48 Hours in…Chicago


There’s a lot of bluster in the Windy City this year, proverbial celebratory bunting all over the place. Happy 20th Birthday, Millenium Park! Happy 35th, Buddy Guy’s Legends! Happy 50th, Giordano’s Pizza parlour! The long shadows cast by the gangster anti-heroics of Al Capone and his infamous mob have firmly set, replaced by a sunnier disposition where the cab drivers seem genuinely happy, all streets have a name and barely a bubblegum blot defaces their tarmac. Nature flourishes in its myriad of parks and the sale of spray paint was banned back in ’92 so graffiti is practically non-existent. 

Only about an hour’s flight further from London to Chicago as it is to New York, (roughly 9 and 8 hours respectively), Chicago comes across as a less frenetic, often more elegant, even more mature version of the Big Apple. It has a fascinating history and a cultural caché if not exactly to match, then certainly to compete, making it the perfect long weekend getaway. 

The saying ‘A river runs through it’ could well have been invented for the city and the absolute must-do starter on any itinerary is the Chicago Architecture Foundation Centre’s River Cruise for an introduction to the city’s diverse architecture. In 1871, an estimated 300 people died and 100,000 were left homeless by a three-day blaze that destroyed all of the city’s mostly wooden buildings. If this was a catalyst for the beginning of the new look Chicago, some argue the World’s Columbian Exposition of 1893 was what really kick-started the current architectural landscape, allowing many of the local architects to flex their design muscles and return some confidence to their beleagured home. 

In a relatively small space, Chicago now has the most visible, eclectic and impressive range of architectural styles in all of America, perhaps all of the world. Expect to see Mid-century Modernism, Contemporary, Post Modernism, Art Deco, Neo Gothic, Gothic constructions, all scratching the sky, all showing off to each other like virile teenagers. Expect designs by architectural giants such as Norman Foster, Mies van der Rohe and Frank Lloyd Wright. Expect to see a former tallest building in the world (the Sear’s Tower), expect to see a building with a large urn on its top, expect to see one shaped like a champagne bottle, expect to see a Trump Tower; it’s all here and it’s all fascinating. 

The Jay Pritzker Pavillion, Millennium Park (photo by Abel Arciniega @tequilagraphics)

Frank Gehry doesn’t have a building on the river area but he does have one in Millenium Park, Chicago’s most loved open space, coddled on the North side by Lake Michigan and on the South side by Downtown as if it was their proudest love child. The Jay Pritzker Pavillion is pure Gehry; brushed stainless steel curves and ribbons, man’s architectural swagger inspired by nature’s quest to survive. It houses a mixture of musical concerts and movies over the Summer and is located across the park from the world class Art Institute of Chicago.

The Art Institute’s collection is extensive and covers an array of art history. Almost a million square feet in size, it has four floors and is a haven to lose yourself in or indeed to get lost in for half or more realistically, a whole day. If the contemporary section is impressive but with the obligatory Warhols and Johns and Pollocks, one of the must-sees is the Claude Monet room. Housing about 15 of the French impressionist’s works, the majority vacillate between his lily paintings and his London paintings, (specifically, the Thames). There’s a sublimity, a seemingly easy beauty and at times an incandescence which is hard to resist.

The other must visit section (which proves to be something of an orienteering quest to find) is that of the Arts of the Americas. If Georgia O’Keefe’s Sky Above Clouds IV is compelling in its simplistic, childlike beauty, then Edward Hopper’s Nighthawks and Grant Woods’ American Gothic must rate as two of last centuries most iconic paintings. They’re both surprisingly delicate and small but hypnotic, too, and well worth the trip in itself. 

If all this high brow culture is a little overwhelming, then maybe it’s time to relax and take in a local beer brewery which, naturally, provides a tasting session as the tour progresses. Goose Island Beer Company is situated in Chicago’s West town. It was established by John Hall in 1988 after a few visits to the UK where he fell in love with the diversity of local beer. The tour is a whirlwind of scientific explanation and beer room bar stories.

