The curvilinear Cloud Gate, the amorphous Anish Kapoor sculpture sited near the entrance of Chicago’s Millennium Park, is not just a work of blazing originality. Simultaneously playful and stylish, user-friendly and abstract, the 110-tonne sculpture, modelled on a drop of liquid mercury, has become a symbol of the new Chicago, a city that once followed trends and now dictates them.
It’s an apt visual metaphor for the Windy City, a place that has always struggled with its identity. Now, more than five years after Kapoor’s sculpture held its triumphant unveiling, Chicago is undergoing a revival on many fronts, architecture, cuisine and the arts among them.
Locals point to Millennium Park, which opened in 2004, as a definite turning point. Now a cultural anchor for the city, this marvellous park features the Jay Pritzker Pavilion designed by Frank Gehry, interactive LED fountains by Jaume Plensa, and Kapoor’s wonderfully appealing sculpture. The area, which was transformed from an industrial wasteland of abandoned railroad tracks and parking lots, felt like a lakeside blight on the city for most of the 20th century. A visit here is a sensory experience – children play in the interactive fountain, families picnic on the large expanses of grass, and others come to simply admire the city’s unbeatable collection of architectural marvels, running the aesthetic gamut from the neo-Gothic Tribune Tower to Mies Van der Rohe’s slick International Style skyscrapers.
Chicago has always balanced the classical and the modern with prowess. A short stroll from Cloud Gate stands another marvel of design, the Art Institute of Chicago, a magnificent 1893 Beaux Arts building, which recently unveiled its US$294 million addition. The striking and graceful work sprang from the imagination of Renzo Piano, who was charged with creating a modern wing for the institution’s vast 260,000-strong collection of art treasures. Now the second largest museum in the United States, it’s a must-visit destination.
For the architecturally inclined, Chicago offers numerous pilgrimages: a ride to the top of the Hancock Tower, once the highest skyscraper on Earth; a visit to Oak Park, the childhood home of Frank Lloyd Wright and site of many of his seminal prairie-style homes; and a 90-minute architectural cruise along the river, one of the best vantage points from which to appreciate the city’s collection of architectural wonders.
Architecture aside, historically Chicago has never been thought of as one of the world’s most stylish cities, but that too is changing. The Obamas, considered the most fashionable first couple to emerge in some time, have lent their hometown a certain refracted glow in addition to what some businesses have called the “Obama bump”. Unlike former president Bush, who was a self-confessed homebody, the Obamas revelled in their city: they marked special occasions at Spiaggia, the lavish Italian restaurant; enjoyed margaritas at Rick Bayless’ renowned Mexican restaurants, the adjacent Topolobampo and Frontera Grill; and made family outings to Promontory Point Park, a green expanse on the shores of Lake Chicago, home to biking and hiking trails with superb views of the city’s famous skyline.
Michelle Obama, known for her astute fashion choices, also developed her highly attuned sense of style in the city. Chicago is a shopper’s Shangri-La; the Magnificent Mile – a grand thoroughfare in downtown Chicago, which was laid out in the 1909 Plan of Chicago – is the quickest way to get a retail fix. Lined with classic American brands such as Bloomingdales, Abercrombie & Fitch, Ralph Lauren and Niketown, the Midwestern shopping mecca claims more than 278,709sqm of retail space. Oprah Winfrey and other Chicago celebrities favour the Gold Coast, a blue-chip area, which counts the city’s rich and famous as its polished denizens. Designer Tory Burch, home furnishings guru Jonathan Adler and Barney’s New York have all opened spaces in the neighbourhood. Ikram on Rush Street, owned by Ikram Goldman, the unofficial clothier of Michelle Obama, is a standout – the place overflows with hand-selected women’s clothing by the likes of Alexander McQueen and Azzedine Alaia.
And then there’s the food. Over time, the one-time meatpacking capital has experienced a change of appetite. Tasting a deep-dish pizza or sampling Chicago-style hotdogs remain tourism rites, but these days Chicago ranks as an epicurean capital par excellence. The Windy City is rife with innovative young chefs moving in all sorts of interesting directions. Grant Achatz, who commands a cult following in the food world, is the owner and chef at Alinea, known for its blend of exquisite food and molecular technique (and a hefty waiting list). Other chefs, including Schwa’s Michael Carlson, have followed in his footsteps, crafting unexpected idiosyncratic dining spaces that feel simultaneously comfortable and avant-garde.
It’s those paradoxes that actually serve to describe the city best. Chicago is a place that inspires but rarely intimidates. It awes with its scale, but remains thoroughly liveable.
