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.

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 over 2000 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.

Despite burning to the ground in 1871, Chicago boomed thereafter, doubling in population every decade and by 1900 the city was home to over 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 willing and not averse to strenuous physical labour and largely monotonous tasks. 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 Bugsy 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 Daley – father of the present mayor – who ran Chicago single-handedly from the 1950s until his death in 1976. These days, the tourist authorities play down the mobster era; few traces of the hoodlum years exist, and those that do owe more to Hollywood than contemporary Chicago.

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 to the 110-storey Willis Tower (more commonly known by its former name, Sears Tower). The city is rightfully quite proud of its vast number of places to visit; including the wonderful new Millennium Park and the extraordinary treasures of the Art Institute of Chicago, as well as several other excellent museums, along with restaurants, sports and highbrow cultural activities. One such cultural activity of note is the raucous and rather funny Second City Theater, which was founded in 1959. Over the years, this improvisational comedy training ground has served as the incubator for talents such as Stephen Colbert, Tina Fey, John Belushi and Chris Farley. Perhaps its strongest suit, however, 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 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. Two great ways to get a real feel for the city are to head out to ivy-covered Wrigley Field on a sunny summer afternoon to catch baseball’s Cubs in action, or take one of the Wendella Cruise Boats under the bridges of the Chicago River at sunset.