Paddock, 64, who launched a shooting massacre in Las Vegas, on Sunday murdering 58 people and injuring 515 had allegedly booked two hotel rooms overlooking the Lollapalooza festival in August.
The festival is popular with the children of the rich and famous – including former US President Barack Obama’s eldest daughter Malia.
At least 400,000 people attended Lollapalooza this year to watch acts including The Killers, Chance the rapper, Liam Gallagher and Charli XCX perform.
Paddock booked two rooms at the Blackstone Hotel in Chicago, located right across the street from Grant Park where the festival takes place, according to TMZ.
It would have put Paddock in a prime position to look down on the festival from the hotel – eerily similar to his position at the Mandalay Bay Hotel in Las Vegas.
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Lollapalooza was held from August 3 to 6 this year, and Paddock had booked the room from August 1 to 6 and August 3 to 6, according to the US site.
But law enforcement officials confirmed he never showed up to the hotel.
Paddock appeared to have booked other hotel rooms before his deadly mass shooting rampage in Las Vegas, according to police.
Bookings have been uncovered in Ogden a luxury condo tower that overlooks the Life is Beautiful festival in Las Vegas from September 22 to 24.
The first booking was made a full two months before he opened fire on a country music concert in Las Vegas from a 32nd-floor room of a hotel in the deadliest mass shooting in modern US history.
The revelations come as investigators are still trying to determine a motive for the Las Vegas shooting.
They are slowly piecing together his movements in the days before he caused panic and carnage at what was supposed to be a nice night out.
FBI Deputy Director Andrew McCabe said he was surprised Paddock had provided so few clues, and that it has made their probe extremely challenging.