You’re always guaranteed a great time in Chicago. This Midwestern city, the USA’s third largest, has a lot to shout about: from piercing skyscrapers to scenic lakeside beaches, welcoming bars to iconic and indulgent eats. This three-day itinerary takes in all the hits, and then some.

You’ll want to spend your first day in the Windy City ticking off the big hitters – because after all, they’re popular for a reason. Rise early and head to the beloved Millennium Park to explore the art installations and snap your photo with the iconic Cloud Gate (aka the Bean) sculpture. Next, it’s an easy walk to the Art Institute of Chicago, the city’s hulking and historic gallery. Here you can see American Gothic by Grant Wood – it’s a local favourite – as well as Georges Seurat's A Sunday Afternoon on the Island of La Grande Jatte – which you might recognise from the film Ferris Bueller’s Day Off.

Once you’ve had your fill of art, it’s time for some food. Stay central, ambling along Chicago’s gorgeous Riverwalk before you reach Beatnik on the River. Aim to bag a seat on the terrace here for stunning views of the skyscrapers. The food’s equally stunning: opt for a weekend brunch to indulge in everything from bao buns to shakshuka, oysters to avo on toast. Afterwards, you can walk off your meal along the Riverwalk or why not stay at Beatnik for some late afternoon cocktails? They’re dangerously delicious.

Make your way north towards Old Town as evening approaches. On your way up, stop for dinner at either Portillo’s (for classic Chicago hot dogs) or Giordano’s (for a taste of the city’s famous deep dish pizza). Next up: comedy. Modern improv was first devised in Chicago and alumni of the city include Adam McKay, Tim Meadows and Tina Fey (to name a few), so it’s fair to say this place knows how to make the people laugh. Old Town hosts a cluster of comedy clubs, including the city’s most famous, The Second City. A show here makes for a fitting end to your first day in Chicago.

On your second day, venture west to Wicker Park. This is Chicago’s original hipster hub: picture rows of achingly cool record stores, characterful vintage boutiques and quirky coffee shops. Though the area has since gentrified – and neighbourhoods like Avondale and Pilsen now have the edge – Wicker Park is still a magnet for alternative shopping. Spend a leisurely morning browsing the shops (Asrai Garden, Myopic Books and Reckless Records are our favourites).

Chicago is a sports town through and through, and catching a game here (whether it’s baseball, basketball, football…the list goes on) is always an event. If you can’t get tickets, take a tour of Wrigley Field instead. This historic baseball field, home to local legends the Chicago Cubs, is a landmark of Chicago’s sporting prowess. On a tour, visitors can see the field up-close and spot throwback touches such as the manual scoreboard.

A hop, skip and jump from Wrigley Field are Lakeview and Boystown – two of Chicago’s favourite nightlife spots. Be sure to line your stomach at the Chicago Diner before you head out, though. Vegetarians are in good hands here: this old-school spot has been meat-free since 1983. Once you’ve had your fill of green cuisine, it’s time to hit the bars. Boystown is Chicago’s LGBTQ+ nightlife hub, with fun-loving and always-inclusive clubs like Scarlet Bar, Berlin and Sidetrack all ready to party when the sun goes down.

Look south to the neighbourhood of Hyde Park on your final day in Chicago. This lively student area, the stomping ground of the University of Chicago, features some of the city’s best museums. There’s the DuSable Black History Museum, which provides a deep dive into the area’s African American history, and the Smart Museum of Art, Chicago’s hub of modern art. Around the university you’ll also find Frank Lloyd Wright’s famous Robie House – a stylish example of Midwestern architecture. The Plein Air Café next door is a lovely spot for lunch.

Hop on the train to the South Loop as the day goes on. Here you can amble along the Lakefront Trail, a scenic path that sweeps up the shore of Lake Michigan. If the weather’s behaving, unwind at 12th Street Beach and take a dip in the water here. Or, if you’re hungry for more culture, the Field Museum is another world-class player on Chicago’s museum scene.

For your final evening in Chicago, tick off two of the city’s greatest loves: skyscrapers and blues music. The world’s first skyscraper was built in Chicago and the city invented its own version of the blues (largely thanks to Muddy Waters). Head to the Willis Tower, Chicago’s tallest building, for stellar views of the city’s shimmering lights. Back on ground level, make your way to Buddy Guy’s Legends – perhaps the most iconic blues spot in the city. Book a ticket for a show here and settle in for an unforgettable evening of music. Hungry? Don’t fret, there’s New Orleans-inspired food on offer, too.

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