When you think of Chicago and picture an image of the city– you probably think of the Mafia Mobsters, bootlegging, jazz clubs and the ‘Roaring Twenties’ and think that today it probably has a hangover from those times.
Chicago certainly has a history from those times, and the bars and Jazz clubs are still here, but Chicago has also evolved into a City with pride in its past and also its future, with a diverse cultural mix of people from all over the world.  
Chicago has a population of about 2.7 million people, making it the third biggest city in the USA after New York and Los Angeles, and its main airport, O’Hare one of the busiest airports in the world. Midway Airport is also very busy too.
What surprises many people coming to Chicago, often called “The Windy City” is what a stylish city Chicago is, with lots of classic Architecture, wide streets in the center of the city, lots of parklands and a great location next to Lake Michigan. There are a large number of parks and gardens throughout the City, and you can feel a sense of space when you are here, which really adds to the ambience and enjoyment of the City.
They call it the “Windy City” not because of the cold winds that can blow straight through you, but according to locals – the City was and is such a great city, that locals always “talked big” and boasted about how great the city is! Maybe this is fact, maybe fiction!
When you fly into Chicago, the first thing you notice is the massive grid pattern of street blocks that are laid out below you – a City plan that dates back to 1830. You will also see the number of aircraft lined up on runways to take off with more aircraft also lining up ready to land too. O’Hare is certainly one of the busiest airports in the world, but it is easy to navigate too – with Shuttle buses to hotels, taxis and also a train service to the City center, to the area known as “The loop”. It can however take sometimes close to an hour to get to the city center due to traffic.
THE CITY of Chicago is located in the Mid-West of the USA on Lake Michigan, and the area was originally occupied by Potawatomi Indians, with early French fur hunters and traders coming to the area in the late 1700’s, followed by Jesuit missionaries, military posts, new settlers and Yankees heading from the east coast from Boston and New York seeking to make a new life by establishing farms and other enterprises in the mid-west.
As more new immigrants headed from the East Coast inland and established their homes and farms, the need to transport goods to and from the area also grew, with early transport being either on foot or on horse, with bigger freight and goods transported by boat, and then by the mid 1800’s by railroad.
Chicago became a hub for transport and for trade in wheat, corn, hogs, timber and cattle, and as this trade developed, so too did its industrial base too – with steel mills being built along the Calumet River in Chicago along with grain elevators, meat processing and other industry spreading out across the city. The City very quickly became a center for industry and trade.
The Erie Canal, opened in 1825, linked the Great Lakes and Buffalo to the Hudson River and on to New York, and in 1848 the Illinois and Michigan Canal linked the Great Lakes and Chicago to the Mississippi River and basin building Chicago’s fortunes in the process.
Much of the area on the side of Lake Michigan was swampy, and with rapidly growing numbers of horses and wagons making the streets more a muddy bog than a roadway. To overcome this problem a number of sidewalks and some of the roadway areas were built in wood to get above the mud. This however had an unintended consequence, as wood could also catch fire.
In 1871 the Great Chicago Fire burnt half the entire city to the ground with some 18,000 buildings destroyed and 300 people losing their lives. For many cities this would have been the end of the City, but for Chicago it was the start of a new era and building boom.
The burnt remnants of the buildings were used as land fill, and with new Fire regulations in place – Chicago began to be rebuilt. The Chicago Water Tower on Michigan Avenue dates back to 1871 and is one of the only buildings in the center of the City to survive the fire. This is now the main Chicago Visitor Center and located at 177 E. Randolph Street. It is also a landmark that stands out, and a must see for visitors. All of the land area between Michigan Avenue and Lake Michigan is reclaimed land – with the remains of the burnt city used as part of the land fill.
With the rebuilding of the City, the opportunity to develop new parks, foreshore areas, housing, commercial and industrial buildings presented itself, and by the 1880’s Chicago’s economic wealth had attracted a number of architects and designers to the City including Frank Lloyd Wright (1867-1959) who joined an architectural firm, ‘Adler and Sullivan’ in Chicago, whose principal architect was Louis Sullivan (1856-1924) and his architect/engineering partner, Dankmar Adler (1844-1900).
In 1893 however Frank Lloyd Wright left the firm to start his own practice. Over coming decades, Frank Lloyd Wright completed the design of over 1100 buildings of various types and construction, with around half of these plans becoming buildings, both in the USA and abroad. He also went on to lecture, write, tour and influence American design and architecture in all its forms.
