America’s Windy City is the perfect spot for a short break and a slice or two of Chicago deep-dish pizza
There are certain times in life when the only way is up, and this is certainly one of them. My ears pop as the lift floors pass by at seemingly lightning speed and within seconds, I am stepping out on the 103rd floor of Chicago’s Willis Tower.
I’m 1,353ft above ground level on what many people still remember as the Sears Tower, built in 1973 and at the time the tallest building in the world, a title it held for almost 25 years. Today it houses the SkyDeck and offers visitors the breath-taking opportunity to step out onto The Ledge, a three-sided glass box extending outside the tower with a totally transparent floor.
If you’ve got a head for heights this is an extraordinary way to take in the views over the city that’s the largest in Illinois and – on a clear day – enjoy a 50-mile panoramic vista into the surrounding states of Indiana, Wisconsin and Michigan.
It might be known as America’s second city, but there’s certainly nothing second-rate about Chicago, which is a fantastic place for a short break for anyone who has ‘done’ the more obvious US city break destinations and is looking for something different.
Indeed, over the course of the long weekend I learned something new and unexpected on a daily basis. First off, whilst many people associate New York as the birthplace of skyscrapers – as indeed I did – they actually originated in Chicago in 1885. The Home Insurance Building, the so-called ‘Father of the Skyscraper’ was pretty diminutive by today’s standards, towering all of ten floors to a height of 138ft but it was a trailblazing tower of its time.
After looking down on the cityscape from the SkyDeck on the first morning of our stay, we went on to spend much of our time over the ensuring days craning our necks skywards. A relaxing way to see more than 50 of Chicago’s most notable buildings, across a timespan of more than 125 years, is on The Architecture Foundation River Cruise. The 90-minute sailing gets off to an auspicious start close to the Gothic facade of the former newspaper offices of the Tribune Building and covers everything from Art Deco, Mid-20th Century Modern and Post Modern design styles to the ultra-contemporary glass-walled pavilion of the Apple Store.
Other sights include the Marina Building, where the two towers resemble giant sweetcorn cobs, the curvaceously contemporary Aqua hotel and residential block, and 333 West Wacker Drive, where the shimmering green structure flows in harmony with the river.
As we sailed beneath bascule bridges, which are opened by counterweights and another Chicago characteristic, we listened to an insightful live commentary about the city founded in 1837 that has reinvented itself on several occasions, most notably when a catastrophic fire in 1871 destroyed much of Chicago and left 100,000 people homeless. Other innovations include the ‘L’ (short for elevated) railway that rumbles over the streets. Having always thought the Windy City nickname related to the weather, I was also fascinated to hear that it’s actually a reference to verbose 19th century politicians who were derided for being ‘full of hot air’.
When it’s time for a break, Chicago has a burgeoning food and drink scene. There are 7,300 plus restaurants, 22 of which are Michelin starred, and upwards of 65 craft breweries as well as numerous bars at the forefront of the cocktail culture. But when in the city that invented the deep-dish pizza, then it has to be done. That night we went to Lou Malnati’s which is the oldest name in town. The namesake founder started working in the city’s first pizzeria in the 1940s and then founded his own. Malnati’s stands apart for its trademark buttery flaky crust and pizzas topped with jewel-bright vine-ripened plum tomatoes from California and Wisconsin cheese. The result is pretty epic in every sense of the word. The pizzas are huge, and certainly unlike anything I’ve ever seen or tasted in the UK. So just make sure you are very hungry when you order as most of us only managed two slices!
Next day we certainly needed a bit of exercise and another of the great things about Chicago is that it’s a very walkable city. A good place to start is the Magnificent Mile, dubbed the ‘Mag Mile’ by locals, which runs from the river down an upmarket stretch of Michigan Avenue where department stores such as Macy’s and Bloomingdales rub shoulders with more amazing architecture. One of the most photographed spots in town is Millennium Park, where you can get another perspective of the skyline reflected in the bright silver Cloud Gate sculpture created by British artist Anish Kapoor and affectionately known as ‘the bean’.
Come the evening Chicago has plenty to please the most dedicated night owls, including more than 200 theatres and virtually round the clock live music venues. We went to Kingston Mines, the city’s largest and oldest continuously operated blues club. It has a really friendly and inclusive vibe and two live stages that stay open until the early hours; up to 4:30am on Saturday night.
After a day’s sightseeing we were flagging well before midnight, but if you’ve got the energy you’re never going to run out of things to see, do and experience in a city where you can variously head for the dizzying heights one minute and head down the ‘mines’ later on.
Audley Travel offers a four-night Chicago break staying at the Omni Chicago Hotel, with a boat trip on the Chicago River and tickets to the observation deck at 360 Chicago, from £1,470 for travel in May 2020, including flights with Virgin Atlantic and Delta. For further details call +44 (0)1993 838 450 or visit www.audleytravel.com. For more information on Chicago and the Great Lakes region, please visit www.greatlakesusa.co.uk.
Known as the ‘River Cruise Queen’, Jeannine Williamson is an award-winning travel writer, cruise expert and our cruise correspondent, who has clocked up thousands of nautical miles.
Photographs courtesy of Choose Chicago
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