Las Vegas gunman Stephen Paddock may have been planning to strike two months earlier at the Lollapalooza festival in Chicago.

Paddock, who slaughtered 58 people and injured 489, had allegedly booked two hotel rooms overlooking the Lollapalooza festival area during its duration in August.

Among the 400,000 attendees at this year's Lollapalooza was former President Barack Obama's oldest daughter Malia, and acts on stage included The Killers, Chance the Rapper, Muse and Charli XCX.

According to TMZ, Paddock made the booking using Expedia and insisted on a 'view room' which would overlook the festival. He also demanded he be notified in advance if such a room was unavailable.

He also researched possible locations in Boston online, according to multiple reports.

Anonymous officials said that Paddock looked for hotels near Fenway Park, where the Red Sox play and the Boston Center for the Arts. It was not known if the gunman went as far as making any reservations.

Mystery: Las Vegas gunman Stephen Paddock, 64, had booked himself into a hotel in Chicago, across the street from Grant Park where the Lollapalooza festival is held

Bird's view: Paddock had booked two rooms at the Blackstone Hotel, which overlooks the festival site, during Lollapalooza

Booking: Paddock had reserved two rooms at the Blackstone Hotel during the time of the event in August this year - two months before the Las Vegas massacre

Paddock's two rooms at the Blackstone Hotel, pictured, were booked from August 1st to 6th and from August 3rd to 6th - the time of the festival

Paddock had booked two rooms at the Blackstone Hotel in Chicago, across the street from Grant Park where Lollapalooza has been held since 2005.

Both rooms overlooked the festival area and Paddock insisted on a room with a view.

He would have had a similar position over the crowd as he had in Las Vegas during the Route 91 Harvest country music festival on Sunday.

Here's the startling bird's-eye view Stephen Paddock would've had from the Chicago hotel he booked just days before Lollapalooza kicked off. However, he never showed up for his reservation

According to TMZ, the Vegas killer demanded he be notified in advance if a view room was unavailable. In the end Paddock failed to turn up for the reservation.

'We are aware of the media reports and have been in communication with our federal partners. As you saw earlier this week the city conducts extensive public safety planning and training around major events, in close coordination with our law enforcement partners, to ensure public safety,' a spokesman for the Chicago Police Department said.

Lollapalooza was held from August 3 to 6 this year, and Paddock's two rooms were booked from August 1 to 6 and from August 3 to 6.

TMZ says Paddock, 64, never showed up for his bookings at the hotel.

Paddock is also believed to have planned on targeting another Vegas festival before Route 91.

Famous guests: Charli XCX and Liam Gallagher are seen during their performances at Lollapalooza 2017

Banks and Big Sean are seen during their respective performances

City festival: Lollapalooza has been held in Grant Park in Chicago since 2005

Paddock had also attempted to book rooms at the Ogden, a luxury condo tower that overlooked the Life is Beautiful open-air festival held in Las Vegas from September 22-24.

He requested specific suites at the Ogden and another unidentified hotel, but moved on when he discovered they were booked, an inside source told CBS on Wednesday.

Among the bands playing at Life is Beautiful were Chance the Rapper, Muse and Lorde - acts who all also played at Lollapalooza

This year the festival attracted 45,000 people per day.

Attendee: Malia Obama is seen dancing at the Lollapalooza festival 2017

Festival: The crowd at Lollapalooza is seen on the final day of the festival on August 6

An advertising feature that ran in the local papers before Life is Beautiful - attended by 45,000 per day this year - boasted that the Ogden was 'at the center' of the festival.

Life is Beautiful took place around five-and-a-half miles northeast of Sunday's massacre.

Meanwhile, Las Vegas police have revealed that Paddock, who killed himself after carrying out his brutal bloodbath, had originally hoped to survive his shooting and flee justice - and likely had an accomplice.

TIMELINE OF TERROR IN VEGAS: SUNDAY Country music star Jason Aldean was performing on stage at the Route 91 Harvest Music Festival when lone gunman Stephen Paddock, 64, opened fire on the 22,000 people gathered. 10:05pm: First shots fired by the suspect. This was seen on closed-circuit television from the concert venue. 10:12pm: First two officers arrive on the 31st floor and announce the gunfire is coming from directly above them. 10:15pm: The last shots are fired from the suspect per body cam worn camera. 10:17pm: The first two officers arrive on the 32nd floor. 10:18pm: Security officer tells the LVMPD officers he was shot and gives them the exact location of the suspect's room. 10:26-10:30pm: Eight additional officers arrived on the 32nd floor and began to move systematically down the hallway, clearing every room and looking for any injured people. They move this way because they no longer hear the gunfire of an active shooter situation. 10:55pm: Eight officers arrive in the stairwell at the opposite end of the hallway nearest to the suspect's room. 11:20pm: The first breach was set off and officers entered the room. They observed the suspect down on the ground and also saw a second door that could not be accessed from their position. 11:27pm: The second breach was set off allowing officers to access the second room. Officers quickly realized there was no one else in the rooms and announced over the radio that the suspect was down. MONDAY 2.13am Monday: Investigators said that they are looking for the 'roommate' of the shooter - Marilou Danley - and describe her as a person of interest. 6.30am Monday: Investigators say they have located the suspect's girlfriend and say that she is overseas and is no longer a person of interest. TUESDAY 2pm: Sheriff says Marilou Danley is a person of interest again, after report that Paddock wired $100,000 to an account in the Philippines a week before the attack, while she was in the country. Tuesday night: Danley arrives back in the U.S. from the Philippines. She is wheeled off her flight at Los Angeles International Airport in a wheelchair. WEDNESDAY Wednesday afternoon: FBI agents begin interviewing Danley . Advertisement

Young joy: A crowd of cheering young adults wait for a performance during Lollapalooza

Chilling: Paddock would have had a similar view of the Lollapalooza crowd as he had at the Mandalay Bay hotel (pictured) during the Route 91 Harvest country music festival on Sunday

Paddock had planned to escape the 32nd floor of the Mandalay Bay hotel after firing on the Route 91 Harvest country music festival, Las Vegas Sheriff Joseph Lombardo revealed in a press conference Wednesday.

Lombardo declined to reveal why he believed that Paddock had an exit planned, but said he was confident in the claim - and said that his scheme was so elaborate that he would have to be a 'super hero' to pull it off alone.

He said Paddock lived a 'secret life' and 'meticulously planned on the worst domestic attack in United States history.'

'Stephen Paddock is a man who spent decades acquiring weapons and ammo and lived a secret life, much of which will never be fully understood,' Lombardo said.

Candles are lit at a makeshift memorial for the 58 people killed in the massacre on Sunday

People run from the Route 91 Harvest country music festival after gunfire was heard