Origins in the Roaring Twenties (1926)
The Ambassador Chicago hotel (originally known as the Ambassador East) opened its doors in 1926, at the height of the Jazz Age. Visionary hoteliers Frank Bering and Ernie Byfield built the 17-story hotel on Chicago’s Gold Coast, atop the site of the old Huck Brewing Company. (In fact, workers discovered and cleared a network of old beer tunnels beneath the site during construction – a remnant of the brewery that once aged lager in underground vaults.) From the start, the Ambassador was surrounded by the stately mansions of the Gold Coast elite, an address that signaled exclusivity and style. The hotel embraced an intimate, residential charm – sometimes called Chicago’s first “boutique” hotel – offering an upscale but home-like atmosphere nestled among the city’s most affluent blocks. It quickly became the place for high society visitors to stay; as a 1960s postcard boasted, the Ambassador catered “to the world’s famous and fashionable” in the heart of the Gold Coast.
A Tale of Two Hotels (and a Secret Tunnel)
When Byfield built the Ambassador East, he already owned a successful sister property across the street, the Ambassador West Hotel. He envisioned the two as complementary twins – and even had an underground tunnel constructed beneath State Street to connect them. This secret passage was used by staff (and the occasional adventurous guest) to shuttle between the East and West without braving Chicago’s weather. In its heyday, luggage, linens, and trays of food are said to have traveled back and forth underground, enabling the two buildings to function as one grand complex. The tunnel also gained a bit of legend among local youths – neighborhood kids who snuck in recall exploring the passageways under the street as a thrilling adventure. For Byfield, the tunnel was practical and whimsical: a literal link uniting his twin hotels, which together formed an 800-room hub of luxury in the 1920s.
Shops, Services, and “Sarah Siddons Walk”
As a self-contained luxury enclave, the Ambassador East boasted more than just guest rooms. In its lower levels, an arcade of shops and amenities once catered to every need of its well-heeled clientele. Guests could pop into the hotel’s barbershop for a trim or the beauty salon for a stylish coiffure before a night on the town. A newsstand and gift shop stood ready with newspapers, magazines, souvenirs, and travel sundries. High-end boutiques even operated on-site – one fashionable dress shop was run by a local doyenne who outfitted Chicago’s socialites without them ever leaving the hotel. Byfield gave some of these areas colorful names; the hotel’s sprawling ground-floor corridor was dubbed the Sarah Siddons Walk, evoking an elegant promenade (named after an 18th-century British actress) and often lined with displays. Other in-house venues included the Buttery and the Parade – intimate lounges or dining rooms – and even a clubby bar called the Beau Nash (a nod to an old English dandy) . These shops and spaces made the Ambassador a lively gathering place for locals as well. Neighbors would drop by to browse the bookstand, sip a cocktail, or have a suit pressed, making the hotel a mini-community hub on the Gold Coast.
The Pump Room and the Golden Era (1938–1960s)
The true crown jewel of the Ambassador East emerged in 1938, when Ernie Byfield unveiled The Pump Room – a swanky restaurant and supper club inside the hotel that soon became world-famous. Byfield drew inspiration from the Pump Room of Bath, England (an 18th-century high-society haunt), and his Chicago version captured that same sense of glamour and indulgence. He transformed a formerly unremarkable dining hall with crystal chandeliers, tufted ivory leather banquettes, and a lavish entrance featuring an actual pump fountain, creating a stage fit for celebrities. The Pump Room quickly entered legend. In the 1940s, Life magazine marveled at its “café society” scene – white-jacketed waiters carrying flaming shish kebabs on swords, “coffee boys” in exotic plumed costumes pouring java with theatrical flair, and flashbulbs popping as gossip columnists photographed the stars at their tables. Byfield himself would personally meet VIP guests at the train station and whisk them to the hotel, ensuring Chicago layover travelers made The Pump Room their first stop.
The Pump Room’s Booth One became the most coveted seat in Chicago. Tucked in a corner with a perfect view of the room, Booth One was perpetually reserved for Hollywood royalty and heads of state. Even if the restaurant was packed, that semi-circular booth sat empty until a worthy celebrity arrived to claim it. Frank Sinatra, Elizabeth Taylor, Humphrey Bogart and Lauren Bacall – these luminaries and more all held court in Booth One over the years. A private telephone was installed at the table so VIP diners could discreetly field calls mid-meal (or fend off unwanted visitors by draping the long phone cord like a velvet rope). “This was the place where all the VIPs were,” remembered restaurateur Rich Melman, who would later oversee the Pump Room . Indeed, during the 1940s and ’50s, dining at the Ambassador’s Pump Room was essential for anyone seeking a taste of high society.
