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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.

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