The corner of North Carolina and Pacific Avenues was farmland in 1868, when Elisha and Elizabeth Roberts paid John DaCosta $6,500 for a plot of it. They built a three-story wooden boarding house called Chalfonte House for $21,000 over the following winter and named it for Chalfont St Giles, the Buckinghamshire village where William Penn is buried. The Hunt family opened the Haddon House across the street the next year, naming theirs for Haddonfield, New Jersey, the Quaker settlement founded by Elizabeth Haddon in 1701. Both houses passed through several owners. The eight-story brick Chalfonte Hotel that replaced the wooden Chalfonte House on July 2, 1904, was Atlantic City's first skyscraper, designed by Philadelphia architect Addison Hutton. The Haddon Hall complex that became the modern hotel went up in stages through the 1920s, eventually reaching 15 stories and 1,000 rooms. By the end of the decade, Chalfonte and Haddon Hall were joined by a skyway across Pacific Avenue. The skyway still exists. You can walk across it.

During World War II, the United States Army took over forty-seven Atlantic City resort hotels and turned the boardwalk into a basic training facility called Camp Boardwalk - one of the strangest mass conversions of civilian property in American military history. The Chalfonte-Haddon Hall complex was merged with the adjacent Traymore Hotel to form England General Hospital, named for Lieutenant Colonel Thomas Marcus England, a military doctor who had worked alongside Walter Reed researching yellow fever in Cuba in 1900. The hospital opened on April 28, 1944. Soldiers convalesced in rooms where summer guests had once watched the ocean. The last patients left in June 1946, and the hotel reopened to civilians that August. Three decades later, the building would be reinvented yet again.

New Jersey voters approved casino gambling in November 1976 - a referendum to which Resorts International had heavily contributed. The company had already taken the precaution of buying control of Leeds & Lippincott, the firm that owned Chalfonte-Haddon Hall, the previous summer for $2.489 million. They closed the older Chalfonte building because its rooms could not be expanded to meet New Jersey's casino requirements, retained the Haddon Hall, and got an 18-month head start on every competitor. The building was renamed briefly to The Palace Hotel in May 1977, then to Resorts International Hotel that July, then finally opened as a casino on May 26, 1978. The first show featured Steve Lawrence and Eydie Gorme. The Super Star Theater would go on to host Frank Sinatra, Dolly Parton, Cher, Stevie Wonder, Aretha Franklin, Barry Manilow, and the Beach Boys. The space had originally opened in 1931 as a movie house.

By 1987 Resorts International had stopped reinvesting in the boardwalk property. Donald Trump bought a controlling stake in the parent company and made a tender offer for the rest. Television producer Merv Griffin counter-bid. After two months of public battle, the two men split the company between them in November 1988. Trump took the unfinished Taj Mahal tower a few blocks away. Griffin took the Atlantic City casino plus Resorts Paradise Island in the Bahamas. He also took the Sikorsky S-61 helicopters that Resorts International Airlines had been using to shuttle high rollers - or rather, he let Trump have them. Trump repainted the three green-and-orange helicopters black and red, slapped Trump Air decals on them, and used them as the founding fleet of the airline that would become Trump Shuttle. He told reporters they were the same model the President of the United States used. Griffin, meanwhile, sank $90 million into improving Resorts. Later he sold Paradise Island to Sun International for $350 million. The two men, who had been at each other's throats in 1988, had each gotten what they actually wanted.

Resorts changed hands twice more in the 2000s, lost $140 million in resale value along the way, and surrendered to its lenders in December 2009. In late 2010, former Tropicana executive Dennis Gomes took over for $35 million. His big idea was to lean into the building's actual era. Resorts already had genuine 1920s architecture under decades of carpet and wallpaper; Gomes brought back the Art Deco bones, dressed dealers in flapper-era uniforms, piped in jazz, and called the theme Roaring Twenties. HBO's Boardwalk Empire had premiered that September, and Gomes timed his rebrand to ride the show's success. In May 2011, Resorts became the first Atlantic City casino to actively market to LGBT customers, opening the city's first gay casino nightclub - a club called Prohibition. The casino has since added sportsbooks, partnered briefly with Mohegan Gaming, and gone back to operating independently as of January 2025. The skyway over Pacific Avenue still connects Haddon Hall to what is left of the old Chalfonte property next door. The dice still roll on tables four floors below it.