During this golden era, the guest register read like a who’s-who of 20th-century icons. Movie stars such as Marilyn Monroe, Robert Wagner and Natalie Wood, Marlene Dietrich, John Barrymore, Jayne Mansfield, and Clark Gable all dined or stayed at the Ambassador. Comedians Jack Benny, Jackie Gleason, Jerry Lewis, and Phyllis Diller made appearances – the latter quipped that if you didn’t get seen at the Pump Room, you might as well not have been in Chicago at all. Even famed artist Salvador Dalí paid a visit and left behind a doodle on a tablecloth as a surreal memento . Political royalty came too: the Duke and Duchess of Windsor (former King Edward VIII and Wallis Simpson) were hosted in plush style , and on a November night in 1960, Senator John F. Kennedy’s campaign team (including brother Bobby) huddled in a quiet corner of the Pump Room, allegedly finalizing Chicago’s crucial votes in that year’s presidential election. During another storied evening, an Ambassador patron grew so annoyed by fashion designer Oleg Cassini’s loud language that he challenged him to step outside and settle it man-to-man – an anecdote that only burnished the Pump Room’s reputation for nightly drama .
The hotel itself hosted long-term celebrity residents. Broadway legend Gertrude Lawrence practically lived in Booth One for a three-month run in 1940, prompting the staff to affix a plaque in her honor . Actress Helen Hayes, singer Eunice Kennedy (of the Kennedy clan), and screen siren Lana Turner all at one time made the Ambassador their home address. In 1959, Queen Elizabeth II graced the Ambassador during her royal visit to Chicago – she and Prince Philip attended a luncheon in the Guildhall ballroom, adhering to a 60-page protocol while curious crowds gathered outside for a glimpse of the monarch. That same year, director Alfred Hitchcock and actor Cary Grant filmed scenes for North by Northwest on-site at the hotel, immortalizing its elegant lobby on the silver screen. (Hitchcock took up residence in a lavish suite during the shoot, and Judy Garland happened to be staying in the penthouse at the time – so Cary Grant had to settle for a different room! ) In short, the Ambassador Hotel and its Pump Room were the center of Chicago glamour. They even found their way into song: a 1939 Hollywood musical included the lyric, “We’ll meet at the Pump Room – Ambassador East – to say the least, on shish kebab and breast of squab we will feast”, and Sinatra himself sang about “Chicago’s jumpin’ Pump Room” in his tributes to the city .
Changing Times and Legendary Tales (1970s–1990s)
As the 1960s gave way to the ’70s, the Ambassador’s golden age began to wane. Ernie Byfield passed away in 1950, and without its colorful founder at the helm, the hotel and Pump Room faced gradual decline . By the mid-1970s the Pump Room had lost some of its luster – it even filed for bankruptcy in 1975 . Salvation came in the form of Chicago’s burgeoning restaurant empire, Lettuce Entertain You Enterprises, which bought the Pump Room and spruced it up, determined to restore its elegance (the new owners, however, did quietly retire some of the more outdated quirks, like the waiters’ white turbans and those tableside telephones) . The dining room got a facelift, but its star power continued. A new generation of celebrities embraced the tradition: during the 1973 filming of The Sting, Paul Newman and Robert Redford lunched on ham sandwiches and beer at Booth One every day. Comedian Mel Brooks became a regular, greeting fellow guests with jokes, and young stars like Eddie Murphy and Michael J. Fox stopped in during the 1980s.
Upstairs, the hotel itself was changing hands and identities. In 1978, the Ambassador East was sold to Dunfey Hotels, ending its era as an independent grande dame. The new owners rebranded it as Ambassador East – A Dunfey Classic Hotel, and a few years later it became part of the Omni Hotels chain (Dunfey’s parent company). Despite the corporate management, the Ambassador’s mystique endured. Omni poured $20 million into a major renovation in 1999, carefully updating guest rooms and infrastructure while striving to retain the hotel’s historic charm. Glimmers of the old glamour remained: the hotel was still pet-friendly in over-the-top ways (dating back to Byfield’s policy of pampering guests’ dogs with special meals and monogrammed bedding ), and visiting stars continued to drop by. In the 1980s, Phil Collins famously ran afoul of the Pump Room’s dress code – arriving without a jacket, he was denied entry by the doorman. The British rocker later humorously titled his 1985 album “No Jacket Required” in tribute to that snub, and the Pump Room sent Collins a custom sport coat as a peace offering . (By that time, the restaurant had finally relaxed into a more casual dress standard, but the legend of the jacket lived on.) Even Sonny Bono got a small footnote in history as the first man ever allowed to dine at the Pump Room without a tie or jacket – perks of celebrity, which poor Collins didn’t enjoy since staff hadn’t recognized him at the door.
