Chicago is the great American city that visitors from abroad most often overlook, and they are missing the best of the three. It has the museums and the cultural heft of New York with none of the frenzy, a lakefront that puts most coastal cities to shame, and an architectural heritage unmatched anywhere — this is the city that invented the skyscraper and never stopped refining it. It is also a city of neighbourhoods, of deep-dish pizza and blues bars and a civic pride that can be infectious. The nickname “the Windy City” refers, depending on who you ask, to the lake breezes or the politicians; either way, do not let the winters put you off. In the warmer months, Chicago is magnificent.
Chicago is on our list. Somehow we’ve never been able to fly there, include it on a road trip or cycle through it. However the material here is sourced from reliable sites and should help you decide on visiting the city and plans when you’re there.
A Little Background
The land at the mouth of the Chicago River is the traditional homeland of the Council of the Three Fires — the Ojibwe, Odawa, and Potawatomi nations — for whom the portage between the Great Lakes and the Mississippi watershed made this a place of real strategic importance. The name itself derives from a Native word, shikaakwa, for the wild leeks that grew along the river.
The settlement grew from a trading post into a town incorporated in 1837, and its position at the junction of the lakes, the rivers, and later the railroads made it the great hub of the American interior — the city that funnelled the grain, timber, and cattle of the West to the East. In 1871 the Great Chicago Fire destroyed much of the city; the rebuilding that followed, on a grid beside the lake, became the laboratory in which modern architecture was invented, and the steel-framed skyscraper was born here in the 1880s. The city’s stockyards, its industry, and its waves of immigration built the brawny, plural metropolis that Carl Sandburg called “the City of the Big Shoulders.”
What to See and Do
Millennium Park, on the lakefront downtown, is the obvious starting point, and at its centre is Cloud Gate — Anish Kapoor’s vast, mirror-polished sculpture, universally known as “the Bean,” which reflects the skyline and the crowds in equal measure. The park also holds the Frank Gehry-designed Pritzker Pavilion and the Crown Fountain, and it sits beside the green sweep of Grant Park along the water.
The single best way to understand Chicago is the architecture river cruise, run by the Chicago Architecture Center and others: an hour or so on the river with a knowledgeable guide, taking in the skyscrapers from the water. It is the rare tourist activity that lives up to every word of its billing. For art, the Art Institute of Chicago — guarded by its two bronze lions — is one of the greatest museums in the United States, with an Impressionist collection rivalling anything outside Paris and American icons like American Gothic and Nighthawks.
For the view, the Willis Tower (still “the Sears Tower” to locals) and the 360 Chicago observation deck at the John Hancock building both offer glass ledges and dizzying panoramas. The lakefront itself — beaches, the long trail, Navy Pier — is the city’s great democratic space, kept free of building by a nineteenth-century decision to leave it “forever open.” And the food is a serious business: deep-dish pizza is the cliché, but the city’s neighbourhood restaurants and its blues and jazz clubs are the deeper reward.
Getting There
Chicago has two airports: the vast O’Hare International, one of the busiest in the world and a major global hub, and the smaller, closer Midway. Both connect to downtown by the ‘L’ — the elevated rapid-transit system that is itself part of the city’s character. Chicago has the best public transport of any American city outside New York: the ‘L’ and the buses cover the city well, and downtown (the Loop) and the lakefront are very walkable. A car is unnecessary and a nuisance.
Weather
Chicago has a continental climate of genuine extremes. Summers (June–August) are warm to hot and are when the city is at its glorious best — festivals, beaches, baseball, the lakefront in full use. Late spring and early autumn are pleasant. Winters are long, cold, and famously brutal when the wind comes off the lake — atmospheric, but not for the unprepared. Come between May and October for the best of it.
The Bottom Line
Mid-range hotels run roughly US$180–330 a night, higher in peak summer and during big conventions. Three days covers the park, the river cruise, the Art Institute, and a couple of neighbourhoods; the city rewards a fourth. Of all America’s big cities, Chicago is the one most consistently underrated by international visitors — go, and you will wonder why you waited.