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Chicago Travel Guide

Chicago is stereotypically perceived by many as a city of hard-working, blue-collar meatpackers who worship their sports and are addicted to their all-round beef hot dogs and deep-dish pizzas; as a city of unbearable wind braced by warehouses and factories spewing industrial smoke; and as an urban enclave whose streets are terrorized by gun-wielding mobsters and whose offices are run by corrupt politicians.

Chicago, however, has gotten rid of much of this former image. Just as it burst onto the North American scene in the 19th century, transforming from a river side village of 340 into the second largest city in the U.S., Chicago in recent decades has reinvented itself. While it is still the “Windy City” with cold gusts breezing off of its Lake Michigan, still the “City of Big Shoulders” with its towering skyscrapers, and still the city that is home to sports worshippers and hotdog and pizza lovers, its streets and dirty politics has long been cleaned up. And its economy no longer relies on meatpacking or heavy industries but is more service-oriented, diversifying into information technology, finance, communications, and scientific research and development. Moreover, Chicago has become an ethnically diverse city, sophisticatedly cradling fashionable shops and cutting-edge boutiques along with world-class museums and leading academic institutions. And it has become a center of high culture, fostering music and arts and hosting year-round festivals, parades and exhibitions as well as programmes dedicated to theatre and dance.

Still, what attracts most tourists to Chicago is its sheer beauty – both natural and man-made. Chicago’s architecture is simply stunning. Having ushered in the skyscraper era in 1885 with the building of the world’s first steel-framed high rise, Chicago today has one of the most beautiful skylines found anywhere. The city boasts various styles from 1890s era buildings to stark mid-20th century International styles like the Sears Tower, which is also the world’s tallest building. But while its architecture is certainly impressive, it is easy to forget sometimes that a big city like Chicago has some incredible natural attractions; its Lake Michigan, for instance, besides being a gorgeous “Great Lake” used for sailing, yachting, and boating during the summer months is lined with stretches of public parks where locals congregate during the summer months and participate in beach volleyball, picnics, and kite-flying. More green space can be found in downtown with the Millennium Park and Grant Park, and in the north with Lincoln Park. Especially when the sun is out, these urban playgrounds are packed with leisure strollers and serious joggers.

Home to 9.5 million people in its metropolitan area, Chicago sprawls north, south, and west into suburbs for miles. Much of the city is flat, with very few hills, so walking from place to place is made easier.

Chicago also sits strategically along the southwestern shores of Lake Michigan with the Chicago River streaming through the heart of its downtown and connecting with the Illinois River in the south; this has made Chicago a natural hub, as goods from New York can be transported up the Hudson River, connecting with the Great Lakes, and then reaching Chicago where it can be transported via the Mississippi River to interior cities like St. Louis, Memphis, and New Orleans. Chicago is also the crossroads of numerous interstate highways and its airport remains the busiest in the country, a hub for hundreds of connecting airlines.

Chicago is very cold and windy during the winters around 25ºF (-5ºC) while hot and humid during the summers, around 85ºF (30ºC). The same winds that gust off Lake Michigan in the winters make the lakefront the ideal place to be during the summers for a cool-down. In the spring and fall, anything goes. You’ll generally experience cooler than summer temperatures and warmer than winter temperatures, but how much varies and is unpredictable.

Neighborhoods and Districts
There are 77 community areas in Chicago. The city is generally divided unofficially into four sections: Central Chicago, the North Side, South Side, and West Side. Central Chicago encompasses the city’s downtown district and is home to most of the tourist attractions. The heart of downtown is The Loop, which is the elevated train tracks that circle the business and shopping district. The latter is known as “The Magnificent Mile”, which runs one mile between Oak Street Beach and the Chicago River, and is the most popular shopping thoroughfare in Chicago’s downtown.

To the north of downtown is the North Side, where you’ll find wealthy residential neighborhoods Lincoln Park, Old Town, Lakeview, Gold Coast, and Wrigleyville. The city’s clubs, theaters, and the famous baseball stadium Wrigley Field are all located in the North Side.

South of downtown is the South Side, known generally as a more crime and poverty-stricken section but also home to the affluent in some parts. The South Side features neighborhoods like Bridgeport, Bronzeville, Armour Square, Little Village, Hyde Park, Morgan Park, Mount Greenwood, and Beverly. You’ll also find Chinatown, the University of Chicago, and the stadium for the Chicago White Sox here.

West of downtown is the West Side, a region of rehabbed lofts and trendy eateries. You’ll also find ethnic enclaves and hip bars. The neighborhoods of the West Side include Wicker Park, Greektown, Ukrainian Village, Pilsen, Austin, Albany Park, Garfield Park, and Humboldt Park, among others.


