DK Travel : Chicago

Big-city sophistication combined with small-town hospitality create the perfect blend in this, the Mid west’s largest city. Chicago’s influential architecture, cuisine for every budget and taste, great shopping, diverse ethnic neighborhoods, and outstanding museums are reason enough for a visit. And the icing on the cake? The city boasts a lakefront and park system that are as beautiful as they are recreational.

Ogilvie Transportation Center

Rising 40 stories in waves of glass and steel is this striking 1996-rebuilt commuter train station (aka the Northwestern Station). Its streamlined façade mimics a vintage luxury train.
Old Navy

This regional flagship store offers the ultimate Old Navy shopping experience, with two floors of discount jeans and T-shirts, and other casual comfort clothes at bargain prices.
Old St. Patrick’s Church

Chicago’s oldest church (1856) is crowned by two towers – one Romanesque, one Byzantine – symbolizing East and West.
Old Town Art Fair

This 50-year-old fair installs 250 artist booths along Old Town’s historic and leafy lanes. The artwork is supplemented by food vendors, kids’ entertainment, and garden tours.
Old Town School of Folk Music

Since the 1950s the Old Town School has brought world and homegrown folk music performers to Chicago. Its new home in Lincoln Square opened in 1998 with a concert by Joni Mitchell, though you’re more likely to catch a women’s ensemble from Mali and contemporary folkies such as Patty Larkin.
Olive Park

A pocket-sized park just beside Navy Pier, Olive Park makes great strolling grounds. Jutting into Lake Michigan just off Ohio Street, it provides skyline views similar to Navy Pier’s though without the tourist mobs. Quiet and out of the way, this is one of the city’s most romantic parks.
Omni Ambassador East

In its heyday, this lavish hotel hosted stars such as Frank Sinatra and Liza Minelli. Comfortable rooms sport dark wood furniture and chintz furnishings; public areas are more impressive.
One North LaSalle

This 1930-built, 49-story building was Chicago’s tallest for 35 years, and is one of the city’s best surviving examples of Art Deco architecture.
Opera

Trendsetter Opera serves contemporized Chinese food in a former 1930s warehouse. Don’t miss the five-spice squid and slow-braised pork.
Oprah Winfrey

TV’s talk-show darling (1954–) has filmed in Chicago since 1984 and become an honorary native of the city.

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