In its early days, State Road was unpaved and known for having mud so deep it was jokingly said that it could suck down a horse and buggy.

[6] During the second half of the 20th century, State Street was eclipsed by Michigan Avenue's Magnificent Mile as a shopping district.

Anchored by Macy's Chicago, the flagship location is the world's second largest department store by square footage.

The Block 37 opened in 2009 at State and Washington, bringing with it a large group of upscale retailers to North State Street including Anthropologie, L'Occitane en Provence, Banana Republic, Zara, Disney Store, Godiva, Sephora, and an AMC Theatres location on the fourth floor.

Target opened their 125,000 square feet State Street store in the landmark Carson Pirie Scott building later in 2012.

[10] On January 12, 2012, Walgreens opened its U.S. flagship location at Randolph Street,[11][12][13][14] where it had previously existed from 1926 to 2005,[15] when construction of Joffrey Tower necessitated its demolition.

[16][17] The flagship store included retail shopping, Chicago Bulls memorabilia, a training lab for local youth, and a basketball court on the upper levels.