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Which Chicago neighbourhood is right for your client?
The Windy City, home to 77 neighbourhoods, is a buzzing urban hub with a whole lot of heart
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The Loop
Why go?
The beating heart of Chicago, The Loop is the city’s downtown core, with glossy mirrored skyscrapers jutting above historic landmarks, lively restaurants and swish rooftop bars.
It’s here that you’ll find the city’s famous Theatre District, the Chicago Riverwalk and Millennium Park – a sprawling green space that hosts regular concerts, with a buzz that extends well beyond the working week.
What to do
Start with a stroll through the park, home to The Bean, a shiny metal marvel by artist Anish Kapoor, where you can snap your morphed reflection in front of the city skyline.
If clients are here in summer, suggest staying on into the evening for one of the regular free outdoor concerts and film screenings put on as part of the Summer Music and Film Series.
Next to the park sits the Art Institute of Chicago, which was founded in 1879 and features one of the largest art collections in the US, including works by Picasso, Van Gogh, Warhol and Monet, alongside Chicagoan artists.
Then head to the Chicago Riverwalk, where restaurants and bars line a buzzing waterfront, or hop on a boat from Navy Pier to take in the skyline from a different perspective.
Great views can also be found from the Skydeck at Willis Tower (pictured), once the tallest building in the world. Go at night to see the city lights twinkle from a glass-floored platform, or try chic spot Cindy’s Rooftop for food and cocktails overlooking Millennium Park.
Little Village
Dulcelandia, Chicago. Image credit: Powell Photography, Inc.
Why go?
The ‘Mexico of the Midwest’, Little Village became the main entry point for Mexicans arriving in Chicago in the 1990s and, today, it’s one of the most vibrant and colourful spots in the city.
What to do
Start at the Little Village Arch, a terracotta archway built in 1990 to recognise the area’s Hispanic community. Amble to the Nuevo Leon Restaurant to see the huge, midnight-blue Day of the Dead mural, then stop at Dulcelandia (pictured) for an explosion of colour, with artisanal sweets stacked beneath bright piñatas.
Stop at the family-run Taqueria Los Comales for pork-filled tacos al pastor and milky drink horchata, then duck into Artesanias Elena to browse traditional Mexican crafts.
If you’re here on a summery Saturday, visit the Mercado de Colores, where streets teem with food vendors and live music, then end with a visit to Osito’s Tap, a speakeasy serving Latin-inspired cocktails.
Hyde Park
Griffin Museum of Science and Industry, Chicago. Image credit: Shutterstock/ezellhphotography
Why go?
Barack Obama’s former neighbourhood is something of a cultural gem on Chicago’s South Side. It’s the home of the University of Chicago – where the ex-president taught constitutional law for 12 years – as well as museums, parks and architectural treasures.
What to do
Come hungry for Valois Restaurant, a cash-only diner said to be one of Obama’s favourite breakfast spots; then walk it off at the Japanese-style Osaka Garden, dotted with waterfalls and cherry blossom trees.
Wander through to the elaborate Griffin Museum of Science and Industry and check out the University of Chicago campus, near the site of the soon-to-open Obama Presidential Center.
Then visit Unesco-listed Robie House, one of Frank Lloyd Wright’s famous feats of architectural genius, before hopping over to neighbouring Kenwood.
Gold Coast and Magnificent Mile
Chicago Water Tower. Image credit: Shutterstock/Nicholas J Klein
Why go?
One of the city’s glitziest neighbourhoods, the Gold Coast flanks Lake Michigan and is renowned for its opulent historic mansions, high-end boutiques and swanky restaurants.
What to do
Oak Street is at the heart of the neighbourhood, with its 19th-century architecture and upscale shops, while the nearby Museum of Contemporary Art Chicago is well worth a visit.
Take a guided tour of the geometric Charnley-Persky House, a National Historic Landmark designed by Frank Lloyd Wright and fellow architect Louis Sullivan.
