It’s been called “Chi-town, “Windy City”, “Second City”, “City of Big Shoulders” and most notably “the most American of big cities”. If you haven’t guessed what place we’re talking about yet, here’s a few more clues. This city has also launched the careers of powerful politicians such as current US President Barack Obama and been home to gangsters like Al Capone and John Dillinger, athletes such as Michael Jordan, notable musican Nat King Cole, actors Harrison Ford and John Malkovich, soap star Oprah Winfrey, and writers like Michael Crichton, Philip K. Dick and Ernest Hemingway.
Yes it’s Chicago and it certainly has big shoulders as this list of famous people attests. It’s also the third most populous city in the United States, home to 2.8 million residents and is one of the world’s top 10 Global Financial Centres.
Chicago blends something of the sophistication and elegance of America’s big cities with the warmth and friendliness of its mid-Western people. In Chicago you can enjoy sights, sounds and pleasures as diverse as adding designer labels or jewelry to your suitcase in any of the 460 storefronts along the Magnificent Mile, an incredible choice of nightlife including the city’s famous blues music or theaters, plenty of gob-smacking food such as the Chicago pizza, an array of architecture, skyscrapers and art to take in, or the beautiful lakeside location by Lake Michigan.
This is a town that is packed full of things to see and do, with enough attractions, tours, events and festivals to satisfy the most curious mind. Millennium Park and Navy Pier are good places to start, while a trip to the 104th-floor Chicago Skydeck offers breathtaking 360 degree views taking in the amazing cityscape and four states. There’s loads to do and Chicago is easy to get around, while if you’d prefer to let someone else do the work for you there are plenty tour operators offering every kind of daily excursion imaginable.
While the city’s lakeside setting does mean it gets a little windy at times, don’t be too worried about inadvertent weather. The term “Windy City” was actually coined in the 1800s by reporters about the boastful local politicians. However, do note the best time to visit is usually from April through October. The lakeside features miles of parks and is really one of the city’s best features and something of a playground for Chicagoans. It’s a great place for a stroll, biking, jogging or sailing or simply to get photographs of downtown.
Another great way to get views of the city is to ride the Brown Line elevated train, known as “the El”. The lines crosses the Chicago River and wanders through the downtown sky scrapers and is a real experience of the city.
Some of Chicago’s famous hotels are almost tourist attractions in themselves too and read like a list of credits – The Allerton, The Drake Hotel, The Elysian, The James Chicago and The Whitehall Hotel. No doubt you’ve heard of some of them and if you’re bedding down in this most American of cities and taking in some of the essence of its gastronomy, mighty politics or monuments of Michigan Avenue, do consider one of these five places for a truly Chicago experience.
Rising 25 stories above Chicago’s Magnificent Mile, the Allerton Hotel has been a Windy City favorite for close to a century. Since it first opened its doors in 1924 it has built a reputation for luxurious yet affordable accommodation in the heart of Chicago. Much of the Allerton’s charm lies in its unique combination of the old in the new. Designated as a historic landmark it exudes old-word charm, while a multi-million dollar renovation in the late ‘90s transformed it into one of the most modern and luxurious boutique hotels in the city. The Allerton has a rich history and was famously the home of the swanky penthouse ‘Tip Top Tap’ lounge through the ‘40s and ‘50s. The same room was used as the studio for the popular ‘Don McNeill’s Breakfast Club’ in the ‘60s. Today, the guests who walk Allerton’s hallways follow in the footsteps of the Hollywood stars and international dignitaries who have stayed there down the years, and enjoy a level of comfort and service to match.
Since the Drake Hotel opened its doors in 1920 it has remained one of the most luxurious places to stay in Chicago. Today it combines its historic character with all of the comfort and facilities one would expect from a modern five-star hotel. The consistent quality of the Drake is reflected in the famous faces that have passed through its lobby down the years. Overseas aristocracy and dignitaries include Winston Churchill, Princess Diana and Prince Charles. Of course there was also a generous smattering of celluloid celebs. Marilyn Monroe, Frank Sinatra and Judy Garland, to name a few. The guestbook reads like an autograph collector’s dream, but with 525 luxurious rooms that aren’t outrageously priced, a stay at the Drake isn’t only reserved for the beautiful people.
THE ELYSIAN
The Elysian Hotel seeks to envoke the “lost art of travel” when hospitality was luxurious, an overnight stay a real escape from reality and staff attention was common courtesy. One of the ways they have tried to recreate the indulgent aspect of travel is by providing plenty of space – there are 188 rooms but just 10 per floor with an average of 890 square feet. In each the closets are expansive and bathrooms feature white Carrera marble bathrooms with soaking tubs, separate showers and dual vanities with inset LCD televisions. Fireplaces, outdoor terraces and family rooms with master bedrooms also reinforce this feeling of roominess. Guests also enjoy all the advanced in-room technology you would expect with such luxury such as LCD high-definition televisions, touch screen VoIP telephones and wireless internet. The Elysian also has classy dining establishments and 24-hour room service and guests receive complimentary access to the Elysian Spa & Health Club.
THE JAMES CHICAGO
Located right in downtown Chicago, The James Chicago is located near Michigan Avenue and some of the best dining, shopping and nightlife action Chicago has to offer. This boutique luxury hotel has everything from standard guest rooms to luxurious Loft Penthouses and all have been designed to give guests the comforts of home combined with all the touches you would expect from a stellar hotel. In fact everything about The James speaks of embodying a contemporary lifestyle with a relaxed and comfortable flavor. This guest-centric ethos means there are little inhouse perks such as valet parking, dimmable lights, custom James robes and slippers to use, private dining niches and even a welcome extended to your pets. Other facilities at The James Chicago include the signature restaurant, Primehouse, with celebrated chef David Burke. There’s also the neighbouring J-bar, gym and spa facilities and conference rooms and function spaces for business guests and social events.
THE WHITEHALL HOTEL
Fortune Magazine called The Whitehall Hotel “one of the eight great small hotels of the U.S.” And with a recent renovation it has indeed been returned to its original 1920s grace, grandeur and splendour with a distinctive European feel. Intimate and luxurious, look no further than The Whitehall’s tufted leather chairs, elegant wooden panelling, marble bathrooms, stylish parlors and chandeliers for real old world charm. However there are modern conveniences too – business and event facilities, 24-hour room service, high-speed internet, a fitness center and concierge. This boutique hotel also offers you a feast for your culinary senses too with a pan-Italian restaurant and classy lounge bar where you’ll be keeping good company – the Beatles once enjoyed a drink here as well.