Highland Park

Arlington Heights

Oak Lawn

Downers Grove
Glen Ellyn
La Grange
Oak Brook
Oak Park
St. Charles

The Potawatomi Natives were the first to live in the Chicago area. They are believed to have arrived some 10,000 years ago. French missionaries and Canadian explorers ventured into the region in the late 17th century, but did not establish a settlement. After the American Revolution, a settlement was established on Chicago River’s north bank by fur trader Point du Sable. The U.S. government soon afterwards decided it wanted to expand its western frontier by establishing a settlement on Lake Michigan; they set up Fort Dearborn in 1803 on the southern banks of the Chicago River. In 1833, Chicago was incorporated as a town of 340 people, but a real estate boom ensued when construction on the Illinois & Michigan Canal was initiated to connect the Chicago River and the Illinois River, which emptied into the Gulf of Mexico. When the canal was completed in 1848, Chicago became an important town for commercial ships. By waterway, it was connected to New York, the interior of the U.S., and the Caribbean. After a railroad line connecting Chicago and Galena was completed in 1850 and the Illinois Central Railroad started building more tracks south of the city, Chicago soon became the hub of America’s passenger and freight trains and remained so for the next century.

While Chicago’s steel industry prospered during the Civil War, a devastating fire in 1871 broke out killing 300 people and destroying thousands of buildings. The city rebuilt itself, taking advantage of the cleared land to erect skyscrapers. It recovered quickly enough, however, to host the 1893 World’s Columbia Exposition, which drew 27 million visitors during its six-month run and is widely considered one of the most influential fairs ever held; it cemented Chicago’s status as a leading world-class city.

In the 1920s, during the Prohibition era, Chicago developed a reputation for organized crime, centered on illegal distribution of alcohol run by gangsters like Al Capone. Eliot Ness and his federal agents known as “The Untouchables” cracked down on the operations and convicted Capone on tax evasion.

Throughout the early 20th century and into the 1950s, Chicago’s political offices developed a reputation for corruption and engaging in “machine politics”.

While the city suffered a decline in the 1960 and 70s, Chicago has seen many of its impoverished neighborhoods and its downtown districts revitalized in recent years. On the whole, the city is definitely on the upswing.

More than 35 million tourists visit Chicago each year. The city has something for everyone – stunning architecture, historical landmarks, world-class museums, and trendy shopping.

The skyscrapers which Chicago is famous for are all located downtown. Three museums of natural sciences are found at the Museum Campus Chicago, which is a park by the lake that encompasses 58 acres. Be sure to check it out and visit the Field Museum of Natural History, the Adler Planetarium, and the Shedd Aquarium. For upscale shopping, visit the Magnificent Mile – Chicago’s version of the Champs-Elysees.

Art Institute of Chicago
The Art Institute of Chicago is an art museum in the Loop district of downtown and the city’s third most popular attraction. It is most celebrated for its extensive collection of American Art, French impressionist masterpieces, and Post-Impressionist works. Among the highlights of the collection includes three-dozen Claude Monet paintings, Edward Hopper’s Night Hawks, Grant Wood’s American Gothic, and various works by Renoir and Van Gogh. There are also sculptures, including a floor devoted entirely to George F. Harding.

Field Museum of Natural History
The Field Museum of Natural History is the city’s most popular cultural attraction. The museum has an anthropology, geology, zoology, and botany department. The highlight is Sue, the largest known and most complete fossil skeleton of a Tyrannosaurus rex. And along with large collections of other dinosaurs, you’ll find Native American and anthropological artifacts from Ancient Egypt.

Adler Planetarium
The Adler Planetarium is the oldest planetarium in the Western Hemisphere. It was built in 1930. It features exhibits of scaled-down models of stars and the solar system, interactive displays of astronomical interest, and rare, antique astronomical instruments. The planetarium projector can accurately reproduce the night sky and its movement, so check out the regularly scheduled shows.

Shedd Aquarium
The Shedd Aquarium is an indoor aquarium with 25,000 fishes swimming in more than five million gallons of water. At one time, it was the largest indoor aquarium in the world. The aquarium also features mammals, reptiles, amphibians, and insects. Today, it is visited by more than two million people every year.

