Have a high old time in Chicago

It’s as famous for its architecture as it is for its history of jazz and finds there’s a lot to love in this ‘big small town’

IT WAS 1.30am. The man in the fedora at the Green Mill had danced all evening, bebop and swing style, to a seven-piece band called the Fat Babies, with partners as stylish as he was. On the way out, now wearing a swaggering overcoat, he pulled his hat over his eyes, executing a little balletic turn around a pillar. Pure Gene Kelly. Then he disappeared into the sub-zero Chicago night. A moment of magic.

The Green Mill Cocktail Lounge in uptown Chicago is as old as jazz – 100 years – and still going strong. It is dark and plush, as a jazz club should be.

Al Capone had a favourite booth. The waitress said her 90-year-old grandad remembered him well.

Was that the moment I fell in love with Chicago? Or was it the first sight of the skyline with Lake Michigan spread out beneath? The word “lake” fools you. You expect to be able to see the other side. No chance. It’s an inland sea.

Or was it the boat trip, the architectural tour, which winds round the Chicago River, the glass and steel skyscrapers rising up on both sides, as though you’re gliding through a glittering, man-made canyon? If you’ve never understood the beauty of skyscrapers you’ll be converted, even though it was bitterly cold and we sat huddled in our coats sipping hot chocolate.

Or maybe it was checking in to the Sheraton Grand in a room on the 29th floor with the sun setting, the lights of the city coming on, a distant siren or two.

The Sheraton is a very grown-up hotel, 1,200 rooms, comfortable and comforting, with wood panelling and tasteful artwork. My room was all glass and thick carpets and a bed as big as Lake Michigan.

Former President Obama was also staying there for one night, having addressed a climate change conference.

Like my room, the presidential suite looks across the river to one of the city’s most wonderful skyscrapers: the 98-storey Trump Tower, completed in 2009 with Trump in 20ft, lit-up letters. Barack must have been thrilled to see that.

Though I’ve no doubt Chicago in the summer is a delight, there is something about winter in the Windy City that has its own charm. The breeze whips off Lake Michigan, the cityscape set against the ice-blue sky is dazzling and skaters swish and stumble along the “ribbon” of ice, the free rink in Maggie Daley Park.

Someone described Chicago to me as a “big small town”. Spot on. You have all the glitz of New York, but go to the top of the famous 110-storey Sears Tower (now renamed Willis Tower) where you can walk on to a glass ledge and stare down to the ground 1,450ft