We found three standout ways to see the city. First, climb one of its tallest buildings – as well as the Willis Tower’s Skydeck with its glass-bottomed Ledge, the John Hancock Center has TILT, which leans you 30º out over the edge of its 94th floor.

Then take a CAC River Cruise. In their shadows at water level is where you can find out most about the skyscrapers all around you. Our expert guide used the buildings on the river to tell a captivating story of how the city got from early Beaux Arts relics and Art Deco beauties to the post-modern statements being made in glass today. 

Now jump on one of the old Brown Line ‘L’ trains that still clatter around the Loop, snaking around the feet of the downtown skyscrapers. The elevated railway didn’t just give the Loop district its name. It gives Chicago its sense of place – which is why you see it in so many of the classic films set here, from Planes, Trains & Automobiles to The Fugitive and Ferris Bueller’s Day Off.

One of Bueller’s best moments is in the Art Institute of Chicago. It remains a world-class museum with iconic paintings like Nighthawks and American Gothic. Pushed for time? Follow Bueller’s route through it and you’ll also catch big hitters from Pollock, Chagall and more. 

For serene contemplation of a different hue, the Chicago Bath House is where Capone used to get a sweat on. Fashioned out of an old factory, Aire is a contemporary alternative with appealingly industrial stylings. Right opposite the Bath House in Wicker Park, Independence is an on-point menswear store doing a nice line in American brands that can be hard to come by back home. It’s a good spot to get to know Randy’s Garments, John Gluckow, Wythe, Dehen 1920 and others in person – the boys inside are also generous with their bar recommendations and local tips. Nearby Saint Alfred leans more into streetwear, as does Notre over in the West Loop.

And then there’s the sport. The Bulls and the Blackhawks share the United Center, where Jordan won three of his six NBA rings. When the Bulls are playing, mascot Benny the Bull does tireless work hyping the crowd, with co-ordinated support from the jumbotron that hangs from the ceiling. The Bulls today are not quite what they were in Jordan’s day (no team is really), but the quintessentially American experience they lay on remains hard to beat. For more about the classic Bulls team, the Sports Museum – right next to the Willis Tower – is a fun place where you can compare your wingspan to Scottie Pippen’s, and finally put to bed any lingering doubts about whether you might have made it in the NBA.

With the Bulls’ hardwood court swapped out for an ice rink a couple of days later, the Blackhawks game we caught flowed smoothly. After a famously rousing version of the national anthem, the only punctuation came from the crash-bang sounds of the local boys and the Pittsburgh Penguins charging each other into the side boards, then the celebrations of a 3-1 home win.

Any cricket fan will appreciate the rhythm and beauty of a sunny afternoon at Wrigley Field. Each year, the return of baseball announces that summer will soon be here. The gentle, early-season buzz around the historic ground was about Cubs newcomer Kyle Tucker, but this was veteran Ian Happ’s day – an astonishing catch marking his thousandth game as a Cub. As the home fans celebrated a 7-1 win over the San Diego Padres, we were left to wonder why you can’t get beer and hot dogs delivered to your seat at the cricket. In the likely event of leaving the ballpark wanting more, surrounding Wrigleyville is well set up for baseball fans – among the sports bars and merch shops, Big Star is the place to make the switch from dogs to burritos. Wrigley Field is the first place we’d go back to on any return trip to Chicago, but if you have a weakness for an underdog, head to the city’s South Side and catch the White Sox at Rate Field.

For the first time in a while, American football’s Bears might be the team the city is most excited about. Caleb Williams is a talented young quarterback with a high ceiling – and this year the Bears have a new head coach who might just be the one to unlock Williams’ potential when the NFL season starts this autumn.

For a greatest-hits city break, the Loop location of the Chicago Athletic Association Hotel is hard to beat. Anish Kapoor’s shiny, perception-warping Bean sculpture is across the road in Millennium Park, next to the Art Institute. Built in a Venetian Gothic style, the hotel itself was once a gentlemen’s sporting club. It’s moved with the times, but retained the superbly indulgent interiors the gents chose for themselves. With three working fireplaces, the lobby exudes a sort of homely decadence, and there’s a sprawling games room and bar just off it. Up top, Cindy’s is the property’s sole new addition – its views make the update worth it. Bedrooms are spacious, comfortable and in a manly palette the boys of yesteryear would recognise and appreciate.

The city’s more familiar accommodation options include a Soho House and The Hoxton, a couple of blocks from each other in the Fulton Market District. Both are within striking distance of Au Cheval, the restaurant that might do the city’s finest cheeseburger. For international luxe, there’s the Peninsula, halfway up the Magnificent Mile that runs north from the Loop. Right on the Chicago River, the Langham occupies a masterpiece building from the great modernist Mies van der Rohe.