The ‘Chicago School of Architecture’ and what became known as the “Prairie Style” of architecture were born in the process, and today some of the best City tours are architectural tours in and around the Loop and city center, the Oak Park district, near the University and by cruise boat on the north and south branch of the Chicago River in the City. While many of the buildings you see on these Chicago tours were not designed by Frank Lloyd Wright, his design ideas and influence, and those of his fellow architects can be seen throughout the city of Chicago and in the creation of the ‘Chicago School of Architecture’. You can however see and take tours of Frank Lloyd Wright’s home and studio at 951 Chicago Avenue in Oak Park. (See Tel: 312 994 4000).
The world’s first skyscrapers were born during this period, with William Le Baron Jenney (1832-1907) designing the first skyscraper using steel and other architects following on with the use of stone, glass and other materials that can still be seen in many of the City’s buildings. There is a Skyscraper Museum, but this is in New York – but to read more about skyscrapers, see
As Chicago grew as a city, so too did its industry, and the Chicago Board of Trade, (CBOT) incorporated in 1848 was perhaps the forerunner of new service industries that would follow. The Chicago Stock Exchange began operation in 1882 and companies like Sears Roebuck developed their retail empire. The birth of the ‘Department Store’ started here in Chicago, as did refrigerated transport of meat and other perishables.
Between the 1830’s and 1865, when Slavery was abolished at the end of the Civil War, Chicago became a part of the “Underground Railroad” where runaway slaves from southern states headed north to get to Canada and freedom, moving from safe house to safe house as they moved northwards. More than 100,000 slaves headed to freedom on the “Underground Railroad” with Chicago forming an important part in this. Harbouring an escaping slave however was not without its perils, and in 1850 the “Fugitive Slave Act” imposed a fine of $1000 on those found harbouring a slave.
In 1869 the Trans Continental Railway was completed linking the East Coast of the USA to the west coast. Workers including many Chinese workers worked to build the railway, and with its completion many ended up heading to live and work in Chicago. Chicago’s Chinatown (centered around Wentworth and Cemak Streets) dates back to this time. The population of Chicago grew rapidly and by 1900 the population of the city reached 1.7 million people, many attracted to work in factories and the steel industries and others to work in the city in banking, insurance, trade, education, newspapers, advertising and other industries.  
Prohibition began in 1919 in the United States, a law that prohibited the sale and consumption of alcohol, and this law established a new industry, “bootlegging” – a term based on the old practice of hiding alcohol in a boot to hide it from observation and the word “speakeasy” as a name for the bars that operated in and around Chicago. A new chapter in Chicago’s history began at this time – as the City came under the control of Mafia crime gangs and their leaders, the most notorious of these being headed by Al Capone (1899-1947).
The ‘Chicago Outfit’ had been operating in prostitution, extortion and other crimes since the early 1900’s, but prohibition led them into bootlegging and greater violence using intimidation and guns to shoot and kill their opponents. Chicago during the 1920’and 1930’s gained a reputation as a Mafia stronghold. Al Capone in 1932 was arrested by the FBI and convicted on Tax fraud charges, and there have been lots of movies and TV storylines written around Chicago, Al Capone and its mafia years.
In what became known as ‘the roaring twenties’, Speakeasy bars and clubs became a big part of the Chicago scene, with Jazz players and bands making Chicago a center for Jazz, Blues and dance.
A second production plant was built in Chicago by the Ford Motor Company to produce the Model T in 1924 and the Model A followed in 1928. The age of automobiles had arrived and with it the growth in roads, highways and the spread of suburbia.
While the early part of the twentieth century was a boom time for industrialisation, since the 1960’s it has been in a state of decline, with steel works closing down and the big numbers of workers in such places being laid off. Chicago has changed in the process, and while long traffic jams and freezing cold winters are still a factor, the city still has a strong educational , business and commercial base and has also become an attractive destination for tourists and travellers, particularly during the summer months when there are lots of activities to draw people to them.
Exhibitions, trade shows and big sporting events are also attracting more people to the city, and the City maintains its position as the gateway to the west, with the famous Route 66 which began construction in 1926 starting in Chicago and heading west to Santa Monica on the coast in California. The original ‘Route 66’ has changed a lot with new highways and bi-passes added, but it remains a strong part of American culture. The USA President, Barack Obama lived in Chicago, and still calls Chicago home, as does Oprah Winfrey, who build Harpo Studios here in Chicago too.
Chicago has grown as a city and is a great city to visit particularly during the summer months, but also in other seasons. There is no doubt that you will enjoy the food, restaurants, parks, hotels, theaters, architecture and the people too.
Welcome to Chicago – one of the great American cities.
Happy Traveling!
Geoff Stuart

Happy Traveller

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