Wallenda, a member of the Flying Wallenda tightrope-walking family, has success in his blood - but also failure. His great-grandfather Karl Wallenda fell to his death in a tightrope-walking stunt in Puerto Rico, aged 73. Ahead of the attempt he said: "Just looking at it is extremely intimidating."
WATCH FOOTAGE of Nik Wallenda's feat here
The daredevil's challenge started just after sunset, with the skyscrapers up and down the Chicago River lit up and sparkling.
He has now walked uphill at a 19-degree angle from the Marina City west tower to the top of a skyscraper on the other side of the river. Next, he'll walk blindfolded between the two Marina City towers.
If he slips, Nik will attempt to grab the wire as he falls, at which point rescuers will be able to slide down the wire to catch him. He says that he can cling on to the wire for as long as 30 minutes waiting for rescue.
Earlier he had spoken exclusively to MailOnline, revealing how he would be bound for death and failure without the unwavering support of his family.
The Wallenda clan have been tightrope walkers for generations - and witnessed Nik's great-grandfather Karl plummet to his death aged 73 while walking between two buildings in Puerto Rico.
Speaking a week ago from his home in Sarasota, Florida, he said: "It is key to my success to have that support. If I didn't have my mom and dad's support and my wife's support I wouldn't be able to make that walk."