When Daniel Burnham, the city’s master planner and architect once declared, “make no little plans”, he ushered in the City Beautiful movement and may well have prescribed the city’s can-do attitude. Almost a century after Burnham’s death the refrain holds true – here in the Midwest is a city with endless all-American appeal that continues to move purposefully towards the future.
Chicago Hotels
From ultra-luxury towers to boutique boltholes overflowing with personality, Chicago’s hotels are as diverse as the city itself and offer something for everyone.
The Peninsula Chicago
Regularly recognised as the city’s luxury hotel nonpareil, this luxury property boasts the same attention to detail as its Asian predecessors. Guestrooms feature the group’s award-winning technology (televisions in the bath are a nice touch) and many have jaw-dropping views.
108 East Superior Street. tel +1 312 337 2888. http://chicago.peninsula.com
The James Chicago
Featuring custom artwork, slick Scandinavian furniture and an ever-popular bar and restaurant, this 297-room hotel is a favourite of visiting celebrities. But don’t expect attitude: The James prides itself on its friendly staff, who known the town well and are always happy to share advice.
55 East Ontario. tel +1 312 337 1000. www.jameshotels.com
Talbott Hotel
For those looking for a modestly priced but well-located hotel, look no further. With its smaller scale and intimate lobby, the Talbott is steps away from the Gold Coast’s fine restaurants, big-ticket stores and bars.
20 East Delaware Place. tel +1 312 944 4970. www.talbotthotel.com
Windy City Neighbourhoods
Less a city than a pastiche of vibrant polyglot neighbourhoods, Chicago will astound you with its diversity. Don’t visit the city without delving into these cool corners.
Wicker Park
Undeniably cool, this vibrant enclave has it all – contemporary art, cool boutiques, excellent restaurants and atmospheric bars.
SHOP: RR#1
Explore the city’s current penchant for the past at this quirky-cool boutique. Set in a 1930s apothecary, the store overflows with locally made candles and products, vintage glassware and jewellery.
814 North Ashland Ave; tel +1 312 421 9079; www.rr1chicago.com
EAT: Big Star
Join the crowds and beat a path for whiskey and tacos at this raffishly hip eatery, a casual counterpoint to James Beard award-winning chef Paul Kahan’s other acclaimed dining spaces.
1531 North Damen Ave; tel +1 773 235 4039; www.bigstarchicago.com
DRINK: Map Room
This self-described “Traveller’s Tavern” is arguably the best place in the city for beer lovers. Shelves hold travel ephemera, atlases and guides, and the drinks list is equally peripatetic, featuring excellent brews from all corners of the globe.
1949 North Hoyne Ave; tel +1 773 252 7636; www.maproom.com
Logan Square
Two decades ago, this historically significant area was riddled with crime and social problems. Flash forward to today, and it’s become a haven of innovative restaurants, unpretentious stores and restored tree-lined boulevards.
SHOP: Margie’s Candies
An old-fashioned ice-cream shop with jukeboxes still on the tables, this place dispenses ice-cream sundaes and a great selection of handmade chocolates, fudge and candy. It’s a time warp.
1960 North Western Ave; tel +1 773 384 1035
EAT: Longman & Eagle
With its six guestrooms upstairs, this rough-hewn bar and restaurant exudes laid-back residential cool. Regulars swear by the crab eggs Benedict and the pork belly BLT.
2657 North Kedzie Ave; tel +1 773 276 7110, http://longmanandeagle.com
DRINK: The Whistler
Recently ranked by GQ magazine as one of the 25 best cocktail bars in America, this music venue has evolved to become the go-to place for classical mixology.
2421 North Milwaukee Ave; tel +1 773 227 3530
River North
Until the 1970s this newly popular area was an industrial zone. With the Chicago River as its boundary, the neighbourhood has spectacular views, converted loft apartment buildings and plenty of local hangouts. The River North neighbourhood is also the site of the city’s premier gallery district, made up of old redbrick warehouses transformed into capacious exhibition spaces.
SHOP: Abraham Lincoln Book Shop
Here, amid galleries and design studios, is a one-of-a-kind store specialising in historical documents and literature. Originally opened in 1938, it feels a little like a time machine.
357 West Chicago Ave; tel +1 312 944 3085; www.alincolnbookshop.com
EAT: Lou Malnati’s Pizzeria
Build up an appetite if you’re going to try Chicago’s famous deep-dish pizza at this venerable institution known for its thick, bready crusts and rich sauce.
