“Please ignore that,”’ says Joe, all avuncular with his mid-length beard, cuddly vowels and slow-blinking eyes as he points to the ‘TRUMP’ sign attached to a building that’s piercing Chicago’s milky night sky. “He doesn’t speak for us, the bastard.”
Joe is driving us downtown from O’Hare, and in between expletives he’s humming along to a channel that plays songs on the mellow spectrum and is presented by someone who used to be in Kajagoogoo. I tell him to take consolation in the people on our side; the Russell Group of universities, people with good hair, Cher. Trump has people who use the word ‘ironical’.
We’re dropped at London House with a handshake – warm, surprisingly soft – and mine’s a corner suite complete with views that incite memes. London House is a stalwart of the Chicago hotel scene that does the sort of glamour that wouldn’t scare your Aunty Jean, and employs a strawberry blond on the front desk who comes with a twinkle in his eye. Breakfast’s on the street-side diner watching joers in go-faster Lycra whizz past carrying rucksacks loaded with their work gear. A woman and her daughter join the next table, the latter made up for Instagram rather than pancakes with syrup. She looks like she’s dipped her head in all of Little Mix’s makeup range and set it with Elnett, and somehow it’s appropriate with that TRUMP sign the size of Germany leering over her. The mother, knuckle deep in Es Benedict, clearly has MAC-induced PTSD. Our waitress catches the accents and asks if we’re going to do The Architecture Tour, which is capitalized for a reason.
Because you really have to do The Architecture Tour, which takes place on a boat, lasts about two hours, and glides gently along the Chicago River past the greatest hits of the world’s first skyscraper city as you kick back and feel erudite. Because buildings are as important as telly – and because Julia Roberts and Dermot Mulroney did it in My Best Friend’s Wedding and there’s a bar that’s open at 9am. Among the undulating grandeur of Chicago’s skyline – from fin de siècle gems in pioneering steel to handsome pre-war warehouses hurriedly being turned into coworking spaces via Mies van der Rohe masterpieces – Trump’s is just, like, plonked, like an obnoxious reminder of America’s ongoing nightmare. But still, lots of photo opportunities involving the middle finger. A friend told me he did the tour three days in a row high on pills and liquor, which is a whole other story.
Architecture really is a big deal in Chicago, and fans of Frank Lloyd Wright will be friin’ off to all the booty in this town. From his first family home and studio in Oak Park – then country, now suburb – to his newly restored Unity Temple where a nice elderly gay gentlemen will show you around and cry when he talks about how far gay rights have come in the States. You’ll probably cry too.
You’ll also probably cry doing The Legacy Walk over in Boystown, the latter being what it says on the tin. The former being ‘the only outdoor LGBTQ museum and education program in the world’, a mile-or-so of often startling, always moving bronze pylons along North Halsted Street, each dedicated to a pioneer of gay rights. There are the ones you’ve heard of – Wilde, Milk, Turing – and those you probably haven’t but should have, especially the African Americans who were fighting prejudice from all angles, namely David Kato, Audre Lorde, Alvin Ailey, Lorraine
Hansberry. An ongoing project and decades in the making, they’re also handy props against which drag queens who look like Patti Boulaye and boys in low-slung hot pants fresh out of the Lucky Horseshoe can enjoy a fag while learning things.
Boystown is the oldest gay district in America and is still your go-to for the gayest of Chicago times. North Halsted is your main strip, where the night’s itinerary is pretty much dictated by length of queue. Sidetrack – bars on top of bars via dancefloors and terraces and topless barmen rocking kicky braces and, what are we calling this, art? and massive video screens that only play showtunes of a Monday – boasts the longest, so we hang out at The Closet, waitin’, anticipatin’, drinkin’. Then at Progress, ditto. I think we swing by that (very) Lucky Horseshoe we mentioned, a strip joint of the highest order, but who’s to say.
From town (take Anish Kapoor’s Cloud Gate AKA ‘The Bean’ in Millennium Park as your centre of Chicago gravity) Boystown is twenty minutes in a
cab, though the metro is easy to navigate and penny pricewise (especially to the airport) and not very scary at all.
Millenium Park is arguably the best of the world’s millennial parks, with said fancy bean, a rather beautiful pavilion by Frank Gehry, a museum of art (The Art Institute of Chicago) that’s a fortune to get into unless you’re clever and get a very clever Chicago City Pass or are sleeping with Cherysh-with-a-y on coat check who’s saving for a trip to Lake Geneva (Wisconsin), and swathes of wildflowers and ornamental grasses that rustle in the wind and get attended by people in full Felicity Kendal-in-The-Good-Life garb. There’s also a restaurant, Park Grill, that does half price on Wednesdays (including booze!) that your mum will love.
So let’s say Boystown is Main Gay Street; in which case, Andersonville, near enough to walk to from North Halsted on a balmy evening, is Edgy Gay Street. Either way, there’s way more plaid and pulled jackfruit, and Clark Street – where you’ll find the (in)famous Hamburger Mary’s and its drag queens who give the best back-chat this side of Sandra Bernhard – is the centre of the action with its buzzy cafes and bookshops run by women who narrow their eyes when you talk to them. It’s all a bit more recherché than ye olde Boystown. Some of the street signs are even in Swedish.
From Andersonville, Hollywood Beach is even handier. Here you can bob for boyfriends in Lake Michigan, which does a good job of pretending it’s an ocean and works a Bondi vibe with its scrappy-cum-glamorous mid-rises peering over a stretch of sand giddy with good looks and booze hidden in Chilly’s bottles. As Chicago’s official gay beach, this is your go-to on sultry days – though that no-drinking policy really ought to be a matter for the police.
“Did you do The Architecture Tour?” asks a nice man in Speedos as he bobs in Lake Michigan while clutching a Chilly’s bottle. Newish model, onyx you might say, vodka by the tastes of it. “I love a good building,” he continues. “Though I am quite dominant in bed.” Which might just be my favourite segue of all time.