Chicago has levelled up its culinary game in recent years – but deep-dish pizza, the city’s hometown specialty, remains a favourite. Visit institutions like Pizzeria Uno, said to be the birthplace of the iconic thick crust in 1943, or head to the famous Rosati’s, which has specialised in pizza since 1964. Can’t choose? Hop on the Chicago Pizza Tour to try a slice of everything.

Among the many places to visit in Chicago are its museums, which span the groundbreaking and the bizarre. Get your art fix at the Art Institute of Chicago (immortalised in Ferris Bueller’s Day Off) and the Museum of Contemporary Art, with impressive collections spanning centuries and the globe. For something a little more offbeat, then trace the occasionally gruesome history of medicine at the International Museum of Surgical Science.

The Hubbard Street Murals have been brightening up 11 blocks of a railroad embankment since the early 1970s. While few of the original murals remain, a government-sponsored cultural initiative has seen the revival of the area. And along Wabash Avenue you’ll find Wabash Arts Corridor, one of the largest public art programmes in the country, home to murals, large-scale projectsion, installations – and even performances.

One of the best ways to take in this gleaming metropolis is from the water. The Chicago Architecture Center offers a 90-minute river cruise that tells the stories of 50 buildings along the Chicago River. Alternatively, take a sunset urban kayak tour and watch as the city’s finest architecture glows gold.

Located in Millennium Park, Cloud Gate (or The Bean, as it's affectionately known) is a vast public sculpture by the British-Indian artist Anish Kapoor. Made from polished seamless steel, this whimsical giant installation presents a distorted city skyline, with yourself at the middle of it. Next to The Bean you'll find another architectural landmark – Frank Gehry's curving Jay Pritzker Pavilion, a striking modern outdoor amphitheatre.

As the birthplace of house music, and a thriving jazz and comedy scene, there are plenty of things to do in Chicago once the sun goes down. Keep things casual with a foray into Chicago’s tavern culture, from prohibition-era institutions like the L&L Tavern to lively landmarks like the Old Town Ale House, established in 1958.

Chicago has 28 miles of shoreline on Lake Michigan, giving you your choice of silky sand and fresh water. The golden sweep of Oak Street Beach is popular with sunbathers, while Kathy Osterman Beach is the unofficial LGBTQ+ beach. Go kitesurfing at Montrose Beach, or paddleboarding and canoeing at 57th Street Beach.

Chicago’s Wicker Park and Bucktown neighbourhoods retain some of the creative edge they had back when High Fidelity was shot there in the early 2000s, but most of the city’s hipsters have now moved to Logan Square, with its thriving community of artists and musicians. Go for the lively Sunday farmers’ market, eclectic eateries and independent boutiques.

This red-roofed shack by the 95th Street bridge has been hot-smoking fish since 1948, when brothers-in-law Sid Kotlick and Len Toll opened this Chicago attraction on the Calumet River. Order the salmon with pepper and garlic, which is smoked overnight in the little wooden smokehouse next door.

It wouldn’t be a proper Chicago holiday without catching a baseball game. You’ll have to make a key decision, though: will you be a White Sox fan at the Guaranteed Rate Field, or will you don a dark blue jersey to support the Cubs at Wrigley Field? Either way, the atmosphere will be electric.