439 North Wells St; tel +1 312 828 9800; www.loumalnatis.com
DRINK: Frontera Grill
Though it’s technically a restaurant, Rick Bayless’ iconic regional Mexican joint mixes a fine margarita, a Chicago essential.
445 North Clark St; tel +1 312 661 1434; www.rickbayless.com
Locals point to Millennium Park, which opened in 2004, as a definite turning point. Now a cultural anchor for the city, this marvellous park features the Jay Pritzker Pavilion designed by Frank Gehry, interactive LED fountains by Jaume Plensa, and Kapoor’s wonderfully appealing sculpture. The area, which was transformed from an industrial wasteland of abandoned railroad tracks and parking lots, felt like a lakeside blight on the city for most of the 20th century. A visit here is a sensory experience – children play in the interactive fountain, families picnic on the large expanses of grass, and others come to simply admire the city’s unbeatable collection of architectural marvels, running the aesthetic gamut from the neo-Gothic Tribune Tower to Mies Van der Rohe’s slick International Style skyscrapers.
Chicago has always balanced the classical and the modern with prowess. A short stroll from Cloud Gate stands another marvel of design, the Art Institute of Chicago, a magnificent 1893 Beaux Arts building, which recently unveiled its US$294 million addition. The striking and graceful work sprang from the imagination of Renzo Piano, who was charged with creating a modern wing for the institution’s vast 260,000-strong collection of art treasures. Now the second largest museum in the United States, it’s a must-visit destination.
For the architecturally inclined, Chicago offers numerous pilgrimages: a ride to the top of the Hancock Tower, once the highest skyscraper on Earth; a visit to Oak Park, the childhood home of Frank Lloyd Wright and site of many of his seminal prairie-style homes; and a 90-minute architectural cruise along the river, one of the best vantage points from which to appreciate the city’s collection of architectural wonders.
Architecture aside, historically Chicago has never been thought of as one of the world’s most stylish cities, but that too is changing. The Obamas, considered the most fashionable first couple to emerge in some time, have lent their hometown a certain refracted glow in addition to what some businesses have called the “Obama bump”. Unlike former president Bush, who was a self-confessed homebody, the Obamas revelled in their city: they marked special occasions at Spiaggia, the lavish Italian restaurant; enjoyed margaritas at Rick Bayless’ renowned Mexican restaurants, the adjacent Topolobampo and Frontera Grill; and made family outings to Promontory Point Park, a green expanse on the shores of Lake Chicago, home to biking and hiking trails with superb views of the city’s famous skyline.
Michelle Obama, known for her astute fashion choices, also developed her highly attuned sense of style in the city. Chicago is a shopper’s Shangri-La; the Magnificent Mile – a grand thoroughfare in downtown Chicago, which was laid out in the 1909 Plan of Chicago – is the quickest way to get a retail fix. Lined with classic American brands such as Bloomingdales, Abercrombie & Fitch, Ralph Lauren and Niketown, the Midwestern shopping mecca claims more than 278,709sqm of retail space. Oprah Winfrey and other Chicago celebrities favour the Gold Coast, a blue-chip area, which counts the city’s rich and famous as its polished denizens. Designer Tory Burch, home furnishings guru Jonathan Adler and Barney’s New York have all opened spaces in the neighbourhood. Ikram on Rush Street, owned by Ikram Goldman, the unofficial clothier of Michelle Obama, is a standout – the place overflows with hand-selected women’s clothing by the likes of Alexander McQueen and Azzedine Alaia.
And then there’s the food. Over time, the one-time meatpacking capital has experienced a change of appetite. Tasting a deep-dish pizza or sampling Chicago-style hotdogs remain tourism rites, but these days Chicago ranks as an epicurean capital par excellence. The Windy City is rife with innovative young chefs moving in all sorts of interesting directions. Grant Achatz, who commands a cult following in the food world, is the owner and chef at Alinea, known for its blend of exquisite food and molecular technique (and a hefty waiting list). Other chefs, including Schwa’s Michael Carlson, have followed in his footsteps, crafting unexpected idiosyncratic dining spaces that feel simultaneously comfortable and avant-garde.
It’s those paradoxes that actually serve to describe the city best. Chicago is a place that inspires but rarely intimidates. It awes with its scale, but remains thoroughly liveable.
When Daniel Burnham, the city’s master planner and architect once declared, “make no little plans”, he ushered in the City Beautiful movement and may well have prescribed the city’s can-do attitude. Almost a century after Burnham’s death the refrain holds true – here in the Midwest is a city with endless all-American appeal that continues to move purposefully towards the future.
