For some, the height of luxury is all about modernity and having access to the newest, hottest and trendiest things around. But for many others, there is nothing more glamorous than classic luxury that stands the test of time. If you fall into this second group, then you probably prefer to ride around in a 1950s Rolls Royce wearing vintage couture and bellying up to the bar in the kinds of hotels Sinatra used to stay in. And in Chicago, no one would blame you. This is an old city that treasures its history and is fiercely proud of the things that have made it what it is today. Here is a guide to exploring Chicago through the help of a proverbial time machine.
Built in 1920, The Drake hotel is a beaux-art property whose very name is synonymous with grandeur and class. Imagined as an “urban resort,” The Drake was the place to see and be seen…and oh, whom you could see! The illustrious list of former guests and visitors include Charles Lindbergh, Walt Disney, Bing Crosby and George Gershwin. It was also on the wooden bar of the hotel’s Cape Cod restaurant that blushing newlyweds Marilyn Monroe and Joe DiMaggio carved their initials.
For those who prefer a modern homage to the past, Thompson Chicago hotel is the place to stay. The opulent yet sleek, mid-century design aesthetic is so spot-on you may even be looking for Don Draper to swagger around the next corner. And the setting could not be better. Located right in the heart of the glitzy Gold Coast neighborhood, the hotel’s rooms look out onto a glittering skyline and expansive Lake Michigan.
When it comes to dining, Gene & Georgetti’s may not look like much from outside, but this upscale establishment has been a Chicago institution since 1941. Housed in a building that was completed just a year after the Great Chicago Fire in 1872, it’s long been a favorite among the rich and fabulous. The décor looks like it probably hasn’t changed much since Sinatra used to hang out here (in a good way), and the service is that special brand of old-school excellence you don’t find in many restaurants anymore.
If you’re looking for the epitome of a Chicago steakhouse with a vibe that is equal parts classic and chic, Gibson’s is it. All dark wood, leather banquettes and low lighting, Gibson’s embraces the traditional elements of a fine steakhouse but with a speakeasy feel. This has and will always be a favorite amongst movers and shakers. The quality and menu are consistent and that’s just the way they like it; Gibson’s is not a place that would be caught trying to be trendy, flashy or anything other than the refined staple they’re known to be.
For an old-school, super luxe shopping experience, head a bit off of the famed Magnificent Mile to a small stretch of Oak Street that is lined with designer boutiques housed in beautiful old brick townhouses. This is no mall or chaotic shopping district, but a serene and picturesque place where patrons are treated the good old-fashioned way, with personalized service from attentive sales associates and stylists. Duck into Barneys, Hermès or Jimmy Choo for a few fabulous new outfits to wear for your nights out on the town.
It’s a good 20-minute cab ride from downtown Chicago, but this venerable jazz bar used to be Al Capone’s unofficial clubhouse, so it’s well worth the fare. Although the clouds of smoke and zoot suit gangsters might be gone now, The Green Mill’s cocktail lounge’s deep, round booths, art deco décor and live music lineup will certainly send you back in time. You might spot college students in jeans here, but you’ll also be perfectly at home dressed up and sipping a fancy drink, which is part of the beauty of The Green Mill.
The Pump Room has had a somewhat modern makeover, but this revered locale has been a VIP hotspot for decades. Everyone from Paul Newman to Audrey Hepburn and Dean Martin have graced the place and it is referenced in the two most iconic songs about Chicago. The updated restaurant pays homage to its rich history with a supper club-type atmosphere and, of course, a wall of photos that reminds you that you’re in the hallowed halls where the likes of Bogie and Bacall once drank and made merry.
There’s no shortage of luxury in Chicago, but the spots that bring to mind an extravagant life of yore are slightly harder to find. But if you look hard enough, you’re sure to get a whiff of the old school luxuriousness that The Windy City once exuded.
