The Windy City. 1.Navy Pier has been a Chicago landmark since it opened in 1916.It now showcases a unique collection of restaurants, shops and plenty of entertainment. At Navy Pier you'll find the Chicago Children's Museum, an IMAX theater, Crystal Gardens (an indoor botanical park), the Chicago Shakespeare Theater and Smith Museum of Stained Glass Windows. 2.The Art Institute of Chicago is one of the world's great art museums, with collections dating from 3,000 B.C. through the present, including famous French Impressionist paintings and drawings; fine and decorative arts from America, Europe, Africa, Asia and Latin America; photography, textiles and architectural works. 3.Explore a world-renowned garden located right in Chicago's backyard. The Chicago Botanical Garden is a 385-acre, living museum features 23 specialty gardens set on a series of islands and lakes. The Garden is always in bloom, featuring year-round exhibits, festivals, tours and special events. 4.Discover Sue, the largest and most complete T. rex ever found! At The Field Museum, you can get a bug's-eye view in Underground Adventure, descend into an Egyptian tomb, watch a glowing lava flow, be dazzled by sparkling gems, come nose-to-nose with the man-eating lions of Tsavo, and learn about the worlds cultures and environments. 5.The Frank Lloyd Wright Home and Studio complex has served as Wright's private residence, studio and architectural laboratory during the first twenty years of his career from 1889 to 1909. The Frank Lloyd Wright Preservation Trust offers guided interior tours of the Home and Studio. 6.At the Chicago Children’s Museum there are hands-on exhibits and new activities daily make every visit unforgettable for toddlers to ten year olds and adults, too! Dig deep in Dinousaur Expedition, try to stay dry in WaterWays, or climb up to the crow's nest on the Kovler Family Climbing Schooner. Little tota have fun, too in Playmaze and Treehouse Trails. 7.The Shedd Aquarium houses the world's largest indoor aquarium offers more than 22,000 aquatic animals from around the world. 8.Perhaps Chicago's most identifiable claim to fame resides in its architecture. In fact, the city is a veritable museum of modern architecture. It is the birthplace of the skyscraper, and its architects have initiated international architectural styles and movements, the most notable being the Chicago School and the Prairie School. The Chicago Architecture Foundation offers tours, and lectures, and lists current exhibits and events. 9.See some of Chicago's world-famous architecture. Take a virtual tour or browse on your own. Learn about the architects who influenced the city's architecture and view their creations. 10.Chicago's football history goes back to the 1930's and the Chicago Bears play at the newly renovated Soldier Field located on the shore of Lake Michigan just south of downtown. 11.The Chicago Bulls and the Chicago Blackhawks play at the United Center which is a tourist stop for those wanting to see a life-sized bronze statue of former Bulls' star Michael Jordan.The Bulls and Blackhawks will not be playing in October but the check out the United Center’s schedule of events. 12.The Chicago Fire, a member of the 10-team soccer league, plays TOYOTA PARK. The Fire will be playing in October. 13.Chicago is truly a baseball town with the Cubs and White Sox playing in town. The Sox will be away during HFSE but the Cubs are home wrapping up their regular season against the Houston Astros! 14.Boat Cruises - Tour Chicago's world-renowned architecture aboard the Architectural River cruise or experience Chicago's rich history on the Historical Lake & River cruise. Boat tours depart daily from River East Plaza, a short walk from Navy Pier. 15.Since 1959, The Second City has established itself as a Chicago landmark and a national treasure. The theatre that launched the careers of such comic greats as John Belushi, Mike Myers, Bill Murray, Gilda Radner, and more offers nightly comedy shows, as well as a variety of other programs and services. 16.Chicago is home to a vital, vast and varied community of theatrical companies, as well as several large independent theaters, where you'll find everything from traveling Broadway megahits to experimental theater, to Chicago's famous improvisational groups that display the wit and humor of the Second City. 17.The rich contrasts of the city are wonderfully reflected in music. At Symphony Center, you'll find the world-famous Chicago Symphony Orchestra, led by musical director Daniel Barenboim. A short stroll will take you to Buddy Guy's Legends nightclub, named for its legendary blues guitarist owner. The blues, jazz, reggae, modern rock and more are alive in Chicago, with dozens of clubs all over town. 18.The 94th-floor observatory, more than 1,000 feet above Chicago at the John Hancock Center, features an open-air Skywalk, the Midwest's highest open-air experience; Sky Tours, which takes you on a personal audio tour of Chicago's incredible sights and remarkable history; Soundscope 3-D "talking" telescopes that speak in four languages and create startling real sound effects; a Chicago history wall; and a theme park-style ticketing area that recreates the construction of the John Hancock Center. 19.No syndicated talk show in television can compare to "The Oprah Winfrey Show's" ratings history. It has been the #1 talk show since 1986. "The Oprah Winfrey Show" has received 34 Emmy Awards, including 9 Emmys for Outstanding Talk Show and 7 Emmys for Outstanding Talk Show Host. 20.Best view of Chicago from one of the world's tallest buildings.The Sears Tower Skydeck offers FREE touch and tell computers featuring Chicago’s landmarks in six languages. 21.Millennium Park is located in the heart of downtown Chicago. It is bordered by Michigan Avenue to the west, Columbus Drive to the east, Randolph Street to the North and Monroe Street to the South.Today, with its unprecedented combination of architecture, monumental sculpture and landscape design, the 24.5 acre Millennium Park has become the crowning achievement for Chicago in the tradition of its original founders. 22.The Magnificent Mile offers 460 stores in eight city blocks. Beyond the Chicago favorites like American Girl, Crate & Barrel and Niketown, choose from delectable restaurants, unique shops and several museums and galleries to round out your day on the mile. 900 North Michigan Shops features Bloomingdale's Fashion department store, with six levels of upscale retailers, including several restaurants, full service salon and spa and a state-of-the-art fitness facility. 23.Water Tower Place at 835 North Michigan Avenue features Marshall Field's, Lord & Taylor and more than 100 popular stores. A unique themed food court and restaurant are also on the mezzanine level. Chicago Place at 700 North Michigan Avenue features Saks Fifth Avenue, over 50 unique stores, a beautiful floral shop and a food court on the scenic eighth floor. 24.Westfield North Bridge is an elegant specialty center anchored by the Midwest flagship Nordstrom. Popular retail stores and innovative restaurants are enclosed in a four-level concourse at 520 North Michigan Avenue. 25.Dining Out - Chicago mainstays like a perfect steak or deep-dish pizza, the city's diverse dining offerings feature everything from ethnic dining to traditional family fare to the hottest new restaurants.