Chicago travel: Culture club thriving in the art of the city

Chicago travel: Culture club thriving in the art of the city

WITH attractions galore and easy navigation Nicola Bartlett reveals why your next trip across the pond should be to the Windy City

With its defining architecture, world-class museums and thriving arts scene, Chicago is America’s favourite city break. Set on the banks of Lake Michigan, Illinois, it has all the buzz of New York as well as the sass of San Francisco but here there’s space to breathe.


To get a sense of the city, whizz 103 floors up to the top of the famous Willis Tower and peek down through the glass floor – if you dare.

Gaze out on to the grid-pattern streets which make up the 77 colourful neighbourhoods. Each has its own character and identity, reflecting the rich cultural heritage of the city. This includes Pilsen, an artful, predominantly Latino area and home to the National Museum of Mexican Art; the creative epicentre of Wicker Park with its quirky cafes and vintage shops and the affluent Gold Coast area with its designer stores, chic hotels and mansions.

Chicago is also a beautiful city to explore on foot – Millennium Park is popular for its skyline views and truly amazing pieces of public art. Anish Kapoor’s silver, ultra-reflective Cloud Gate, known as “the bean”, makes for great photos, while Jaume Plensa’s Crown Fountain – two glass brick walls showing videos of faces that occasionally spit out jets of water – will make you chuckle.

If you’re visiting in the summer months, vast Lake Michigan adopts a seaside-vibe when the waterfront transforms into a series of beaches.

To get around, hop on the Metra or CTA trains, grab an Uber or Lyft.

Alternatively, borrow a bike from one of the many stands dotted through the city via the Divvy app.


Take a Greeter Tour, a free service run by the Chicago tourist office that matches visitors with enthusiastic, city-knowledgeable residents.

Ours showed us where Michelle and Barack Obama had their first kiss (there is a plaque) outside a former Baskin-Robbins icecream shop at Dorchester Avenue and 53rd Street in the Hyde Park neighbourhood. We also stopped off to see where the former US president used to get his hair cut. At the Hyde Park Hair Salon an “Obama” costs $30.

Then admire prairie-style homes – The Robie House and The Heller House – designed by acclaimed architect Frank Lloyd Wright.

To fully appreciate Chicago’s stunning skyline, hop on Shoreline Sightseeing’s 75-minute Architecture Tour by boat. Sailing down three branches of the Chicago River, it passes more than 40 of its most famous landmarks including the neo-Gothic Tribune Tower and the Marina Towers, known by locals as the “corn cobs” which featured in the 1986 film, Ferris Bueller’s Day Off.

Want to see the city’s dark side? Escape into Chicago’s underworld on a crime tour to discover where some of the world’s most notorious villains, including Al Capone, John Dillinger and HymieWeiss, bamboozled their way through the streets.

Notable bone-chilling sights include the place of Chicago’s notorious StValentine’s Day massacre.


The Promontory, in Hyde Park, is a multi-level restaurant and live music venue, great for laid-back brunches and suppers. Try the house salad with hazelnut dukkah, pickled butternut squash and grilled halloumi. Diners can step upstairs for jazz, hip-hop and soul music or chill out on the decking around the fit pit, to soak up the views over Promontory Point which stretches out into Lake Michigan.

Sleek dining spot Mesler, at the Sophy Hotel, also in Hyde Park, serves creative dishes and cocktails in a restaurant filled with colourful modern artworks from Chicago artists and a library of books.


The speakeasy was a key feature of the Prohibition period and you can tap into that illicit vibe at the Chicago Magic Lounge in Andersonville which has two false entrances. Sneak in through the laundrette which opens up into a library, bar and theatre. The master-illusionists astound audiences with their shows here, plus magicians perform card tricks at close quarters, wowing guests sitting at tables.

Chicago is also a famous music city and at Buddy Guy’s Legends, you might get to hear the man himself, an eight-time, Grammy Award-winning blues legend, as well as up-and-coming acts, seven nights a week.

Kingston Mines, founded in 1968, is the largest and oldest continuously operating blues club in Chicago. It has two live stages and is open every night until 5am.

Boystown, the first officially recognised gay village in the US, is the affectionate term for the eclectic Lakeview East neighbourhood. Brunch at the Kit Kat Lounge & Supper Club comes with a side order of drag queens and bottomless cocktails.


Home to around 200 theatres, Chicago is a hotbed for exciting new work and hundreds of world premieres every year.