Musician Kurt Elling’s insider tips on his hometown Chicago

The Grammy Award-winning vocalist recommends cultural highlights in the Windy City
I live in New York now, but I still love Chicago – it's my hometown. In Chicago, I feel like I know the stories, where the ghosts hang out, and I don't get that in Manhattan. I'd say to anyone visiting for the first time that it is visually glorious. If you are interested in architecture, you've got Mies van der Rohe, Frank Lloyd Wright, the Bauhaus stuff, Louis Sullivan (who mentored Wright) and the Chicago Seven, who created the modern skyline. The Chicago Architecture Foundation on South Michigan Avenue runs walking or – even better – boat tours down the Chicago River and you'll get a great feel for the city's history.

My favourite building is probably the Tribune Tower, at 435 North Michigan Avenue, the neo-Gothic home of the Chicago Tribune. Colonel McCormick, who owned the paper, was a little like Lord Elgin – he got the foreign correspondents to chip out parts of famous monuments, which were then shipped back and incorporated into the side of the skyscraper, so you can see chunks of the Great Wall of China, Hagia Sofia, Notre Dame, the Taj Mahal, the Parthenon and Angkor Wat. I'm not sure these guys always asked permission, but what the colonel wanted, the colonel got.

Once you've seen that, go across the street to the Billy Goat Tavern, at 430 North Michigan Avenue – a Chicago landmark of a different kind where, when I was growing up, you still had guys come across from the paper with inky hands and green eye-shades on. This was the go-to watering hole for the great newspapermen and the walls are covered in framed front pages. There's a story about how the goat – a real one called Murphy – was denied entry to the Chicago Cubs' home ground, Wrigley Field, with the result that its owner cursed the team and they've been losers ever since, even though they've since apologised.

Want to see jazz? You've come to the right city. I got my start at the Green Mill, at 4802 North Broadway Avenue, which was once a hangout for the likes of Charlie Chaplin – this was back when there was a Chicago film industry to rival Los Angeles'. Al Jolson, Billie Holiday, Ella Fitzgerald, Miles Davis and Coltrane have all performed there. It used to be owned by Machine Gun Jack McGurn and frequented by Al Capone – you can still sit in his booth, positioned so he could see both entrances in case of a raid. I played here every Wednesday night for eight years – it has a unique atmosphere and you'll hear fine music.

Downtown, the Jazz Showcase, at 806 South Plymouth Court, has been in operation since 1947 and still attracts the big national acts. On the wall, you can see posters from back in the day when, in a two-week stretch, you could hear Dexter Gordon, Count Basie, Herbie Hancock, Dizzy, the Mingus Band – man, you would have just moved in and never left. If you want something more local – no big names but real tight musicians – Andy's is right downtown on Hubbard Street. It opens at 4pm – early for a jazz club – and the music starts at 5. The food is simple but good.

Then you must drop in at Gene and Georgetti, at 500 North Franklin, a classic Chicago steakhouse that has the best lamb chops in the world. It makes my mouth water just to think of them. They're rubbed with some family-secret spices, then broiled at an incredible temperature. And beyond the chops, it has its own folklore. There are pictures of Sinatra, Bob Hope and Lucille Ball and past mayors and governors – before they got put in jail – on the walls. It’s where 'the guys' go, if you know what I mean. But don't get put upstairs, that's Siberia. Gene and Georgetti's is within walking distance of the Gallery District, the streets around Franklin and Wells – a whole area where you can just hop from gallery to gallery and see some beautiful art and sculpture for sale.

When theatre in the US gets mentioned, people think of Broadway and Off-Broadway. But Chicago has, per capita, more theatre performances on any given night than any place else in America. People put on shows in garage spaces, churches, beneath bars, above the bar, in the bar. It's not all world-class, but it's people going for it, writing original material, putting blood and guts on stage and sometimes in the audience. The theatre scene is one of the many under-heralded things about my hometown. The two venues to check first are, of course, Steppenwolf, at 1650 North Halsted Street, where you'll see edgy, contemporary shows, and the Goodman Theatre, at 170 North Dearborn Street, which is a bit more establishment. Beautiful space, too.

You shouldn't miss the new State Street. Sinatra sang “State Street, that great street”, and it's once more worth a stroll. Look in at Macy's, too, which still has incredible Tiffany glass-mosaic ceilings, and the former Chicago Public Library, now the Cultural Center, at 78 East Washington Street, which has the largest Tiffany glass dome in the world. Everything that happens in there is free, so it's a great one-stop arts centre.

Right across the street from the Cultural Center is Millennium Park and the Frank Gehry outdoor concert shell, with its distinctive acoustic trellis. Again, concerts there are completely free. It seats 4,000 but there's room on the lawn for another 7,000. So, in summer, pick up a picnic, maybe from The Berghoff, at 17 West Adams Street, a great institution. It's another glorious experience – but then, as you can tell, I think Chicago is full of them.

— Kurt Elling, for TheWeek.co.uk