Expect to hear about a Christmas tipple brewed from turkey’s testicles (Testic-ale), which, not surprisingly, was never made available for public consumption. Expect to hear about how Goose collaborated with local musical heroes Chance The Rapper, Alkaline Trio and the not so local Fat Mike from Run The Jewels. Expect to hear how one of their most successful ales, Lost Palate, was made as a favour to their barmen, Johnny, who, at the time, had been diagnosed with cancer. He’d lost his sense of taste but, for some reason, could still appreciate mango and cinnamon. No-one thought the fruity, sweet concoction would work but it did. Johnny’s currently cancer free and still serves behind the bar; his hazy IPA became one of Goose’s top sellers. 

If the tour’s free beer (three different half pints) makes you peckish, Chicago has a myriad of restaurants from which to choose. Much of the choice here is American ‘nouvelle’ cuisine but a stand out is more old school in style. Although a self-titled ‘luncheonette’, Dove’s is a diner in Wicker Park which also serves breakfast and, on Mondays, Fridays and Saturdays, dinner. It reminds me a little of the Nighthawks’ diner in fact, triangular as it is. It has a long bar behind which copious bottles of spirits glisten.

You can eat at the bar, or at elevated long tables, sitting on tall stools. They serve Coca-Cola in glass bottles, have a juke-box which plays breezy jazz and serve up Mexican twists on American classics. They also advertise a glass of rosé and a shot of blanco tequila for $11. This might not be the most obvious pairing in the UK, probably even less so in the South of France, but right now I’m wondering why I didn’t take that offer up. 

Another slice of old school Americana, quite literally, is Giordano’s, just down from the famous Chicago Cubs’ Wrigley Field. Chicago is renowned for – and proud of – its deep pan pizza and if you thought, like me, this would be a slightly unimpressive Pizza Hut type experience, you’d be very, very wrong. 

The pizzas are, essentially, pies. They’re two or three inches thick and all the ingredients are mixed in with a ton of cheese. Our waitress stands on a chair to cut the slices and stretches the cheese as tall as she can stand which is about a metre and a half. These things are death-defying. They’re probably banned in the UK. They encourage fans to wear t-shirts saying ‘I got stuffed at Giordano’s’. Not surprisingly, they’re actually very tasty, too. Don’t have starters, don’t order large. Or medium. A small deep dish is more than enough for two. Do let your inner glutton loose; it’s an experience you’ll not encounter this side of the pond.

If your jet-lag hasn’t beaten you and you haven’t fallen into a cheese coma, Chicago is renown for its musical heritage. Whilst the Blues and Jazz are more often associated with the Southern States, Buddy Guy’s Legends is thus titled for a reason. Buddy Guy is a legend. And so are a lot of his, err, buddies. Guy was, actually, born 140 miles North of New Orleans in Louisiana but moved to Chicago around his 21st birthday when he started as a session musician for Chess Records along with such other luminaries as Muddy Waters and Howlin’ Wolf. 

Guitars from more musical legends who Guy has influenced (Jeff Beck, Eric Clapton, Carlos Santana et al) adorn the venue’s walls, and if it does look like a badly lit miniature plane hangar in between acts, once the lights go down, the magic starts to pump. It used to be that Buddy would turn up unannounced at his venue and play a full set or just jam with some of the guests. At the age of 87, he finally hung up his guitar on 9th June, headlining the free Chicago Blues Festival at the Pritzker Pavilion, but Buddy’s legacy lives on at his venue – and who knows, maybe he will make another appearance the night you decide to go. What are you waiting for?!

Chicago has been voted Condé Nast Reader’s Choice Awards ‘Best Big City’ in the country in  for a historic seventh year in a row. For more information about the Windy City, including details of where to stay, what else to see and do, and to start planning your trip, please visit www.choosechicago.com.

Photos courtesy of Choose Chicago