Updated 1/25/17: I was only looking at buildings with a single PIN until someone asked about the Merchandise Mart. It has two PINs and the combined value puts it at #2. I’ve adjusted the list.
With our property taxes database we know which properties get the highest property tax bills from the most by the Cook County Treasurer.
I hope you can guess the building with the highest property tax bill in 2015. (It’s not in this photo.)

It’s the Sears Tower at 233 S Wacker Dr. Its bill in 2015 was $26,570,654.23.
Can you guess the property with the next-highest bill? The bill is nearly 10 million less than the Willis Tower, at $17,729,040.54.
It’s the Merchandise Mart at 222 W Merchandise Mart Plz. The building goes by two PINs which is why it didn’t appear in this list at first.
How about the third property?
It’s the Aon Center at 200 E Randolph St, where the bill was $16,418,435.28.
Here’s the rest of Chicago’s top 10 (er, 11)
4. Blue Cross Blue Shield building at 300 E Randolph St; $16,386,783.42
5. Water Tower at 845 N Michigan Ave; $14,797,106.02
6. The building at 300 N LaSalle St; $13,465,861.78
7. Franklin Center, formerly known as the AT&T Corporate Center, and is the fifth tallest building in Chicago, at 227 W Monroe St; $13,356,591.53
8. Chase Tower, at 10 S Dearborn St; $13,278,373.73
9. Citadel Center, at 131 S Dearborn St; $12,861,241.93
10. Prudential Plaza, at 130 E Randolph St; $12,827,212.44
11. Three First National Plaza, at 70 W Madison St; $12,533,827.56
Based on this list I estimate that Illinois Center is the highest-density concentration of the city’s highest-value buildings. Four of the buildings on this list are in that development.