The incident occurred at about 4:53 a.m. in the 100-block of East Walton Street along the Magnificent Mile downtown.
Police said a group of suspects crashed a pick-up truck into the Louis Vuitton store.
Cellphone video from a witness captured the moment thieves rammed a vehicle into the luxury store.
The video then shows a group of people dressed in dark clothing run into the store and then run out with stolen items.
The people are then seen getting into other vehicles that were either parked nearby or that pull up. All the cars then speed away.
Police said one of the getaway vehicles, a Kia Stinger, drove south on Michigan Avenue, where it crashed with a Honda CR-V at Ohio Street.
The driver of the Honda, a man in his 40s who was not involved in the burglary, was taken to Northwestern Memorial Hospital, where he died, police said.
Five suspects from the Kia were taken into custody and taken to hospitals with non-life-threatening injuries, police said.
"They hit the car that was coming this way, that was coming the other way, and they just smashed into each other," witness Harry Lipman said.
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Police said another getaway vehicle drove south on DuSable Lake Shore Drive when it lost control near Roosevelt Road, and four suspects fled on foot. Two suspects were taken into custody, and two others escaped, police said.
No injuries were reported, and proceeds from the burglary were found in the vehicle.
The commotion woke up many of those staying at nearby hotels.
"I happened to wake up and say all the flashing lights. So that's what alerted me to the fact that there was a problem down here," Lipman said.
This is the second break-in in the Gold Coast over the last few weeks.
"This is the second major incident in a row where there was a robbery on Michigan Avenue that involved violence," 2nd Ward Ald. Brian Hopkins said. "We're going to be installing security bollards in the coming weeks. That was planned even before this incident happened, but we shouldn't have to resort to those tactics. We're trying to recover the economy of Michigan Avenue. We've had record vacancy rates in recent years. They are finally starting to inch down. This doesn't help."
A Rolex store was broken into in broad daylight less than a week ago.
Two and a half weeks ago, a crew of up to 10 thieves struck the Louis Vuitton section inside the nearby Nordstrom.
"These are not victimless crimes; these are dangerous crimes. And the people who continue to perpetrate them need to be prosecuted and jailed for lengthy sentences," Hopkins said. "We are done tolerating it."
Hopkins said prosecuting those perpetrating these crimes is imperative, but so is going after the organized criminal groups behind them.
"It's time for judges to get tough, and it's time for sentences to get tough. People who do this need to go to jail, and they need to be held there for a long period of time so they can't do it again," Hopkins said.
Thursday afternoon, those walking by were still drawn to the crime scene.
Hopkins also said this incident is being escalated to a multi-agency retail theft task force that involves branches of the federal government and the U.S. Justice Department. So far, he says police have recovered over $180,000 in stolen merchandise.
Area detectives and the Major Accident Investigation Unit are investigating.
Charges are pending, as is the identity of the man killed.
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