It is a cold night in Chicago and the bars in the River North neighbourhood are bleeding dance music on to the street. The city skyline glitters as if gold dust has been thrown into the night, a blaze of shiny neon. I'm standing outside an unmarked door that I'm told will lead me back in time. This is Untitled, a subterranean speakeasy where the waiters dress in crisp white shirts, braces and fedoras and the entertainment is provided by elderly bow-tied crooners in black tuxedos who gamely encourage the diners to party like it's 1929.
A saxophone moans and a barman prepares cocktails. In the whisky room, the bottles are lined up high behind the bar, glowing gold in the dim light; a huge mirror hangs on the wall. Not everything, however, is quite as it seems. The mirror is actually composed of nine plasma television screens and while Untitled may look as if it's been around since the days of Capone, it opened less than six months ago. The planners studied old photographs of 1920s supper clubs for inspiration when designing the building and the menu includes Prohibition-inspired dishes, such as grit cakes with tomato jam and bison burgers.
I had come to this cavernous venue, on the site of a former furniture warehouse because Untitled is part of a trend that has seen new bars and restaurants taking inspiration from the rich history of Chicago to create something new. Some have looked to the 1920s – the era of speakeasies and supper clubs – others, like the revived Pump Room which re-opened last year, evoke the celebrity encrusted glamour of 1950s and 60s Chicago when the likes of Frank Sinatra and Judy Garland sang in (and about) the city. "We'll meet at the Pump Room, Ambassador East, to say the least," trilled Garland.
The Pump Room is a pleasant walk from downtown Chicago to the Gold Coast district and used to be the hottest celebrity haunt in the country. When he was in town, Sinatra would call ahead to the Pump Room and offer to pay the bill of anyone seated in his private booth if they would vacate it for him and his friends. Sinatra's booth is at the back of the restaurant, and when I visited it was the only unoccupied booth – as if the waiters still half expected the call to let them know he was on his way.
The new Pump Room tries not to intimidate guests with its history, but it's hard not to – the lobby walls are lined with old photographs of stars dining there, such as Bogie and Bacall, Marilyn Monroe and Clark Gable, Chaplin and Astaire. The refitted restaurant, which opened last year as part of Ian Schrager's Public Chicago Hotel – the Studio 54 co-founder last year renamed the Ambassador East and relaunched it as a no-frills hotel – has exchanged old-school glamour for classy understatement: yellow globes like atomic structures from the periodic table hang from the ceiling and the waiters look smart but casual.
The new Pump Room is a revival of the old one, but elsewhere in Chicago old locations are being used in new ways. The Bedford, a new restaurant in the hip Wicker Park district, is located on the site of a former 1920s bank. I walked down the steps into the dimly lit wood-panelled dining room and was shown to a table next to the original bank vault. Many of the bank's original features still stand – the glass from teller windows has been made into lampshades and the bathroom stalls are the old private viewing rooms where rich folk would come to inspect their money. The undoubted highlight of the Bedford is, however, the vault with its giant circular silver door which leads into a refitted lounge. The room is lined from floor to ceiling with more than 6,000 original copper lock boxes. Candles flickered on low tables and a jewelled chandelier sparkled from the ceiling.
Later that evening I found myself searching again for an unmarked door, a pale yellow bulb dimly glowing above it. I pushed open the door and found myself in a narrow corridor which led to a set of velvet curtains. I parted the curtains and stepped into the Violet Hour. The cocktail bar, also in the Wicker Park district of Chicago, is named after a line from TS Eliot's The Waste Land. Among the house rules for entering the Violet Hour is one that warns patrons "don't invite anyone you wouldn't want to invite to visit your mom on a Sunday afternoon". The bar was a high-ceilinged candlelit room that was tastefully furnished with tall-backed chairs arranged in clusters. The cocktails and drinks on the menu are inspired by the 1920s and the bar only allows seated guests so once the seats are taken a queue forms outside.
I took a sip of a non-alcoholic cocktail made with ginger, raspberry, lemon and orange and wondered about the wisdom of a non-drinker loving a cocktail bar. The Violet Hour worked because it was not aiming for the studied fake authenticity of Untitled and it was not a revival of a historic institution like the Pump Room. It was both derivative and original: living in the present but loving the past.
Essentials
United Airlines (0845 844 4777; united.com) flies daily from London Heathrow to Chicago from £554 including taxes. Palmer House (hilton.com) has rooms from $139 (including tax). Public Chicago Hotel (publichotels.com) has doubles from $135. For more information, go to choose chicago.com