If you’re unfamiliar with Chicago, odds are your impressions of this great metropolis won’t include fine dining, rock climbing and swathes of open green spaces. But like so many things about the Windy City, the reality may surprise you.
Even its nickname is misleading – referring not to the chilly gusts coming off Lake Michigan, say locals, but rather to Chicago’s famously long-winded politicians (with the exception of the city’s adopted son, former resident Barack Obama, of course).
So just why is Chicago such a breath of fresh air for visitors?
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What to see
If there’s one thing you probably are familiar with, it’s that skyline. Featuring four of the eight tallest buildings in the US, Chicago is home to some of the finest architecture on the planet. It’s awe-inspiring, and all the more so considering that most of the city has been built within the last 140-odd years, following a devastating fire in 1871.
For the best viewing experience, step out into one of the glass boxes at Skydeck Chicago, suspended more than 1,300ft in the sky at the top of the Willis Tower – previously the Sears Tower – where you can enjoy a vista over the city, Lake Michigan and, on a clear day, beyond to the four surrounding states. Like walking on air above a patchwork of shrunken skyscrapers and ant-size cars, it’s an almost out-of-body sensation. Just don’t look down. Thrill seekers may also enjoy 360 Chicago, on the 94th floor of the John Hancock Center, where visitors are tilted out over the edge of the building at a 30-degree angle.
Of course, no trip to Chicago is complete without a sightseeing cruise. Charter a private yacht to set sail in style on the vast – it accounts for 20% of the world’s fresh surface water – Lake Michigan. Or for a magical two-in-one experience, you can’t beat a sunset cruise along the three branches of the Chicago River on Chicago’s Original Architecture Tour, winding through the heart of the city while an impressively knowledgeable guide tells the stories behind landmarks such as the neo-Gothic Tribune Tower and the marble-coated Aon Centre. Dotted between these towering structures you may also spot a few of the hundreds of artworks on display citywide to celebrate the 2017 Year of Public Art.
And then there’s Chicago’s natural works of art...
Maggie Daley Park play garden
What to do
Back in the 1830s, Chicago, then little more than a swampy outpost, optimistically adopted the motto “urbs in orto”, or city in a garden. Today, it’s clear that optimism bore fruit, with a series of generous parks dotted across its 77 neighbourhoods.
One of the newest is Maggie Daley Park, opened in 2015, which covers 28 acres along the lakefront in the downtown district and acts as a giant green roof over an underground garage. Carefully constructed curves, hills and valleys block out the wind and traffic noise to create an oasis of calm dedicated to recreation and relaxation. You really do forget you’re in the heart of a bustling city, until you look up at the surrounding high-rises. Attractions include a three-acre play garden that conjures up the spirit of Alice in Wonderland, tennis courts, mini golf and, snaking around the park, the quarter-mile-long, 20ft-wide Ice Skating Ribbon (open November to March). And at the centre of this skating route sits one of the world’s largest outdoor climbing walls, which reaches up to 45ft and has space for 100 climbers.
For a more sedentary experience, stroll across the bridge connecting Maggie Daley Park to Millennium Park – home to a wealth of outdoor artworks, including the mesmerising Cloud Gate sculpture, also known as The Bean, by Indian-born British artist Sir Anish Kapoor. This park is also the site of the brilliantly sci-fi-looking Jay Pritzker Pavilion, with a bandstand of brushed steel ribbons framing the huge outdoor stage, and seating for up to 11,000 people. The pavilion hosts a summer schedule of free music and movies, and the Chicago Symphony Orchestra practise there every lunchtime, too, making it a perfect picnic spot.
The Cloud Gate sculpture, aka The Bean
If you’re happy to park your dignity at the door, there are few more fun ways to see the city than on an Absolutely Chicago Segway Tour. Chatty guides provide interesting insights and insider gossip during an eight-mile glide (once you’ve mastered your balance) along the lakeside from Millennium Park to the Museum Campus, site of four of the city's most notable attractions: the Adler Planetarium; Shedd Aquarium; The Field Museum of Natural History; and Soldier Field American football stadium, home of the NFL’s Chicago Bears. For Godfather fans, there’s also a gangsters-themed segway tour, taking in the favourite old haunts of Al Capone and his crew.
