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Three Days in the Windy City
By Laura Newsome

A city characterized by canyons of steel skyscrapers, gilded archways, stone pediments and soaring train tracks, the Windy City is the birthplace of the skyscraper, the Chicago blues and some of the most innovative architecture ever created in America. Neighboring the icy landscapes and serene beauty of Great Lake Michigan, waves of immigrants came from all over the world to claim Chicago as their own, transforming the Windy City into a distinctly American metropolis.

Although the great fire of 1871 leveled most of the city, Chicago residents saw the tragedy as an invitation to build their city even higher, creating a soaring and distinctive skyline where each building stands as both an architectural achievement and a work of art.

Day One: Downtown's Staley Skyscrapers
A proper tour of the Windy City begins with a birds-eye view from the towering vantage point of its signature landmark—the 1,454-foot Sears Tower. Hop on an elevator that travels a dizzying 1,600 feet per minute to the sky deck on the 103rd floor, which offers spectacular views of Chicago’s waters and gilded skyline. Bordered by the Chicago River and Lake Michigan, downtown Chicago is encircled by The Loop, a network of elevated train tracks that surround the city’s signature skyscrapers and bustling financial district. The Loop is home to a number of famous buildings, including The Rookery, famous for its gold and marble-columned light court lobby, designed by Chicago’s favorite son, Frank Lloyd Wright.

Further down Adams Street is the Marquette Building, one of the best examples of Chicago School architecture, while the Auditorium Building, done in a Richardson Romanesque-style, houses the magnificent Auditorium Theatre, adorned with elliptical arches, gold-leaf plaster and onyx detailing. For a more in-depth look at Chicago’s skyline, visit the Chicago Architecture Center housed in the porthole-lined Santa Fe Building.

For a pleasant afternoon stroll, buy a famous Chicago hotdog and take a walk along Dearborn Street and Randolph Street to view Chicago’s magnificent outdoor art gallery, with sculptures like Lorado Taft’s “Fountain of the Great Lakes” and Alexander Calder’s dramatic “Flamingo.” The nearby Art Institute of Chicago is home to Grant Wood’s famous “American Gothic,” as well as signature works by masters like Rembrandt, Van Gogh, Picasso and Chagall. The bedrock of the Chicago business community, the Marshall Field and Company building is a famous store that occupies a city block, noted for its creative window displays and the largest piece of Tiffany-designed glass mosaic in the world.

Millennium Park is a great place to stop for an afternoon snack and a view of 333 Wacker Drive, a curved postmodern building treated with a reflective glass that beautifully reflects the changing shades and shadows of the city skyline. For a stately dinner, visit the ?100-year-old Berghoff restaurant, which serves up fine dishes amid a decidedly Chicago atmosphere of dark wood and rich lighting. After dinner, take in a performance at the glittering Chicago Theatre, a restored 1920s Beaux-Arts theater with an opulent interior adorned with colorful frescos and ornate moldings.

Day Two: The Stylish North Side
Just north of the Chicago River, the city’s stylish North Side was originally populated by Irish, Swedish and German immigrants in the 1880s, and is now home to some of the city’s most upscale residential, shopping and entertainment districts. Chicago’s Michigan Avenue, also known as the Magnificent Mile, is the city’s most fashionable street, and home to the skyscraper that chewing gum built, the shimmering Wrigley Building, and the Tribune Tower, a beautiful gothic skyscraper and home to the Chicago Tribune.

The nearby Water Tower and Pumping Station is one of the few buildings to survive Chicago’s massive 1871 fire. Built in 1866, this gothic-designed limestone structure is now home to the Lookingglass Theatre, and still pumps 250 million gallons of water a day. One of the most distinctive features of the Chicago skyline is the John Hancock Center, 100 floors of glass and steel that features the city’s only open-air skywalk, 1,000 feet above the city streets. The upscale Oak Street is home to designer shops like Armani, Hermes and Versace, as well as art galleries that sell vintage and limited edition posters and prints. Works by contemporary greats like Andy Warhol and René Magritte are on display at the Museum of Contemporary Art, while the Navy Pier is popular for its waterscapes, crystal gardens, Ferris wheel and old-fashioned carousel.

