in the area are surprised.
"It's definitely very frightening and unsettling, especially for this area," said Rachiel Kennen. "I'm really glad to know that the family is alright."
"It's terrifying, you know," said resident Joe Spelde. "We're living on the same street we have the same type of garage so if we're pulling in at night now that's something we have to consider now."
Area Central detectives are investigating and said three different groups committed the carjackings. No one is in custody.