This photograph organizes the city into horizontal layers, starting with the water in the foreground and moving up through a harbor to the dense skyline. The eye begins at the moving boat in the lower center and moves upward toward the large, white lettering that spans the top half of the frame. These sans-serif letters are placed directly over the sky and the highest points of the skyscrapers, creating a flat layer over the deep view of the buildings. The tallest structures anchor the far left and right sides, framing a middle section filled with various rectangular and pointed rooflines.

A thin, dark line of trees and a cluster of many narrow masts sit between the water and the base of the buildings, separating the natural and man-made elements. The monochrome tones highlight the contrast between the solid, dark shapes of the skyscrapers and the bright, clear sky behind the text. While the artist notes the city's location on Lake Michigan, the image focuses on the physical density of the cityscape and how the bold name of the city sits across the upper portion of the architecture.

This work belongs to a series that includes another version titled CHICAGO Skyline | Text, continuing the artist's use of typography within classical cityscapes.