The shopping center features the traditional retailers Macy's and Nordstrom, in addition to a CMX luxury cinema.

The mall features prominent specialty retailers such as Vineyard Vines, Madewell, Anthropologie, Fabletics, Kendra Scott, Tory Burch, and Warby Parker.

[1][2] The huge Marshall Field & Company anchor store was the first portion of the mall to open, on October 22, 1956.

Saks Fifth Avenue moved to a larger location in 1978, selling their previous store to Lord & Taylor.

In addition to a 200,000-square-foot (19,000 m2) Nordstrom, Old Orchard also expanded the mall by 100,000 square feet (9,300 m2) as part of a $200 million expansion.

[9] The shopping center was completely redesigned in the 1990s, with the opening of the Nordstrom department store on October 7, 1994[10] and Bloomingdale's, Abercrombie & Fitch, Ann Taylor, Cache, FAO Schwarz, The Limited, Record Town, Talbots and Victoria's Secret in September 1995.

[20] The previous Lord & Taylor store is planned for reconstruction as part of a future enhanced development including additional retail, an outdoor plaza, and residences.

[23] In August 2022, it was announced that Bloomingdale's would transition to a new store format called Bloomie's in the location of the former Barnes & Noble.

[25] By 2023, Westfield Old Orchard announced several new additions, including Psycho Bunny, Tory Burch, Rodd & Gunn, Louis Vuitton, Fabletics, as well as new medical office space.

[2] It also announced that the former Lord & Taylor space would be replaced by Arhaus, Puttshack, and a relocation of the existing ZARA store.