theartsdesk in Chicago: Radical Invention in the Windy/Second City

On my previous trip to the Second City in 2009, the much-awaited Art Institute of Chicago extension wasn’t quite ready for visitors, but is now about to celebrate its first birthday, and it’s a treat. The Modern Wing adds 35 per cent more space to the Institute, bringing it up to a nice round one million square feet and making it America’s second biggest art museum after the Metropolitan Museum of Art in New York. It was designed by Renzo Piano, whose new wing (another glass-and-steel box) will be unveiled at the Los Angeles County Museum of Art later this year; he’s clearly the go-to guy for art museums, having previously designed the Pompidou Centre in Paris. He’s also, by the way, the same man who is about spoil my beloved SE1 in London with his Shard monstrosity, but that’s for another day.

It’s a fine space, a three-storey box with curtain walls of glass, steel framed with limestone pillars (pictured below), and it contains about 1,000 works of European and American art and design since 1900. It enables the Art Institute to consolidate its modern and contemporary collections for the first time (they had been distributed throughout the multi-building complex) and to present the works in an elegant and appropriate setting. It also provides new spaces for photography and media, architecture and design, temporary exhibitions and a large facility for education. And currently on the top floor there’s Untitled (Alliance), an installation by Roger Hiorns, the British artisti nominated for this year’s Turner Prize for his stunning and evocative Seizure (in SE1, as it happens).

After a prolonged tour of the new galleries, brimming with works that had lain in storage for years, I saw Matisse: Radical Invention, 1913-1917. It's a large (nearly 120 paintings, drawings and sculptures) and informative show that concentrates on five prolific years and the collaborative nature of his career. I enjoyed it very much, not least for the fact that I hadn't previously seen many of the paintings on display (from the Art Institute's own collection and from the Museum of Modern Art in New York), despite being a regular visitor to both venues.

The Modern Wing comes complete with a rather fine restaurant, also on the top floor, which offers views over Lake Michigan on one side and the city on the other. The panoramas are absolutely worth the 14 bucks the restaurant charges for a thimbleful of wine. No, really. You must go, but I recommend the free iced water they also serve. It’s delicious.

Museum officials say they have raised about $370 million, primarily from private patrons in Chicago, of the $385 million needed to build and run the Modern Wing. Major giving, particularly to the arts, is one of the many, many things I adore about America; a large number of donors remain anonymous, others are endearingly keen to have their generosity publicly marked (although it's only fair to note that gifts are often made in respect of dead loved ones). Such largesse means one can walk around an exhibition and see everything from a whole wing to a single wall space named for a donor; one day, in keeping with my less substantial but no less hard-earned income, I hope to endow the Veronica Lee memorial doorknob.

The Art Institute was partially rebuilt from the ruins of a devastating fire of 1871. Such nuggets may be unearthed on one of the dozens of tours devised by the Chicago Architecture Foundation (CAF), whose headquarters are just across the street from the Art Institute on Michigan Avenue. CAF is an example of another utterly beguiling aspect of American cultural life, a not-for-profit organisation of generous citizens, in this case those who wish to share their love of Chicago’s rich and innovative architectural history; CAF’s volunteer docents lead a staggering 85 different tours on foot, bike or bus, by boat or - rather excitingly - Segway.

Chicago is a wonderful destination for those interested in architectural history; it has a bit of everything - more than two dozen distinct disciplines from the mid-1800s onwards, including Classical Revival, Prairie School, Arts and Crafts, and, of course, Chicago (or Commercial) School. As an architect once told me, it pays to look up when you are walking around a city, and that is absolutely true of Chicago, filled as it it with some of the world’s first skyscrapers and beautifully decorated upper storeys. Many of the city’s buildings, I’m delighted to say, have been added to the National Register of Historic Places, although much had been lost (including the old Stock Exchange building) in more philistine days.

Chicago has thus been associated with some of the world’s greatest architects - Daniel Burnham, Louis Sullivan, William Boyington, Mies van der Rohe, to name a few. One mustn’t forget, either, another who left his mark on this city, but also on many others in the States - Frank Lloyd Wright, who trained in a downtown practice. Although there are several FLW buildings in the metropolis, his lasting masterpiece lies in Oak Park, a small town a short train ride away from Chicago, where several of his creations remain, many of them still the unique family homes he designed them to be. There’s a small and - of course - beautifully formed museum as well.

For a theatre and comedy critic, visiting Chicago is almost a pilgrimage, as it is home to the Steppenwolf Theatre Company and The Second City, two companies that have defined generations of American actors and comics. The Steppenwolf (founded in 1974, pictured left) is a collective of actors, writers and directors who develop new and innovative work for their two theatre spaces. It is most associated with co-founder Gary Sinise and early member John Malkovich, and you would not be wrong in thinking that the word “serious” could be applied to much of - well, most of - its output; personally, though, I love the Steppenwolf’s intellectual rigour, which is increasingly unpopular in American culture and which Broadway appears to have long since given up on.

Last week, incidentally, I saw Tarell Alvin McCraney’s brilliant In the Red and Brown Water at Steppenwolf, the original production of which I had seen at London’s Young Vic in 2008. There it had an inspired design - the stage was a shallow pool, a nod to the play’s Louisiana Bayou setting - but the Steppenwolf’s space constraints meant the play was performed dry, as it were, and I was grateful for an opportunity to do a compare-and-contrast exercise. London just nudged it in my view, although my companion (a Steppenwolf regular) was enchanted and thought the watery setting would have been offputting.

The Second City, who perform not far from the Steppenwolf in the Lincoln Park district, was founded in 1959 and has produced a prodigious roll-call of comedic talent, including Alan Alda, Joan Rivers, Gilda Radner, Eugene Levy and Mike Nichols. It could be argued - well, I’m arguing it - that Second City’s improvised sketch comedy led directly to an American television institution, Saturday Night Live - indeed many Second City alumni, including John Belushi and Tina Fey, were SNL mainstays for many years. Saturday Night Live continues weekly - or perhaps that should be weakly, as it is a shadow of its former self, with Fey's perfect renditions of vice-presidential hopeful Sarah Palin's idiocies in the 2008 campaign serving only to remind us of the show's witty heyday.

Although Chicago can't compete with New York in terms of theatre - many fewer houses, commercial and otherwise, and it gets Broadway shows only when they tour - it is nonetheless a city that loves the arts. And whatever your cultural preference, Chicago has a world-class presentation of it. Opera’s your thing? The Lyric Opera perform at the Civic Opera House, a smashing blend of Art Nouveau and Art Deco, under the musical direction of Sir Andrew Davis. Classical music - in September Riccardo Muti will take the helm of the Chicago Symphony (who, by the way, perform in a glorious 1904 hall of their own, opposite the Art Institute). Ballet - why, the Joffrey company is based here. And of course, the one art form that will for ever be associated with the Windy City, jazz, continues to thrive in venues large and small around town.

However arty this city is, though, I can’t send a letter from Chicago without mentioning its sports scene. This is a town as much in love with sport as the arts, if not more so, and whose sporting prowess produces as much drama, passion and intrigue as any play or opera. Chicagoans are obsessed with their basketball, American football, ice hockey and baseball teams, and where the last is concerned, the rivalry between the White Sox and the Cubs could have kept Shakespeare busy for decades. A sports-obessed, art-filled city: could you ask for more?

• Matisse: Radical Reinvention 1913-1917 until 20 June