Chicago, Illinois – the hometown of US President Barack Obama — is booming. In 2011 the Windy City welcomed 44 million visitors, an 11% increase on the year before; last June, hotels hit a record 92% occupancy rate; and Chicago O’Hare International Airport, already one of the world’s busiest, is getting busier, with Cathay Pacific’s recent addition of nonstop flights to Hong Kong, and Qatar Airways adding nonstop flights to Doha next April.

To keep up with demand, a number of high profile hotels are under construction. In 2013, the Hong Kong-based Langham Group will open a 316-room luxury hotel in the former IBM building, originally designed by Mies van der Rohe; Richard Branson’s newest venture, Virgin Hotels, plans to open its first property in a renovated Dearborn Bank building downtown, and the 800-room Hyatt Regency McCormick Place will open a new 461-room tower.

Why all the activity? Because Chicago has a talented workforce and a central US location with extensive airline service, which makes it ideal for corporate headquarters such as Boeing, Hyatt, Motorola and United Airlines.

Located on the western shore of Lake Michigan, Chicago is bisected by the Chicago River. The downtown commercial core of the city just south of the River is known as “The Loop” with upscale districts such as River North and the Gold Coast to the north and the enormous McCormick Place convention centre to the south.

Most international flights arrive at the sprawling Chicago-O’Hare airport, located 17 miles west of downtown. The city’s secondary airport, Chicago-Midway, 10 miles south of the city, is primarily used by low-fare domestic carriers such as Southwest Airlines. Both are connected via rail to the city’s metro system, known locally as “the L”.



Hilton’s iconic Waldorf Astoria brand scored big when it took over the Elysian — one of Chicago’s newest and most talked about five-star hotels — and renamed it the Waldorf Astoria Chicago in February 2012. This elegant 60-storey limestone tower also houses 52 private residences, a restaurant and bar (Balsan and Bernard’s Bar) and is frequently cited by reviewers as one of the best hotels in the US for its stellar service, and elegant touches like Carrera marble bathrooms and fireplaces in nearly every room.

The 339 modern rooms at the imposing, steel-and-glass Trump Hotel Chicago soar above the Loop, many with giant all-limestone bathrooms, fireplaces, kitchens and floor-to-ceiling windows with expansive city and water views. The hotel’s contemporary Sixteen restaurant, located on the 16th floor, has quickly earned a reputation as one of the best in town, offering classy continental cuisine as well as creative local fare (like fried smelt, a fish, from Lake Michigan).

At the five-star Peninsula Chicago, Midwestern hospitality meets Asian-style service. For example, guests can request a ride in one of the hotel’s classy “Peninsula green” Mini Cooper S Clubman cars – a smaller, cuter take on the well-known fleet of dark green Roll-Royces on offer at the Peninsula’s flagship hotel in Hong Kong. And with corporate headquarters nearby, you can always count on a stay at the198-room Park Hyatt Chicago to exceed expectations.


Pop-hotelier Ian Schrager has taken his reputation for over-the-top luxury down a notch with PUBLIC Chicago, which opened in 2011 in the old Ambassador East Hotel building. With a stronger focus on service than style, all 285 rooms are modestly priced and minimalist chic with what the hotel calls “a soothing no colour palette”. Room service meals are delivered without delivery charge, and wi-fi is free. For a little local history, check out the re-imagined Pump Room, the original hotel’s famous bar/restaurant once patronised by stars such as Frank Sinatra, Bette Davis and Mick Jagger, which now features fresh farm-to-table fare from celeb chef Jean-Georges Vongerichten.

In late 2011, design-forward Radisson Blu, with several popular hotels in Europe, opened its first US property, the 334-room Radisson Blu Aqua Hotel on the first 18 floors of the famously wavy 86-story Aqua Building, designed by acclaimed architect Jean Gang. Business travellers tired of cavernous, windowless rooms will rejoice at the hotel’s meeting space – most of which is bathed in full daylight, with floor-to-ceiling windows looking out on city skyline, Millennium Park and Lake Michigan.

The comfortably chic, 63-room Ivy Hotel is small by Chicago standards: there are only five rooms per floor in this recently remodelled mid-century office building – all with modern platform beds swathed in Egyptian cotton sheets, bathrooms with large soaking tubs and eco-friendly touches like bamboo flooring. Added bonuses include a popular rooftop bar and free wi-fi.

If you feel like getting out of the (expensive) Loop and experiencing Chicago like a local – or if your meetings are on the north side of town — check into the retro-chic Hotel Lincoln. This newly renovated, 12-storey, 184-room property is located in the heart of Lincoln Park, one of the city’s trendiest neighbourhoods.

Expense account
Chicago has plenty of world class restaurants that are perfect for a celebratory meal with clients or colleagues. But with the world coming to Chicago, finding an available table at one of the city’s top restaurants is difficult – so book well ahead of time, employ your hotel concierge or tip the maitre d’ generously, especially when citywide conventions or tradeshows are in town.

For modern preparations of classic game dishes (like smoked squab or roasted duck) and a wine list revered by Food & Wine magazine, book a table at Henri on Michigan Avenue across from Millennium Park. On the western edge of downtown, the understated, uber-popular Urban Union offers fare such as wood-oven roasted marrow bones, whole fish or lobster in a rustic atmosphere – think brick, rough hewn wood and steel chairs – making it a great spot for a laid back, classy meal.

RPM Italian is the place for house-made pasta dishes such as king crab spaghetti or duck agnolotti with figs and Brussels sprouts – served by white-jacketed waiters in black and white surroundings. For years, Topolobampo has been serving up authentic, high-end Mexican cuisine and a menu of constantly changing dishes like ceviche (marinated raw fish), chile relleno filled with pork belly, fruits and nuts) or barbacoa de borrego (wood-oven roasted lamb, wrapped in maguey leaves).

For classic American cuisine in an elegant space, visit Sepia, originally a 19th-century printing shop, and order the apple cider consommé with pork and chestnut dumplings or a prime strip steak with maitake mushrooms. At the three-Michelin-starred Alinea and its spawn, Next, chefs turn out visually arresting, taste-bud-exploding dishes (such as a lemongrass, cucumber and basil refresher served from a small glass tube) that seem to come from a laboratory instead of a kitchen.

Go local
When you are in an all-American city like Chicago, it is only appropriate to grab a hot dog at one of the many Portillo’s hot dog stands or at a sporting event like a Chicago Cubs baseball game at Wrigley Field. To make it truly local, pile on condiments such as diced onions, relish, mustard, celery salt, peppers and pickles. But do not slather it in ketchup, which “Chicago-style” aficionados say is unacceptable.

Off the clock
Instead of just gazing up and wondering about Chicago’s distinctive and powerful architecture, learn all about it on a Chicago Architecture Foundation River Cruise. From May through November, the expert-led, 90-minute cruises highlight 53 historic and architecturally significant sites, including Trump Tower, Merchandise Mart, Wrigley Building, Tribune Tower, and the Willis (formerly Sears) Tower.

Don’t do this!
Traffic between the city and its airports can be treacherous and unpredictable, so do not wait until the last minute to leave. If you only have a few bags, taking the L between the city and O’Hare takes a predictable 45 minutes; the trip to Midway is 25 minutes. But if you have large bags, if your hotel is not located near a rail station or if you just prefer to take a cab, car or bus, the length of the trip to either airport can be as short as 25 minutes or as long as 90 minutes, depending on traffic.