A wonderful long weekend in the Windy City with American Sky

Savouring the home of deep-dish pizzas

I’m used to picking up pizzas from the supermarket freezer cabinet or as an occasional treat from the local takeaway, where they come in light portable boxes, so it’s certainly a surprise to see a small team of wait staff surround us and set up circular folding tables.

Chicago pizzaBut when in Chicago do as the Chicagoans do, and we’ve just ordered the classic deep-dish pizza topped with sausages at Lou Malnati’s, the historic home of Italy’s most famous culinary export. As couple of us are vegetarians we’ve ordered a non-carnivorous option for good measure. Before long the waiters and waitresses return to the table; it takes two of them to carry each of the pizzas in heavy dark pans. Welcome to the world of the real deep pan pizza.

A rite of passage on any trip to Chicago, I now realise my ones back home are decidedly lightweight. Indeed, I’m feeling the same when I can barely finish two slices of Lou Malnati’s trademark pizza made with a buttery crust, Mozzarella cheese and vibrant red vine-ripened tomatoes from California. Lou started working in the city’s first pizzeria in the 1940s before opening his own restaurant in 1971, which remains family-run today.

It’s a fun introduction to a city which definitely has its own take on things. We’re in town at the start of a trip to the Great Lakes region along a section of Route 66 which begins in Illinois, the state where Chicago is the largest city. However, it’s also a fantastic destination for a short break, particularly for anyone who has ‘done’ New York, Orlando, San Francisco and other popular US cities.

View from SkyDeckWhen it comes to first impressions you can’t miss the distinctive skyline and one of the best places to see it is from the SkyDeck where you can ‘step outside’ the tallest building in the Western Hemisphere at a height of 1,353ft. The attraction is on the 103rd floor of the former Sears Tower, which now goes under the name of the Willis Tower. The views through the windows are fantastic enough, but for the ultimate sightseeing thrill you can step out onto The Ledge, a series of glass boxes that extend more than four feet from the side of the building. On a clear day you can see four states – Illinois, Indiana, Wisconsin and Michigan – and it is, quite literally, breath-taking.

If you haven’t got a head for heights you can still admire the skyline from a less vertiginous perspective. The Chicago Architecture Foundation was founded in 1966 to save the historic Glessner House, which marked a radical departure from traditional Victorian architecture, and is now one of the city’s largest cultural organisations.

Chicago cityscapeThe interactive model of Chicago is one of the main attractions, with than 4,000 miniature buildings telling the story of a city that has reinvented itself many times in its relatively short history.

Founded in 1837, connections to inland waterways and railroad networks positioned Chicago as a transportation hub for the entire nation. Our guide tells us that as the United States modernised in the 19th century Chicago kept itself ahead of the game with ground-breaking solutions for buildings and infrastructure, even more so when the catastrophic fire of 1871, which started in one of the wooden buildings of the time, destroyed more than three square miles of the city. This lead Chicago to be the first American city to grow upwards, with the world’s first skyscraper built in 1885; a fact that surprised several of us who assumed New York took the accolade. There’s even a raised train network, called the L line, which is short for elevated.

Chicago river cruiseThe Chicago River remains a focal point of life today and we set off on a 90-minute boat tour. From the big-name Trump Tower which needs little introduction and Wrigley Building built by the chewing gum magnate, to the wave-like balconies of the modern Aqua structure and neo-Gothic grandeur of the Tribune Building, it’s a fascinating cruise through architectural history from 1890 to the present. Another misconception is corrected when we learn that the Windy City didn’t earn its moniker from the weather. It originally derived from the scorn heaped on early politicians who were said to be full of hot air.

The bean in Millennium ParkBack on dry land we visit Millennium Park to see ‘the bean’, a futuristic silver sculpture by British artist Anish Kapoor with the official name Cloud Gate, not that anybody seems to call it that.  Despite its size, Chicago is a very walkable city with many attractions to be found in and around the Magnificent Mile which starts at the river and runs along a section of Michigan Avenue.

Here, after a bit of searching, we find another Chicago dining institution, the Billy Goat Tavern & Grill. Tucked on a lower level beneath the grand boulevard, it’s a world away from some of the fancy restaurants nearby and great fun. It was founded by another enterprising immigrant, in this case William Sianis from Greece, who opened his original Lincoln Tavern in 1934 and renamed it after a goat somewhat incongruously fell off a passing truck, wandered inside and found itself a new home. Resembling an old-fashioned diner, the mainstay on the short and inexpensive menu is the ‘cheezborger’, served in paper, with cheese and dill pickle. Don’t ask for lettuce or tomato or you’ll be told the goat ate them. And if you want chips you’ll have to make do with the American version – a packet of crisps.

Afterwards we make tracks to our base at the Omni Hotel, which occupies a central spot on the Magnificent Mile, and it’s tempting to go straight to the cocktail happy hour which starts at 3pm and extends to a generous 7pm.

Kingston MinesIf you’ve got the energy Chicago can provide the entertainment, with a nightlife scene that includes around 100 theatres, including the landmark Chicago Theatre, along with live music venues open every night of the week. We decide to take a cab go the city’s North Side, which is home to Kingston Mines, the largest and oldest continuously operating blues club in the city with two live stages. On Saturday night it’s open from 7pm to 4.45am, with a very reasonable entry fee of $15 for all those hours of music. Unfortunately, like the deep dish pizza, we had to admit defeat and went to bed well before closing time. Nevertheless, it was another great experience in a city that’s full of surprises.

More information

American Sky offers a three-night break at the Omni Hotel Chicago from £629 per person, based on two sharing a room and including flights. To book or for more information call 01342 331798. For information on Chicago and the Great Lakes region visit www.greatlakesusa.co.uk.

Silver Travel Advisor recommends American Sky.

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Jeannine Williamson

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