Further afield, but well worth a visit, the 606 park and trail system connects four North Westside neighbourhoods via a 2.7-mile-long elevated route built atop a 100-year-old concrete railway embankment, with a series of distinct garden “rooms” along the way. The route - which gets its name from the first three numbers in the zip codes that Chicagoans share - goes through hipster areas including Bucktown and Wicker Park, and with plenty of exit ramps, it’s easy to hop off for a spot of shopping and food.
Tortoise Supper Club
Where to eat
Chicagoans take their food very seriously, and for good reason – as you’ll discover if you try a Chicago-style hot dog, topped with mustard, gherkin relish, tomatoes, jalapenos and a sprinkling of celery salt. But while the city does a fine line in street food, it’s the range of restaurants on offer that really whets the appetite.
The food that put Chicago on the culinary map is, of course, deep-dish pizza. Even if you’re not usually a deep-dish fan, take it from a convert, the Chicago-style version is nothing like the wodges of stodge lurking in supermarket freezers. Gino’s East North River, housed in a former cable-car powerhouse, has won a loyal local following with its legendary pizzas, or “pies”: a wide bowl of medium-thick golden pastry filled with a mound of mozzarella that, crucially, sits beneath a thick layer of chunky tomato sauce (to prevent the cheese from burning) and other assorted toppings. It’s as delicious as it is button-bustingly filling. (A word of advice: leave your skinny jeans at home.)
For the finest fried chicken and cheese curd fritters in the city, head to Parson’s Chicken and Fish, a low-key diner with an ultra-relaxed vibe in the tree-lined Logan Square neighbourhood. The American-style baked beans, made with molasses, brown sugar and vinegar, are also world class (sorry, Mr Heinz, but no contest), and the boozy slushies are not to be missed either.
It would be a shame, too, to miss out on Chicago’s many fine-dining experiences. The downtown Tortoise Supper Club serves upmarket steaks, chops and seafood against a backdrop of live jazz, complete with grand piano. It’s like a modern-day speakeasy, but with better food and fewer cigar-chomping gangsters.
For pre- or post-dinner cocktails, check out Cindy’s, a 13th-floor rooftop bar with fantastic views over Lake Michigan (and equally steep prices). Or beer lovers may want to try the city’s many craft breweries, such as the atmospheric Alulu Brewpub, in the aptly named Pilsen district. Wherever you go, for a truly memorable evening, end the night at one of Chicago’s piano bars, such as The Redhead, where obliging pianists accept requests for singalongs to tunes by everyone from Frank Sinatra to Cyndi Lauper. Cheesy, yes; fun, absolutely.
Where to stay
Ideally located just two-and-a-half blocks from shoppers’ paradise the Magnificent Mile, in the River North district, the Acme Hotel Company is a boutique hotel that’s simultaneously hip, bohemian and retro, but also friendly and unintimidating. Think Hoxton rather than Hyde Park.
As well as huge comfy beds, the rooms feature outsize TVs, free Wi-Fi, splattered-handprint wall art and red light-up lips on the bathroom mirror (a sort of nightlight for grown-ups). Many of the suites are equipped with electric guitars, in case you want to rock out, and all rooms have an Amazon Alexa, which you can use, should you wish, to order coffee - you can have a thermos-full of freshly brewed joe delivered, for free, to your door each morning.
That caffeine jolt comes courtesy of the Acme’s in-house West Town Bakery, a popular breakfast destination for guests and locals alike. Across the hallway is the hotel’s spacious old-style cocktail lounge, the Berkshire Room, while below, in the basement, is a hot tub, sauna and a gym, to work off the bakery’s all-too-tempting cake balls. And in keeping with the hotel’s high-tech credentials, guests are offered free loans of Apple watches and – this is genius – mobile hotspots, meaning you can take Wi-Fi with you when you explore the streets. Like Chicago itself, it’s these unexpected touches that make the Acme a must-try destination.
Prices start from $89 (£67) per night for a standard room, and $169 (£127) for a suite.
How to get there
Iceland’s budget airline Wow Air recently launched a five-times-weekly flight from London Gatwick to Chicago, via Reykjavik, from £140 one way. Wow Air also has four weekly flights from Edinburgh to Chicago via Iceland.
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