Through the late 1990s, the Ambassador East remained a beloved if slightly faded icon. Chicagoans of a certain age remember dressing up for dinner at the Pump Room or cocktails at the tiny Beau Nash lounge. Society events, from charity balls to weekly “tearoom fashion shows” hosted by local boutiques, continued to animate the hotel’s public spaces well into the ’80s. The Ambassador had become a living museum of its own past – one could stroll the halls and see walls lined with framed autographed photos of the luminaries who stayed or dined there over the decades. This living history made it a favorite for nostalgic travelers. Still, by the early 2000s, it was clear the old hotel needed a new vision to thrive in a changing hospitality market.
Reinvention in the 21st Century
In 2005, the Omni Ambassador East was sold to a local development group, which considered converting the aging building into high-end condominiums . Chicagoans feared the storied hotel might permanently close, but the condo plan fizzled, and the Ambassador continued as a hotel. A major turning point came in 2010 when boutique hotel impresario Ian Schrager (of Studio 54 fame) purchased the property . Schrager, known for reinventing classic hotels with modern chic (like New York’s Gramercy Park Hotel), saw potential in the Ambassador’s bones. He closed the hotel for a top-to-bottom makeover and in 2011 reopened it under a new name: PUBLIC Chicago, attempting to fuse the building’s Jazz Age glamour with minimalist contemporary design. The Pump Room was reimagined with a sleek update by celebrity chef Jean-Georges Vongerichten, and for a few years the hotel drew a trendy new clientele. Gone were the walls of celebrity photos and some of the old-school formality; in their place came clean lines, neutral tones, and a hip vibe. Yet even as it changed, the hotel never hid its lineage – Schrager referred to PUBLIC Chicago as a “historic reboot,” keeping the Pump Room name alive and preserving Booth One for nostalgia’s sake.
The whirlwind of ownership changes continued, reflecting the hot real estate market for vintage hotels. In 2017, the Ambassador property was sold again, and this time the new owners restored its original name, dubbing it Ambassador Chicago once more . They knew the power of nearly a century of goodwill. The Pump Room, however, faced a bittersweet end: it served its last meal in 2017 as the hotel transitioned management. (For a couple of years, Lettuce Entertain You Enterprises – the same group that saved it in 1975 – ran a revamped restaurant in the space called “Booth One,” but that too closed in 2019 .) In 2020, Ambassador Chicago joined Hyatt’s boutique collection (the Joie de Vivre brand) with plans for further refurbishment…only to be tested by the COVID-19 pandemic that struck shortly after. The hotel, like many, had to pause operations for nearly a year during the height of 2020’s lockdowns. It was a challenging chapter, but by 2021 the Ambassador had reopened, resilient and refreshed.
Legacy and Present Day
Today, the Ambassador Chicago embraces its legacy as an icon of hospitality – a rare 99-year-old survivor from Chicago’s Jazz Age that still welcomes guests in style. The hotel has been lovingly updated for modern comfort while retaining the spirit of 1920s elegance. Visitors stepping into the lobby will notice vintage black-and-white photographs of famous guests adorning the walls, and the hotel’s 285 rooms include suites named after the luminaries who once slept there. Downstairs, the old Pump Room space has been reborn as The Ambassador Room, an in-house restaurant that nods to its predecessor by offering classy supper-club vibes and “old-school English” touches in the adjacent Library bar lounge. Though Booth One is no longer the paparazzi magnet it once was, you can still request to sit there and imagine Frank Sinatra or Elizabeth Taylor by your side.
The Ambassador’s location remains as prestigious as ever – nestled on a quiet, mansion-lined street, yet just steps from the Magnificent Mile’s shopping and the lakefront’s beauty. As Chicago’s “original boutique hotel” dating back to 1926, it now balances historic charm (ornate moldings, a grand staircase, and that cozy, wood-paneled Library bar) with contemporary luxury (plush bedding, a 24-hour fitness center, and modern tech amenities). The hotel continues to host celebrities and travelers seeking an authentic Chicago experience – one that comes with nearly a century of stories.
In its 99 years, the Ambassador has seen it all: Prohibition-era parties, wartime banquets, movie stars and royalty, jazz trios and rock bands, makeovers and near-closure, and triumphant rebirths. It stands today not just as a place to stay, but as a living museum of Chicago’s cultural history. For visitors and locals alike, walking into the Ambassador Chicago is like stepping back in time – you can almost hear the echo of clinking cocktail glasses and Big Band music drifting from the ballroom. Yet it’s also very much alive in the present, still offering the warm welcome and glamour that made it famous. As you explore its halls, you’re walking in the footsteps of legends – and adding your own chapter to the ongoing story of the Ambassador Hotel Chicago.
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