Museum of Science and Industry
The Museum of Science and Industry is housed in a National Historic Landmark – the only in-place building that has survived from the 1893 World Columbian Exposition. The museum features old relics from the Titanic, a U-505 German submarine that was captured during WWII, British warplanes from WWII, U.S. Navy warships on display, a flight simulator for the F-35 Lightning II, a recreated coal mine, a 3,500 square foot model of a railroad that retells the story of rail travel from Chicago to Seattle, a real Boeing 727 that is part of the “Take Flight” simulated flight from Chicago to San Francisco, the Apollo 8 capsule, and a mockup of a common early 20th century street with old lights and shops and cobbled streets.

Chicago Cultural Center
The Chicago Cultural Center is a landmark of Chicago and is one of the city’s more popular attractions, drawing close to a million visitors each year. It showcases visual, performing, and literary arts and features thousands of programs and exhibitions every year. The building itself is a marvel. Completed in 1898, it stands 105 feet tall and features a famous Tiffany glass dome and thick walls that project mixed Romanesque revival and neoclassical elements.

Navy Pier
The Navy Pier is perhaps the most visited landmark of Chicago, attracting close to 10 million people each year. It is a long pier on the shores of Lake Michigan that was built in 1917 to serve as a cargo warehouse. It was also designed to accommodate passenger steamers. Its use has evolved over the years. The pier grounds encompass 50 acres of parks, gardens, and retail space. Today, it is used a public gathering place, hosting festivals, concerts, and conventions. It is also lined with restaurants, food stands, shops, an IMAX theater, various small museums, art sculptures, a dancing fountain, and the famous 150-foot Ferris Wheel which tourists adore but residents view as an eyesore.

Skyscrapers – Sears Tower, Aon, John Hancock
Chicago’s architecture is a particularly huge draw. The city boasts the Sears Tower, which is the tallest building in the world, the Aon Center, which is the world’s tallest marble-clad building, and the John Hancock Center, which is one of the most celebrated structural expressionist style buildings in the world. The John Hancock also has a distinct X-shaped bracing exterior and two iconic antennae at the top, which if included in the measurements make it the third tallest building in the world.

Auditorium Theatre
The Auditorium Theatre at 50 East Congress Parkway is another one of Chicago’s National Historic Landmarks. It was designed by world-famous architects Dankmar Adler and Louis Sullivan. The theatre is celebrated for its perfect acoustics and rich ornamentation. A number of historic events have occurred in the Auditorium Theatre, including the 1888 Republican National Convention and the Bull Moose Speech of 1912 given by Theodore Roosevelt. The theatre during the 1960s and 70s was used as a concert venue for performances by The Who and Jimi Hendrix. Today, the building houses Roosevelt University.

Wrigley Field
Baseball fans will no doubt want to visit Wrigley Field at 1060 W. Addison Street, not just to catch a Chicago Cubs baseball game, but also to soak in the history linked with this stadium. Built in 1914, Wrigley Field is the second oldest ballpark still in use, behind Boston’s Fenway Park. It is actually the only remaining ballpark that was used for the Federal League, which was the last competitor of the National and American Leagues. One of the most famous moments in baseball occurred in Wrigley Field, when Babe Ruth made a pointed gesture during his at-bat in the 5th inning of Game 3 of the 1932 World Series, as if to call where he was going to hit the ball. In the next pitch, he smoked the ball for a home run, seemingly in the direction of his pointed gesture. The debate lingers on whether the Bambino was predicting where he would hit the ball, or just pointing to the mound to express irritation with the pitcher.

Chicago is famous for its Chicago hot dogs, deep-dish pizzas, Italian Beef sandwiches, and Maxwell Street Polish, which is a bun wrapped around a grilled Polish sausage that is topped with mustard and onions. While not quite on par with its other specialties, Chicago is also noted for its pork-chop sandwiches.

Upscale shopping in Chicago is best done at the Magnificent Mile, in other words the stretch between Oak Street Beach and Chicago River. This promenade features brand name retail shops like Tiffany’s, Louis Vuitton, and Ralph Lauren, mixed in with branded stores like The Gap. You’ll also find indoor malls nearby like the Water Tower Place and Chicago Place. The Water Tower Palace at 835 N. Michigan Avenue has a range of men’s and women’s clothing stores while Chicago Place at 700 N. Michigan Avenue features 45 mixed stores along with a half-dozen restaurants.

There are also boutique shops along Armitage Avenue between Damen Avenue and Halsted Street that sell trendy clothes and beauty products. In Bucktown, along Damen Avenue north of North Avenue, you’ll find more cutting-edge clothes and accessories.

Chinatown, meanwhile, is the place to go for oriental antiques, jewelry, crystal, teapots, and clothes as well as herbal medicines and gift shops.

For souvenirs, head over to the small shops at the Navy Pier, where you’ll find handicrafts, postcards, T-shirts, and items like coffee mugs and key chains.

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