Chicago Hotels
From ultra-luxury towers to boutique boltholes overflowing with personality, Chicago’s hotels are as diverse as the city itself and offer something for everyone.
The Peninsula Chicago
Regularly recognised as the city’s luxury hotel nonpareil, this luxury property boasts the same attention to detail as its Asian predecessors. Guestrooms feature the group’s award-winning technology (televisions in the bath are a nice touch) and many have jaw-dropping views.
108 East Superior Street. tel +1 312 337 2888. http://chicago.peninsula.com
The James Chicago
Featuring custom artwork, slick Scandinavian furniture and an ever-popular bar and restaurant, this 297-room hotel is a favourite of visiting celebrities. But don’t expect attitude: The James prides itself on its friendly staff, who known the town well and are always happy to share advice.
55 East Ontario. tel +1 312 337 1000. www.jameshotels.com
Talbott Hotel
For those looking for a modestly priced but well-located hotel, look no further. With its smaller scale and intimate lobby, the Talbott is steps away from the Gold Coast’s fine restaurants, big-ticket stores and bars.
20 East Delaware Place. tel +1 312 944 4970. www.talbotthotel.com
Windy City Neighbourhoods
Less a city than a pastiche of vibrant polyglot neighbourhoods, Chicago will astound you with its diversity. Don’t visit the city without delving into these cool corners.
Wicker Park
Undeniably cool, this vibrant enclave has it all – contemporary art, cool boutiques, excellent restaurants and atmospheric bars.
SHOP: RR#1
Explore the city’s current penchant for the past at this quirky-cool boutique. Set in a 1930s apothecary, the store overflows with locally made candles and products, vintage glassware and jewellery.
814 North Ashland Ave; tel +1 312 421 9079; www.rr1chicago.com
EAT: Big Star
Join the crowds and beat a path for whiskey and tacos at this raffishly hip eatery, a casual counterpoint to James Beard award-winning chef Paul Kahan’s other acclaimed dining spaces.
1531 North Damen Ave; tel +1 773 235 4039; www.bigstarchicago.com
DRINK: Map Room
This self-described “Traveller’s Tavern” is arguably the best place in the city for beer lovers. Shelves hold travel ephemera, atlases and guides, and the drinks list is equally peripatetic, featuring excellent brews from all corners of the globe.
1949 North Hoyne Ave; tel +1 773 252 7636; www.maproom.com
Logan Square
Two decades ago, this historically significant area was riddled with crime and social problems. Flash forward to today, and it’s become a haven of innovative restaurants, unpretentious stores and restored tree-lined boulevards.
SHOP: Margie’s Candies
An old-fashioned ice-cream shop with jukeboxes still on the tables, this place dispenses ice-cream sundaes and a great selection of handmade chocolates, fudge and candy. It’s a time warp.
1960 North Western Ave; tel +1 773 384 1035
EAT: Longman & Eagle
With its six guestrooms upstairs, this rough-hewn bar and restaurant exudes laid-back residential cool. Regulars swear by the crab eggs Benedict and the pork belly BLT.
2657 North Kedzie Ave; tel +1 773 276 7110, http://longmanandeagle.com
DRINK: The Whistler
Recently ranked by GQ magazine as one of the 25 best cocktail bars in America, this music venue has evolved to become the go-to place for classical mixology.
2421 North Milwaukee Ave; tel +1 773 227 3530
River North
Until the 1970s this newly popular area was an industrial zone. With the Chicago River as its boundary, the neighbourhood has spectacular views, converted loft apartment buildings and plenty of local hangouts. The River North neighbourhood is also the site of the city’s premier gallery district, made up of old redbrick warehouses transformed into capacious exhibition spaces.
SHOP: Abraham Lincoln Book Shop
Here, amid galleries and design studios, is a one-of-a-kind store specialising in historical documents and literature. Originally opened in 1938, it feels a little like a time machine.
357 West Chicago Ave; tel +1 312 944 3085; www.alincolnbookshop.com
EAT: Lou Malnati’s Pizzeria
Build up an appetite if you’re going to try Chicago’s famous deep-dish pizza at this venerable institution known for its thick, bready crusts and rich sauce.
439 North Wells St; tel +1 312 828 9800; www.loumalnatis.com
DRINK: Frontera Grill
Though it’s technically a restaurant, Rick Bayless’ iconic regional Mexican joint mixes a fine margarita, a Chicago essential.
445 North Clark St; tel +1 312 661 1434; www.rickbayless.com 
