OF all the cities I have been alone in, New York was the most difficult to love, more of a slow burn than a tumble.

I put a toe in California once. A place called Needles, part of San Bernardino County in the Mojave Desert. It sounds romantic, hot winds blowing and shimmering sands shifting, but it was not. Henry Fonda passed through it in The Grapes of Wrath and I was only pleased it was a real place, and not part of my fevered imagining of America.

That visit was part of a disorganised road trip and, I found out later, if we'd only planned it better we could have gone to the town of Catfish Paradise, which is a regret I must live with.

After Needles, New York was the longest woo. Took a few visits to appreciate what all the fuss was.

Chicago, however, that had me at hello. Chicago in winter is presented as a fearful proposition.

You'll freeze, I'm told. Pack your thermals. The US border guard at Dublin Airport spends a long time questioning me about my tolerance of sub-zero temperatures, forgetting to care about the purpose of my visit.

Friends of friends - now just friends - pick me up at O'Hare and, within minutes, ask why on earth I'm in Chicago in March. The sky is aggressively, perfectly blue and the sun a persistent yellow.

Gently broiling in my heavy coat, I'm wondering how long is polite to wait until I start stripping layers off. It is, in Scottish parlance, taps aff.

Had it been taps oan, though, I wouldn't have cared. To be free again, after so long, and travelling alone abroad is such a privilege.

It's perhaps an only child thing, perhaps just arrogance, but I enjoy my own company and I enjoy it most overseas. I have gone alone to many countries, dozens, and alone I have experienced small kindnesses everywhere. Someone, somewhere, will appear when you need them, whether silly little boost or serious.

In a Chicago coffee shop a girl comes over to say she likes my outfit. "You look cute," her mouth shapes over the music from my headphones.

At the L station I can't buy a rail ticket with my credit card without a corresponding US zip code. A woman gives me her spare Ventra card and loads some money on it.

Your little social bubble is burst. Alone, you speak to more people, some you like, some you don't.

I ask before sharing a lift with anyone, a strange new courtesy, and a young woman replies "I'm not even wearing a mask, so what do you think?" On she adds: "I stupidly went for a vaccine, so we'll see what that does." Indeed we will.

I went on a food tour, because everyone tells you about the food in Chicago. The deep dish pizza, of course, and the invention of the brownie, or so they claim.

The Herald: Chicago postcards

At the other end of the scale, Chicago also stakes claim to the world's first skyscraper, The Home Insurance Building, constructed in 1885 and razed just 46 years later to make way for the Field Building. Food and architecture, the guide tells us of both.

Like many cities built on industry – here, rail and freight and wheat – there is a hard edge matched with an insistence on creative reinvention, and we learn of the music scene too.

At the start of the tour the guide lines us up and asks us to give our names, where we're from and a "dirty food secret". I run through a catalogue of calamity in my head and then settle on this.

"I had been vegetarian," I call up the line,"For about 20 years and then, one evening, I was in Asda, a supermarket, looking, I'm not kidding you, at Quorn sausages, and a staff member sidled up to me and said, 'D'you want a rotisserie chick'n for 50p?'

"I had explained I didn't eat meat but she was persistent and agog that I could knock back a chicken at such a bargain price.

"Not wanting to be rude, I took one.

"The car on the road home was fragranced with roast chicken; I was saturated with it, my hair, my clothes, this primitive, insistent smell.

"I went into my flat and sat on my sofa with the chicken on my knee and I ate the whole thing with my hands. Like an animal."

The woman next to me said, "I'm Sarah, from Wisconsin, and my dirty food secret is potato chips." Next to her: "I'm Linda, from Vancouver, and I like baloney."

Oh, I said. "I misunderstood the assignment." It doesn't matter. Alone, you can be anyone you want to be and sneak off when you choose.

Travelling alone is also an opportunity to catch up on reading, if you're in to that sort of thing.

I have a friend who travels constantly for work. We have an uncanny amount in common but diverge on two main points: horses, and dining alone. He hates them, I adore them.

The key to being alone in a restaurant is reading. I have brought Joan Didion with me. She seems the right sort of companion for this excursion and she keeps me entertained in several restaurants.

The Herald: Cloud Gate

I take Sylvia Plath to a blues club, Buddy Guy's, but even I am not dick enough to read The Bell Jar in a blues club so I have a drink and listen to the music, as you’re supposed to.

Paraiba tourmaline is rarer than diamonds, the gemstone given its unique colour by traces of copper. The edges of Lake Michigan are the exact colour of this precious stone. Nothing to do with minerals, but rather the angle of light as it penetrates the surface of the water.

Further out, where the light pushes in deep, where the reflection is dimmer, the water becomes cobalt.

The entire city is shades of blue. Tall buildings spring up as though someone has run their hand against the nap on a piece of velvet and the glass of these peering great structures reflects the cyan sky and reflects the cornflower water.

Cloud Gate, more reflections of more blues, makes me giddy alongside the other tourists who have come to gawk at this hunk of public art.

I take a long, long walk around the edge of Lake Michigan and see the ice at the edges cracking, its fissures spreading like gossip.

Two plump ducks waddle drunk on the ice and, although the world keeps shifting and splitting and reconfiguring itself, everything is fine watching their webbed feet and the endless blue beyond. A breath in, a breath out, free again as can be.

My friend texts on my return. “How was Chicago?” he asks.

“Good thanks,” I write back. “Really great.”