The Great Chicago Fire lasted for almost three days and affected a territory about 4 miles (6.5 km) in length by an average of two-thirds of a mile (1 km) in width (burnt district). The fire destroyed about 18,000 mostly wood-framed buildings. Soon after the fire, rebuilding began in earnest, and about 100 years after the fire, the world's tallest building was constructed in the burnt district. Many of the buildings that were constructed in the burnt district during the period of 1871 to 1930, or approximately 60 years after the fire had brick masonry exterior walls. Several of these buildings utilized innovative, exciting, and aesthetically pleasing applications of brick masonry wall systems. During the period of 1930 to 2017, or approximately 60 to 150 years after the fire, no significant building with innovative, exciting, and aesthetically pleasing applications of brick masonry wall systems was constructed in the burnt district. This condition led the author to consider what eventually became the title of this paper: Brick Masonry in Chicago: Crisis in Aesthetics? Based upon the evaluation of buildings that were constructed with brick masonry exterior walls in the burnt district from 1871 to 2017, or approximately 150 years subsequent to the fire, it is the author's opinion that there is an aesthetic crisis in these buildings and that improvements in the aesthetics should be considered. Recommendations to improve the aesthetics of buildings with brick masonry in exterior wall systems are presented in this paper for review and consideration by interested parties. The results of this evaluation are pertinent to buildings constructed in the burnt district after the fire and may not apply to buildings constructed with brick masonry exterior walls elsewhere during this same time period.