The mall has been a hub for commercial activity and development, driving dramatic growth in the surrounding area for the past 20 years.

Orland Square opened on March 15, 1976 with JCPenney, Marshall Field's, Sears and Carson Pirie Scott.

[7] In 2006, Macy's took control of the Marshall Field's location upon being purchased from Federated Department Stores and May Company.

[10] Orland Square went under another renovation in 2012 that completely changed the image of the mall, with upgraded entrances, signs, floors, as well as lighting and expanded food court.

On November 4, 2016, an entertainment center called Gizmo's Fun Factory opened along with Sky Zone Trampoline Park to the left of the nearby Carson's Furniture Gallery.

[14] In January 2018, it was announced Sears would shutter as part of an ongoing decision to eliminate its brick-and-mortar format.