Last Updated: 10/06/09
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Walking around the historical center of Chicago, or what locals call "the Loop," you'll find your gaze drawn inexorably upward. All around you are some of the most striking and diverse architectural styles in America. Just as your eye catches an elaborate Art Deco detail in one direction, you'll spot an ultra-modern tower in the other. Old mingles with new in what amounts to a living museum of buildings from the second half of the 1800's to the present.
Chicago doesn't have mountains like Denver or beaches like Miami. It has buildings. Sure, as the nation's third largest city, Chicago serves up world-class attractions like museums, an active arts scene and championship sports teams -- as well as homegrown favorites like deep-dish pizza, Oprah and the Blues Brothers. But it's in architecture that the Windy City really shines.
This is in fact the birthplace of the modern building. The world's first skyscraper, the Home Insurance Building, was built here in 1885, and while that building was taken down in the 1930's, Chicago is today home to three of the tallest buildings in the world: the Willis Tower (formerly known as the Sears Tower, it stands at 1,450 feet), AON Center (1,136 feet) and John Hancock building (1,127 feet). Head up to the Willis or Hancock observation decks and you'll look down over a city shaped by architectural innovators like Daniel Burnham, Louis Sullivan, Mies van der Rohe and Frank Lloyd Wright.
Chicago did not start off on such a grand scale. The city was founded at the mouth of the Chicago River in 1779 by Jean Baptiste Point du Sable, a fur trader from Santo Domingo. But by 1848, with the completion of the 100-mile Illinois and Michigan Canal connecting the Chicago to the Mississippi, this little trading post was on its way to becoming a major transportation hub. The "Great Chicago Fire" in 1871 dealt a devastating blow, but the city rebuilt with the help of pioneering architects like Burnham, whose motto "Make no little plans" was well embraced.
Chicago is at its most impressive along the "Magnificent Mile" portion of North Michigan Avenue, where visitors will delight not only in the upscale shops but also such striking attractions as the Gothic Tribune Tower, home of the Chicago Tribune newspaper, and the Beaux-Arts Wrigley Building. To see how the design innovation continues, check out the work of renowned contemporary architect Frank Gehry at Millennium Park, opened in 2004. The park has become so much a part of the Chicago scene it's been dubbed "the people's park."
Downtown Chicago has the largest business district in the U.S. outside of Manhattan, and it's all hustle and bustle. The streets literally fill with people at lunch hour when all the office towers seem to spew forth their occupants. But beyond the mayhem are artsy and ethnic neighborhoods, beautiful parks and the expansive shores of Lake Michigan. Civic and ethnic pride reigns supreme.
The Windy City is home to the world's largest Polish population outside of Warsaw, and famously dyes the Chicago River green each year in celebration of St. Patrick's Day. Visitors are often surprised to find this big, brash city a very friendly place. You're almost guaranteed to discover, as in the song, that Chicago is your "kind of town."
What to See
 Millennium Park is 24.5 acres and right downtown (on Michigan between Randolph and Monroe Streets) on land previously owned by the Illinois Central Railroad. World-class music, art, architecture and gardens merge here. On warm, sunny days, kids soak in an interactive fountain designed by artist Jaume Plensa of Barcelona, which features two 50-foot-high glass block towers and a reflecting pool.
 Another sculpture, Cloud Gate by British artist Anish Kapoor, draws crowds who come to look at the elliptical reflection of the skyline in the jellybean-shaped sculpture's polished stainless steel (it's gained the nickname "the Bean"). In winter there's ice skating, while warmer weather brings free concerts at the Jay Pritzker Pavilion, designed by Frank Gehry.
There are many tours of Chicago's must-see architectural sights, but your best bet is those offered by the Chicago Architecture Foundation. There are guided tours by bus and on foot, but our favorites are the boat tours on the Chicago River (offered late April to November) for a unique perspective on structures like the 90-acre Merchandise Mart, which was usurped by the Pentagon as the world's largest building. You can go the self-guided route by purchasing a detailed map at the CAF's headquarters in the historic Railway Exchange Building (224 S. Michigan Avenue), where you'll also find an excellent gift shop.
Families and nature lovers won't want to miss a visit to the John G. Shedd Aquarium (1200 S. Lake Shore Drive), which with its recently renovated Oceanarium (a massive marine mammal pavilion) now has the world's largest indoor collection of aquatic mammals, reptiles, amphibians, invertebrates and fish. Permanent exhibits at the Shedd include the kid-friendly Polar Play Zone and the Wild Reef, where floor-to-ceiling windows let you view sharks, stingrays, eels and more.
Chicago's most famous resident is now living in Washington D.C., but you can still check out President Barack Obama's favorite Windy City haunts with a self-guided itinerary from the Chicago Convention & Tourism Bureau. The three-day Hail to the Chief's Favorites itinerary includes stops at the University of Chicago (where Obama was a law professor for 12 years), Grant Park (the site of Obama's Election Night rally) and several of the Obamas' favorite restaurants.
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