For some signature seafood and a spot of afternoon tea, stop by The Cape Cod Room at the Drake House, a 1920s luxury hotel with red carpets and grand chandeliers. Near the giant corncob shaped Marina City buildings, the River North Gallery District is the largest collection of galleries outside of New York City, famous for its home furnishings and antique shops. After visiting the city’s stunning St. James Episcopal Cathedral and St. Michael’s Church, stop by Crilly Court for a unique glimpse of Queen Anne Chicago-style row houses, complete with turrets, porches and irregular rooflines. The impressive Richardson Romanesque-style Newberry Library houses a priceless collection of manuscripts, including first editions of Dante’s 1481 Divine Comedy and Milton’s Paradise Lost.
v For a taste of Chicago’s storied tycoon era, Astor Street offers a rare glimpse of Chicago’s Gold Coast, a playground of the rich for more than 100 years. Named after the wealthy real estate magnate John Jacob Astor, the street that bears his name features opulent homes like the art deco Edward P. Russell House and 1500 North Astor Street, a palatial Italian renaissance estate. Oak Street Beach is the perfect place for a sunset stroll along Chicago’s lengthy lakefront, which provides spectacular views of Lake Michigan and the city’s Gold Coast skyline. For some fine continental dining, don a jacket and visit the opulent Pump Room, for a night of lively jazz under crystal chandeliers.

Day Three: Eclectic South ?Side Sights
More than 30 years ago, the rundown warehouses and storefronts of Chicago’s South Loop began transforming into artsy lofts and chic boutiques. One of the highlights of this booming area is the Chicago Public Library, Harold Washington Library Center, the largest public library in the world, with a Greek-inspired façade that houses more than seven million books on 70 miles of shelving. To pick up a travel guide or books by local authors, visit Sandmeyer’s Bookstore located in the historic Printing House Row Historic District. Then spend a few hours at the Field Museum, where visitors can view everything from a Mammoth-bone hut to the most complete T-Rex skeleton ever found.

For an early lunch, stop by the colorful bakeries and restaurants of Chicago’s Chinatown, and take a quick stroll to Chicago’s fabled Grant Park—a perfect place to relax beside the beautiful Buckingham Fountain and its four sculpted seahorses. For more views of the water, visit the John G. Shedd Aquarium, which faces Lake Michigan and houses more than 8,000 animals, including Harbor Seals and Beluga Whales. Other must-see attractions include the Adler Planetarium and Astronomy Museum, with its simulated space walk and walk-in planetarium, and the Museum of Science and Industry, a tribute to 20th century technology, with exhibits on jetliners and the Apollo 8 mission.

Once a playground for the wealthy, Chicago’s South Side has experienced an urban renaissance at the hands of the neighboring University of Chicago, whose Prairie School homes and planned green spaces typify the area. The birthplace of many giants of the architecture world, the university has many spectacular sights, including the Robie House, Frank Lloyd Wright’s quintessential Prairie School monument. The area’s unique designs spill over into the stylish suburban neighborhoods of Kenwood and Jackson Park, just a stone’s throw from Washington Park and Hyde Park, two scenic green spaces designed by renowned landscape architects Frederick Law Olmstead and Calvert Vaux.

Farther afield, explore the county’s oldest free public zoo, the Lincoln Park Zoo, and the Brookfield Zoo, one of the largest in the U.S. Nearby Wrigley Field is a must-see for Chicago Cubs fans, and the Pullman Historic District—one of the best-preserved 19th century communities—transports visitors back in time. Explore Oak Park, the birthplace of Ernest Hemingway and the lifelong home of Frank Lloyd Wright, whose signature Prairie School style is evident in many of the buildings in the neighborhood. The eclectic Lower West Side is the perfect place to sample a dinner full of ethnic flavor, while the trendy Wicker Park offers a full array of evening entertainment—from bars and theaters to concert halls and other well-known cultural haunts—this up-and-coming neighborhood is a perfect ending to three days well spent in the Windy City.