CHICAGO is in many ways the nation’s last great city. Sarah Bernhardt called it “the pulse of America” and, though long eclipsed by Los Angeles as the nation’s second most populous city after New York, Chicago really does have it all, with less hassle and fewer infrastructural problems than its coastal rivals.

Most visitors to Chicago are immediately bowled over by its magnificent urban skyline, adorned with one of the world’s finest assemblages of modern architecture, ranging from Mies van der Rohe’s masterpieces on the campus of the Illinois Institute of Technology to the 110-storey Willis Tower (more commonly known by its former name, Sears Tower). The city is also rightly quite proud of the wonderful Millennium Park and the extraordinary treasures of the Art Institute of Chicago, as well as several other excellent museums. The city’s strongest suit is live music, with a phenomenal array of jazz and blues clubs packed into the back rooms of its amiable bars and cafés. The rock scene is also healthy, having spawned such bands as Smashing Pumpkins and Wilco during the 1990s and R&B stars R. Kelly, Kanye West and Lupe Fiasco in recent years. And almost everything is noticeably less expensive than in other US cities – eating out, for example, costs much less than in New York or LA, but is every bit as good.

Brief history

Founded in the early 1800s, Chicago had a population of just fifty in 1830. Its expansion was triggered first by the opening of the Erie Canal in 1825, and then by the arrival of the first locomotive in 1848; by 1860 it was the largest railroad centre in the world, serving as the main connection between the established East Coast cities and the frontier that stretched more than two thousand miles west to the Pacific Ocean. That position on the sharp edge between civilization and wilderness made it a crucible of innovation. Many aspects of modern life, from skyscrapers to suburbia, had their start, and perhaps their finest expression, here on the shores of Lake Michigan.

The furious pace of development was briefly halted in 1871 when the Great Chicago Fire destroyed much of the urban fabric. Chicago boomed thereafter, doubling in population every decade. The nickname “Windy City” was coined by a New York newspaper editor in the 1890s to describe the boastful claims of the city’s promoters when attempting to lure investors from the eastern United States. By 1900 the city was home to more than two million people, many of whom made their way on crowded ships from Ireland and Eastern Europe. In the early years of the twentieth century, it cemented its reputation as a place of apparently limitless opportunity, with jobs aplenty for those not averse to strenuous physical labour and largely monotonous tasks in factories, stockyards and railroad facilities. The attraction was strongest among blacks from the Deep South: African Americans poured into the city, with more than 75,000 arriving during the war years of 1916–18 alone.

During the Roaring Twenties, Chicago’s self-image as a no-holds-barred free market was pushed to the limit by a new breed of entrepreneur. Criminal syndicates, ruthlessly run by the likes of gangsters such as Al Capone and Bugs Moran, took advantage of Prohibition to sell bootleg alcohol. Shootouts in the street between sharp-suited, Tommy-gun-wielding mobsters were not as common as legend would have it, but the backroom dealing and iron-handed control they pioneered was later perfected by politicians such as former mayor Richard J. Daley who ran Chicago single-handedly from the 1950s until his death in 1976. Today’s mayor, former President Obama staffer Rahm Emanuel, with his slightly abrasive and heavy-handed approach, seems to be continuing the tradition.

  • Wrigley Field
  • Willis Tower
  • Millennium Park
  • The Chicago River
  • The Art Institute of Chicago
  • Lincoln Park
  • Chicago guided tours
  • Chicago spectator sports
  • Accommodation
  • Eating
  • Drinking
  • Nightlife and entertainment