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‘God I love it here,’ she said. ‘I love being here.’

‘What do you mean?’ I said.

‘When you’re here, you know exactly where you are on the planet.’

I thought, Oh my goodness, so you do. It was absolutely true. Since then, I’ve become more and more aware of how iconic landmarks could do that to you – let you know exactly where you were on earth. The Taj Mahal did it. The Empire State Building did it. The Houses of Parliament and the Eiffel Tower did it. And so did the Sears Tower. Most of the time we didn’t know precisely where we were, but those buildings made us totally aware of our place in the world. It was no big deal, just a wee jolly, but it pleased me no end.

Before leaving the tower, I looked out one last time from the roof and gazed southwest. Seeing my journey laid out in front of me got me thinking of what lay further along the road – Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California, then the Pacific. Far below, I could see the thick artery of eight lanes of Interstate 55 snaking through the conurbation – the most popular way out of Chicago. Since the mid-1960s, it had been the official replacement for Route 66. As I mused about starting the journey, I heard the whine of a train horn in the distance. The loneliest sound in the world, but also one of the most romantic, it beckoned me to venture out into the vast plains of America and explore what lay along the mythical highway. But first I wanted to go on another quick spin around central Chicago, one of my favourite cities.

Whenever I’m in Chicago, I make a point of visiting Fort Dearborn. Nowadays it’s just some brass plates on the road and pavement outside Fanny Mae’s sweet shop on the corner of two city centre streets. I always stop in the shop to buy a few sweeties. They do a lovely plain chocolate caramel. If I could force one through the pages of this book, I’d give you one. Those brass plates mark the point where Fort Dearborn used to be located. For some unfathomable reason, I’ve always had a romantic image of the fort, which I used to think was the site of the last Indian battle on American soil. But I recently discovered that it was actually the site of a massacre of French pioneers conducted by Native Americans, supported by the British.

In the 1670s, French pioneers were the first Europeans to travel along the Chicago River. They settled near its mouth and claimed a large surrounding territory for France. About thirty years later, they were driven out by Fox Indians during the Fox Wars, which continued until the 1730s. At the end of the French and Indian War (the North American portion of the Seven Years War between Britain and France) in 1763, the area was ceded to Britain, which in turn lost it to the United States at the end of the American War of Independence. As a result, in 1776 the mouth of the Chicago River was resettled by a new wave of pioneers. Among them was Jean Baptiste Point du Sable, a Haitian farmer and trader who, as the first permanent resident of Chicago, is regarded as the founder of the city. (In case you were wondering, the city takes its name from shikaakwa, the Miami–Illinois Indian word for the stinky, leek-like vegetables that can still be found rotting along the banks of the Chicago River.)

In 1804 US troops constructed a log fort at the mouth of the river. They named it after Henry Dearborn, the Secretary of War, and a small settlement grew around it. The village didn’t last long, though. In 1812 war broke out again between the United States and the British Empire, including Canada. General William Hull, the Governor of Michigan, ordered the evacuation of Fort Dearborn, but Potawatomi Indians ambushed the evacuees, killing eighty-six and capturing sixty-two soldiers, women and children, among them the commandant and his wife, who were ransomed to the British. A posse of five hundred Indians was sent to do the gig, so it was not a small skirmish. Those troops and pioneers got wellied,