The nearby Magnificent Mile is home to high-end shops, restaurants and architectural marvels such as the Chicago Water Tower.
Lincoln Park
Lincoln Park, Chicago. Image credit: tequilagraphics
Why go?
A short walk north of the Gold Coast, this picturesque park is home to trails, manicured gardens, a lily pond and zoo, with beaches right on the doorstep.
What to do
Take a stroll along the park’s waterfront boardwalk and cross the road to Montrose Beach, where alfresco restaurants, bars and volleyball courts line a stretch of powder-white sand.
Visitors looking to splash the cash will find several fine-dining restaurants in the locale, including three-Michelin-starred spot Alinea, and Esmé, which serves artfully designed tasting menus.
Afterwards, mosey over to Chicago’s Old Town to visit The Second City, an improv comedy club where Bill Murray made his name.
Wicker Park
Milwaukee Avenue, Chicago. Image credit: Shutterstock/John Gress Media Inc
Why go?
Once an industrial area, this is now home to live music venues, vintage boutiques, record stores and coffee shops, with a cool, hipster feel centred around the ‘Six Corners’.
What to do
Check out Milwaukee Avenue for boutiques, galleries and bookshops, or stretch the legs with a walk along The 606, an elevated walking trail on a former railway line framed with art installations.
The colourful outdoor tables at Ina Mae Tavern overflow on a sunny day, while live-music venue Subterranean, which hosts reggae and open-mic nights in an old-school industrial building, and street comedy typify Chicago’s friendly, diverse and liberal vibe – a true slice of this many-sided city.
Book it
Gold Medal sells a four-night room-only break at The LaSalle Chicago, Autograph Collection from £1,699 per person, based on two sharing a Superior King Room. The price includes United Airlines flights from Heathrow on April 20.
goldmedal.co.uk
America As You Like It offers four nights’ room-only at Palmer House, A Hilton Hotel, from £998 per person, based on two sharing next November. The price includes British Airways flights from Heathrow.
americaasyoulikeit.com
Where to stay in Chicago
Image credit: ANTHONY TAHLIER
The LaSalle Chicago, Autograph Collection: Set in the heart of downtown, this sleek boutique hotel is an excellent option for a luxury stay. Expect suave, contemporary rooms, and a bar and restaurant offering regular jazz performances.
There’s even a complimentary chauffeur service on weekends for trips within a two-mile radius. A night’s room-only in a Superior King Room starts at $329.
thelasallechicago.com
Image credit: Shutterstock/Nicholas J Klein
Palmer House, A Hilton Hotel: Located in a 150-year-old building near Millennium Park, Palmer House is something of an institution in Chicago – the brownie is said to have been invented there.
The lavish lobby has an all-day buzz and hosts regular live music. The hotel also offers a restaurant, several cafes, a speakeasy bar, spa, pool and fitness centre. A night’s room-only in a Standard Double Room starts at $186.
hilton.com
Things to do in Chicago
Image credit: Shutterstock/Joseph Hendrickson
Wrigley Field: Book a 90-minute tour to learn about the second-oldest baseball stadium in the US or coincide a visit with a Cubs game for a true taste of Americana.
mlb.com/cubs/ballpark
Image credit: Shutterstock/Ja Crispy
Chicago pizza tour: No visit to the city would be complete without a deep-dish pizza – and if you fancy sampling some of the best in the city with a local, book a trip with Chicago Pizza Tours. Foodies will pick up intriguing facts about the history of Chicago pizza and the city itself.
chicagopizzatours.com
Image credit: alicia fierro/aesthetiica 2021
AIRE Ancient Baths: Set in a historic building with exposed bricks, this spa is as calming as it gets. Expect serene music and candles as you enjoy a series of baths and steam rooms inspired by ancient cleansing rituals, including a floating pool and salt scrub.
beaire.com
Lead image credit: Ranvestel Photographic
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