As an airfield, the land served as the take-off site of many famous aviators such as Amelia Earhart and Wiley Post. Charles Lindbergh's solo transatlantic flight took off from Roosevelt Field in 1927. The field was originally named Hazelhurst Field and was renamed in honor of Theodore Roosevelt's son Quentin, who died in World War I. After the airfield was closed in 1951, the site was developed by New York's William Zeckendorf and designed by I. M. Pei. Ground was broken on the $35 million project in April 1955. The center opened with a single level and was an open-air center. It included F.W. Woolworth 5 & 10 store, Walgreen Drug, Food Fair supermarket, Buster Brown Shoes, a public auditorium, movie theater, and an outdoor ice rink. The original anchor of the mall was a 2-level 343,000 ft² Macy's which opened on August 22, 1956. In 1962, a 250,000 ft² Gimbels store opened. With the addition, the complex held over 1,000,000 ft². A major extension was completed in 1964. Macy's had an 85,000 ft² third level added. In 1968, The Century Roosevelt Cinema began operation. At that time, the mall was enclosed. In 1972, a second major expansion was completed which added a 3-level, 260,000 ft² J.C. Penney, which was later completely renovated in 2010, and a 2-level 31,400 ft² Alexander's. Le Petit Mall, a Tudor-style expansion was built in 1974 that architecturally reinforced the novelty of shopping indoors. An upper level of stores and food court was established in 1993 after a major renovation which started in 1991. When Alexander's went bankrupt in 1992, Abraham & Straus gutted the building and extensively renovated it, opening in 1992. The Abraham & Straus location at Roosevelt Field only lasted until 1995, when the chain became defunct. The store was slightly renovated, and re-opened as a Bloomingdale's in 1995. The Bloomingdale's store at Roosevelt Field had a major renovation, which was finished by the summer of 2009. The Gimbels anchor was a Stern's between 1987 and 2001. After Stern's closed, the spot was taken over by Galyan's, which opened in 2003. Dick's Sporting Goods occupied the eastern section and Bloomingdale's Furniture Gallery, which opened in 2004, occupied the western half until closing in 2019. A new, 3-story Nordstrom and a 2-story wing leading to the new Nordstrom opened in August 1997. Simon Property Group took ownership of the mall when it acquired Corporate Property Investors in 1998. In March 2012, it was announced that a new 100,000-square-foot building anchored by luxury department store Neiman Marcus would be added to Roosevelt Field. Opened on February 19, 2016, this expansion created room for even more shops leading up to the luxury department store and was accompanied by a new parking structure. During the renovation of the mall in 2015, the glass elevators in the center were removed to create a play area and new elevators were built to replace them. Simon had discovered that the scenic elevators had to be removed due to severe hydraulic oil leakage. According to Newsday, on June 26, 2020 Microsoft announced they were closing their store with the rest of the Microsoft stores.
