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The great Midwestern city of Chicago owes its imposing skyline to two things: the Great Chicago Fire in 1871 and the Chicago Columbian Exposition in 1893. The former razed much of the city, sparking a new vernacular of fireproof building (and giving rise to the world’s first skyscraper in 1885), while the latter was an architectural laboratory that spurred on the city’s progressive planning.
Frank Lloyd Wright once declared: ‘Eventually, I think Chicago will be the most beautiful great city left in the world.’ Indeed, eight of his buildings were collectively awarded UNESCO World Heritage status, including the Frederick C Robie house (1908-1910), located in Obama’s old hood of Hyde Park, and Unity Temple (1905-1908), near the architect’s first home and studio in the Oak Park suburb. Areas well worth a tour – on foot, bike or even Segway.
Where to stay
The Chicago Athletic Association hotel, with interiors designed by Roman and Williams, is a design aficionado’s delight with its mix of Venetian gothic and sports-themed details – an ode to its 1890s athletic club origins. Its rooftop bar Cindy’s has amazing city views of Millennium Park opposite, while fine dining is provided at the Cherry Circle Room and cocktails in the speakeasy Milk Room.
Or else head to the hip neighbourhoods of Wicker Park or Lincoln Park, where you’ll find sleek mid-century-modern hotel The Robey, with rooftop pool and amazing city views, and the contemporary vintage vibe of Hotel Lincoln, respectively. For good value and great style close to the Loop’s shops, museums and restaurants, stay at Freehand Chicago.
Eating & Drinking
Chicago is big on craft breweries, coffeehouses and specialities such as deep-dish pizza, Italian beef sandwiches and fried chicken (try Parson’s Chicken & Fish). For brunch favourites, salads and lobster rolls, eat under the dazzling chandelier hanging in the sky-lit garden courtyard of the elegant but relaxed 3 Arts Club Café inside Restoration Hardware’s six-floor furniture and homeware emporium.
The Purple Pig is great for sharing platters – alongside the pork specialties, there are delicious vegetable, poultry and seafood dishes, great wines and hearty desserts. The West Loop is the spot for some of the city’s hottest restaurants (all oozing with Chicago’s distinctive industrial-meets-rustic chic): local chef Stephanie Izard’s Girl & the Goat, Duck Duck Goat and Little Goat Diner, emphasising family-style dishes (yes, there’s goat in the mix) with a fresh Asian twist – she’s also behind nearby The Hoxton Chicago’s rooftop Cabra Cevicheria.
Au Cheval for upmarket diner classics; Avec, where the Med meets the Midwest; and the dual-concept Smyth + The Loyalist, with a farm-to-table tasting menu restaurant on the first floor and a cool lounge bar below. And for afters, try a butterscotch or boozy hot chocolate – served with a homemade marshmallow – with a donut at Mindy’s Hot Chocolate Chicago in Wicker Park.
Art & Culture
The Chicago Architecture Centre is a must for insight into how Chicago was born and built, while the Art Institute of Chicago boasts one of the world’s most impressive collections.
In Millennium Park, find Frank Gehry’s Jay Pritzker Pavilion and Anish Kapoor’s gleaming Cloud Gate sculpture, aka ‘The Bean’ (top). The city itself is a virtual art gallery – don’t miss Alexander Calder’s Flamingo outside Mies van der Rohe’s Chicago Federal Centre in the Loop, Picasso’s untitled 50ft Corten-steel sculpture in Daley Plaza opposite Monument with Standing Beast by Jean Dubuffet, and Joan Miró’s mixed-media Chicago at Brunswick Plaza.
For vibrant street art, head to areas like Rogers Park, Logan Square and Pilsen.
To find the best independent shopping, you need to travel around the city. Volume Gallery showcases rising American designers in sculpture, textiles, lighting, ceramics and furniture; there’s natural, affordable skincare (including a popular mask bar) at Scratch Goods; chic notebooks and notelets at Greer and an ever-changing array of fashion, art and interior pieces – showcased in a quirky, art-strewn warehouse space – at Rider for Life.
For contemporary and vintage furniture, head to Jayson Home; try stylish concept store Space 519 for global fashion, jewellery, books, beauty and an all-day café; find boho-cool homeware by local makers at Humboldt House; all things beauty and bath at the old-school Merz Apothecary and pop into the RSVP Gallery for cool urban fashion and accessories.
Escape the city
From Chicago, head an hour west to Farnsworth House, Mies van der Rohe’s iconic 1951 cantilevered floating glass box on the banks of the Fox River in Plano, and eat at nearby sustainable gastro pub Hardware, which has its own brewery, farm and 450-plus whiskeys to choose from.
Alternatively, travel northwest to Rockford for Frank Lloyd Wright’s 1950s Usonian-hemicycle Laurent House (one of the architect’s favourite, and last, projects, or visit Evanston, a half-hour train ride north of the city, for The Bahá’í House of Worship, an extraordinary decoratively carved concrete temple finished in 1953, designed by Canadian architect Louis Bourgeois.
And if you’ve got time, make sure to ogle at the impressive modern stained glass in the Alice Millar Chapel.
Meet the Insiders: Studio Gang
Founded by award-winning architect Jeanne Gang in 1997, Studio Gang is renowned for Nature Boardwalk at Lincoln Park Zoo; 82-storey Aqua Tower, distinctive for its undulating façade; and the 101-storey Vista Residences tower, which is set to be the world’s tallest building designed by a woman. Here, Gang and her team share their favourite Chicago hotspots. studiogang.com
■ Dark Matter Coffee: the best coffee in town – take a pack of Unicorn Blood Espresso Blend to go.
■ Elizabeth: great restaurant for farm-to-table fare.
■ Garfield Park Conservatory: an extensive botanical conservatory set within a 184-acre urban park.
■ Graham Foundation: see exhibitions exploring the role of architecture across society.
■ Chicago Cultural Centre: free exhibitions, events and the world’s largest Tiffany stained-glass dome.