Law enforcement officials claim they found no evidence Paddock ever went to Chicago during the weekend of Lollapalooza, a music festival that attracts thousands of people.
The Blackstone Hotel, where Paddock made the reservations, overlooks the main stage and other stages at Grant Park where the music festival is held every year.
Paddock's booking of the hotel room, first reported by TMZ, comes as investigators, trying to determine a motive for the Las Vegas shooting, have been trying to track Paddock's movements in the days before he opened fire from the Mandalay Bay casino resort on Sunday night.
Police said Paddock spent decades acquiring weapons while living a 'secret life' and may have planned to escape the mass shooting alive.
Sheriff Joseph Lombardo today told reporters Paddock had 1600 rounds of ammunition and about 22kg of tannerite, an explosive commonly used in target shooting, in his car.
Sherrif Lombardo said, 'He meticulously planned the worst domestic attack in American history.'
Sheriff Lombardo also confirmed reports Paddock had rented a hotel room above another music festival just a week before the massacre.
Paddock booked a room at the Ogden hotel in downtown Las Vegas, which overlooks the site of the Life Is Beautiful festival.
Kiwi songstress Lorde, Chance the Rapper and UK rock band Muse were among the headliners at the September 22-24 festival.
'Was he doing pre-surveillance? We don't know yet,' Sheriff Lombardo said.
Sheriff Lombardo said police believe the 'disturbed and dangerous' Paddock planned to survive the shooting and escape, but did not reveal how.
His body was found by police when they breached his room, having apparently taken his own life. No suicide note was found in the room.
Paddocks Australian girlfriend, Marilou Danley, has returned to the US from the Philippines for questioning.