Why it’s my kind of town

Heart pumping and palms sweating, it was time to face one of my biggest fears. Vertigo had taken hold of me as I was about to step out on to “The Ledge”, a balcony made from glass extending four feet outside the 103rd floor of the former Sears Tower.

All that stood between me and a fall to certain death from the “skydeck” of Chicago’s Willis Tower – until 1997 the tallest building in the world – was the transparent material beneath my feet.

Slowly I inched forward, concentrating for all I was worth on the hazy horizon that stretched to neighbouring Michigan and beyond. Stretched out underneath my feet was a breathtaking scene of glass, steel and masonry skyscrapers, punctuated by parks and highways. Off to my left I could just make out the shimmering waters of Lake Michigan and O’Hare International

Before touching down, I had imagined the city to be a rough, slightly seedy industrial town. I couldn’t have been more wrong.

It sure is “migh’dy priddy”, as Doris Day once sang, with clean streets, immaculate parks and beaches, and no shortage of classy shops, especially along the “Magnificent Mile”.

To get up close and personal, I hopped on a hi-tech Segway, becoming one of many people weaving their way around the 24-acre Millennium Park and neighbouring Grant Park next to the waterfront.

Our bubbly host Brittany, from Absolutely Segway Tours, was brilliant at explaining how to ride the machine – a cross between an electric scooter and a pogo stick – but failed to warn me how distracting the sights can be.

Just as I was getting to grips with accelerating and braking, using the balls and heels of my feet, I turned a corner, caught sight of a spectacular waterfall and nearly came to grief on a big stone.

The waterfall, named Buckingham Fountain and modelled after a fountain at Versailles, is surrounded by immaculate gardens and has a wonderful backdrop of the Willis Tower and other skyscrapers that sparkled in the midday sun.

My hat goes off to former Mayor Richard M Daley, who is largely responsible for putting the chic back into Chicago. During his 22-year reign, Daley is said to have looked out at an unsightly parking lot and made up his mind to turn it into the beautiful Millennium Park.

Now, tourists by the million enjoy the open-air concert venue (which converts into an ice rink during winter), the contemporary works of art and the gardens, plus the huge Shedd Aquarium. His zero tolerance to litter was also readily accepted by Chicagoans and has made the city a cleaner, more friendly alternative to its brash, big tourist rival, New York.

One of the best vantage points from which to enjoy the city is with a cocktail or two on the 16th floor of the Trump International Hotel, the second largest building in the city. Outside the aptly named Sixteen Restaurant, there’s The Terrace bar from which to soak up the views of the beautiful Wrigley Building, Tribune Tower and one of old rogue Al Capone’s haunts, which had a lift for his car, to take him to the top floor and escape his enemies back in the roaring Twenties.

As an added treat, throughout the summer, the city puts on firework displays every Saturday and Wednesday night on the coast, and The Terrace enjoys the best view of all. But be sure to book in advance, as the venue is hugely popular with the in-crowd.

It’s the perfect place for an aperitif before a meal at lively Gibson’s Bar & Steakhouse, upmarket Henri or, for a special treat, the Culinary Journey at five-star hotel Peninsula Chicago – my base for the weekend.

To get a real feel for the place, I was invited along to two of the city’s iconic sporting venues, Wrigley Field and Soldier Field.

Sport is the lifeblood of the city, none more so than at ivy-clad Wrigley Field, home of the beloved Chicago Cubs baseball team. If passion and dedication equated to success then the Cubs would win the World Series every year, but it’s no fewer than 102 years since their last triumph – a run that has earned them the tag of Loveable Losers.

I had a ball one sunny afternoon, munching hot dogs, sipping ice-cold beers and singing along with organist Gary Pressy and American families to Take Me Out To The Ball Game and other club songs. And fortunately, I was able to bring them a little luck as they pulled off a rare victory over fellow strugglers Houston Astros, 7-6.

There’s no shortage of sport all year round and if sport is the heartbeat of Chicago, then blues music is its soul. No trip to the city should be made without at least one evening spent foot-tapping at one of the blues bars. I persuaded a friend to join me at Buddy Guy’s Legends, a popular haunt downtown where, for just $10, we enjoyed a terrific band led by Joanna Connor, and a few reasonably priced beers.

To huge cheers, the great Buddy – now a sprightly 75 – appeared for a brief sojourn singing one of my favourites, Feels Like Rain, and Damn Right I’ve Got The Blues. Yet again, the Windy City simply blew me away.

GETTING THERE

Chris Wiltshire flew to Chicago with American Airlines as a guest of the Chicago Convention and Tourism Bureau.

He stayed at the award-winning Peninsula Chicago Hotel.

North America Travel Service offers three nights’ room-only at the Peninsula Chicago, including American Airlines flights from Manchester for £1,090 (two sharing superior room) in November.

North America Travel Service: 0845 122 8899 or visit www.northamericatravelservice.co.uk.

American Airlines reservations: 0844 499 7300 or visit www.aa.com.

Destination information: www.choosechicago.com. Chicago Like A Local blog is at http://chicagolikealocal.com.

To get around when you get there visit Transitchicago.com/visitors, which includes a useful guide and L train and bus maps.