Travel: Chicago, my kind of town

FOR those who enjoy a city break steeped in history, character and culture, Chicago offers a warm welcome, writes Craig Brown.

Most visitors breeze into the Windy City during the warmth of spring and summer, but Chicago’s charms and attractions stretch well beyond the balmy peak season, and a trip in autumn, even well into November, has much to offer that is unique to that time of year.

We arrived just ahead of Thanksgiving, a time when America lets loose with the parades and decorations, and makes sure everyone knows the season of goodwill is upon them. Chicago has its own very special event in the run-up to Thanksgiving. The Lights Festival celebrates the lighting up of the city for Christmas, with a parade of marching bands along its Magnificent Mile – the central shopping strip crammed with every brand and store you could want, including an eye-catching Burberry emporium clad in a massive metallic version of its famous plaid. An evening fireworks display bursts over the riverside, and when we visited, our nostalgia buttons were firmly pressed by a performance from Eighties teen pop sensation Debbie Gibson.

Traders make a special effort for this event, with many staying open late into the evening, and enticing shoppers with special sales as well as handing out hot drinks and chocolate treats. It helps to layer-up if you’re going out for long periods; hats, gloves, thick socks and heavy boots are advisable. Temperatures dip steeply and quickly at this time of year, and a sweater at lunchtime can become less-than-adequate by 4pm when the light starts fading.

At any time of the year, a tour of Chicago’s architectural highlights is an absolute must, since some of the 20th century’s greatest designers left their mark on the city skyline. An ideal way to tour the city and get a sense of its layout is by boarding the Chicago Architecture Foundation’s highlights bus. Stop-offs include Frank Lloyd Wright’s Robie Building and financial district landmark The Rookery, best known, perhaps, for its appearance in 1980s blockbuster The Untouchables. An unscheduled peek at Barack Obama’s family home was also appreciated and the foundation’s shop is a great place to pick up quirky gifts and mementos to take home.

Even our hotel was striking both inside and out. Positioned midway between the Downtown shopping area and some of Chicago’s wonderful museums, the Radisson Blu Aqua has an undulating design giving the impression that its walls are rippling endlessly. With its boutique hotel décor, stylish restaurant and no-request-ignored service, it’s the perfect base from which to explore the city, or to just relax in. A major bonus is that each room comes with its own iPad, which acts as your own little in-house concierge.

The Radisson also overlooks Millennium Park, home to the massive mirrored bean-shaped Cloud Gate, where tourists pose for pictures. Nearby is the amazing Frank Gehry-designed Jay Pritzker Pavilion, used to host free concerts during summer, which seems to have been constructed entirely from curled strips of stainless steel.

Both are beautiful at any time of the year, but to see the Cloud Gate at night, floodlit and covered in a dusting of snow and watch the pavilion slowly turning red to blue under spotlights was particularly special.

In a city full of thoughtfully curated museums, one must-visit is the Art Institute of Chicago, in the city’s Grant Park. Even a brief wander around the newly opened Modern wing brought us face-to-face with such iconic works as Edward Hopper’s Nighthawks, and Grant Wood’s American Gothic, but it also has some of the greatest Impressionist and post-Impressionist paintings in the world.

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Children of the Eighties will also appreciate the museum’s cameo role in the movie Ferris Bueller’s Day Off, although Matthew Broderick’s high schooler could also have had a field day at the nearby Field Museum. The sheer breadth of its natural history exhibits might have required a week off for Ferris.

Its most famous exhibit greets you in the great hall: Sue, the largest, most complete and best-preserved Tyrannosaurus rex fossil yet discovered. Standing 13ft high at the hips and 42ft long, the 67-million-year-old dinosaur gives a true sense of how terrifying the creature would have looked when she was alive.

There are other marvels, including a zoo-sized taxidermy section, and well-presented, entertaining, interactive exhibits that tempt everyone to button-push. We were also beguiled by a temporary exhibit reminiscing about Chicago’s 1893 World’s Fair, where bottles of olive oil were exhibited as exotic curiosities, and Juicy Fruit chewing gum, the Ferris Wheel and ragtime jazz were introduced to America.

Local brewer Herman Joseph Berghoff also sold his German-style beer at the World’s Fair, and trade was so brisk that he opened a café in 1898 to expand the market for it. The city’s oldest restaurant, The Berghoff, is still there and seemed the obvious stop for a spot of lunch. With its massive, illuminated street sign, The Berghoff has that Roaring Twenties feel with lots of heavy wood furniture and brass fittings, serving tasty German-influenced snacks and meals.

In a city synonymous with bootlegging and speakeasies, the Berghoff was the first establishment to own a liquor licence in Chicago after Prohibition.

If you’re looking for other relics of Chicago’s enforced period of abstinence, Liz Garibay offers a vivacious Tales, Taverns and Towns pub crawl, which takes in some of the picturesque Old Town on foot, and allows you to work your way through an afternoon of ales in pubs where Frank Sinatra was a regular and where parts of Batman: The Dark Knight were filmed, and walk streets where Charlie Chaplin made some of his earliest movies.

The Old Town also gave some of Hollywood’s modern funnymen and women the opportunity to cut their comedic teeth at its legendary improv venue, Second City club. Bill Murray, Dan Ackroyd and Tina Fey have all appeared here.

A great place to dig into some imaginative Italian dishes at reasonable prices, and banter with the staff, is Quartino’s, an Italian eatery that is popular with locals. A truffle risotto, the eggplant Parmesan and a duck prosciutto scored highly with our tastebuds.

In a city whose skyline is dominated by skyscrapers, there’s something refreshingly low-tech about the Ernest Hemingway Museum. There are no digital displays or flash tech here, but the explanations accompanying exhibits are informative and interesting. Across the road is Ernest’s birthplace, recreated as a labour of love. Ever wondered what made Ernest’s uncle cry himself to sleep at night? The Hemingway guides are encyclopaedic – right down to how the “no drinking, no smoking” house rule was resolved.

Alas, we had to leave just before Thanksgiving itself but at O’Hare airport there was time for souvenir shopping, and a remarkably good Mexican meal. As travellers flooded in through the arrivals gates to spend the holiday with their families, we couldn’t help but feel a little envious; Chicago, we’ll be blowing back your way soon.

•Aer Lingus flies daily from Glasgow to Chicago, via Dublin airport. Fares start from £265 each way, aerlingus.com; rooms at the Radisson Blu Aqua Hotel start from £115, www.radissonblu.com/aquahotel-chicago; www.choosechicago.com