Fending off jet lag, I take my seat in the Upstairs Theatre at Steppenwolf in Chicago's Lincoln Park neighbourhood. Bypassing the "party-zone seating" in favour of the auditorium's outer rung, I duck under a low-hanging disco ball as the house lights dim. My heavy-lidded eyes lock on to actor and co-writer Tarell Alvin McCraney (who won a screenwriting Oscar for Moonlight in 2017) as his character, Joan Jett Blakk, utters her opening lines. Set in Chicago in 1992, the play, Ms. Blakk for President, is the true story of America's first black drag-queen presidential candidate. Part campaign rally, part nightclub performance, the show more than negates my weariness. A pronounced thespian, my quickest route into any city is through the stage door - and a fringe venue is always preferable. In these civic spaces, important conversations relevant to both the local community and the city's wider intake are platformed, and the audience respond accordingly.
From McCraney's presentation of queer politics to Chicago's newly appointed mayor, Lori Lightfoot (Chicago's first openly gay, African-American female mayor), the current conversation seems to be one of change and equality. In a "divided we stand" America - gridlocked over social issues, gender, race and the economy - political polarisation has peaked. Like many large US cities, Chicago is a Democratic island amid a sea of red. The city has a long-running history of gun-fuelled neighbourhood crime, with a deepening divide between the haves and have-nots and growing tension around gentrification. Still, Mayor Lightfoot's election feels like progress. The homicide rate is beginning to fall and many of the city's civilians - namely creatives across the fields of music, art and design - are opening up the conversation and re-examining the divisions that make it hard for Chicagoans to see one another as neighbours. In Chicago's more low-key neighbourhoods, art and activism are thriving and forging a new sense of the city's identity.
My hotel, the recently opened Hoxton, Chicago, lies in the West Loop locale, where a community of WeWorkers and Googlers who grab coffee at Soho House and spin at Soul Cycle make me feel that I could be at any number of hipster hotspots around the world. Populated by third-culture kids wearing workout gear to brunch, this gentrified ground feels disparate from the more troubled Chicago I've read about prior to my arrival. In bed I read the opening paragraph of an essay about local gallerist Anna Cerniglia of Johalla Projects. She was brought in by the Hoxton to curate an array of artwork spotlighting "the creative reach of Chicago's art community". I stretch for my duvet, which a pamphlet informs me is dressed with custom bedding by artist Cody Hudson, and pull it close to my chest in preparation for a day of exploring the art community that Cerniglia namechecks.
The next day and across town in Little Village, I've arranged to meet with artist Maria Gaspar. As with most cities, the areas in which artists base themselves here tend to be the next on a list of up-and-coming neighbourhoods. Made up of some 77 community areas - each as dynamic and diverse as its inhabitants - the city could easily feel segregated and territorial.
Yet such lines are beginning to blur. Formerly off-the-beaten-path neighbourhoods such as Humboldt Park, a traditionally Puerto Rican enclave, and Pilsen, a predominantly Mexican area, are morphing into hipster hinterlands flanked with concept stores, artists' studios and cool eateries. More importantly though, it's in these areas that some of the most interesting ideas shaping the future Chicago are being fostered. Just west of Pilsen, Little Village was originally dominated by a Czech community before Mexicans (including Maria's family) moved in in the 1960s. Today creatives and artists are taking up residence. For Maria, that's merely a happy coincidence.
Maria's long-term work, the community project 96 Acres, is rooted 10 minutes by car from her studio at Cook County Jail. Keeping things "in the neighbourhood", Maria's practice is community-led. She was first introduced to the prison as a child as part of the Scared Straight Programme, for which her school felt it necessary to pick out all the "brown kids" in the class and bring them here. The plan has "backfired'', she jokes to me. "I've ended up in prison anyway" - although in a different context. Named after the size of the Cook County Jail - the largest single-site jail in the US - the 96 Acres Project aims to dissolve the boundaries of the prison through small, subversive acts. Each week a self-selected group of prisoners referred to as an "ensemble" uses its shared time to read poetry, create art pieces and express opinions. Leaving Maria's studio, my vantage point of the area has shifted.
In a continued effort to eschew the city's tourist-trodden avenues, we decide to stray further beyond the Loop to meet two notable artists, Kerry James Marshall and Theaster Gates, who share a focus on the loaded word at the tip of my tongue - and that of many Chicagoans, it seems - "community". Originally from South Central Los Angeles, artist Kerry James Marshall has lived in Bronzeville for 25 years and counting. His works are immediate responses to the area in which he lives. Including the fantastic and the ordinary, almost everything Marshall depicts has taken place in Chicago.
Twenty years ago, a plan to transform the Douglas area saw the tearing down of the high-rise public-housing unit Stateway Gardens. This vertical ghetto was plotted on the "State Street Corridor", said to be the largest concentration of public housing and poverty in the US, and its demolition brought with it a new set of problems for the neighbourhood and its displaced residents. In response Marshall created "Many Mansions". Realised in overlapping vignettes, it depicts scenes and actions that "probe at our capacity to convert the environment we are living in". The artist's works are forms of social commentary riddled with irony. They also come endorsed by Sean Combs, the artist most recently known as Diddy, who acquired Marshall's monumental painting Past Times for $21.1 million at Sotheby's in 2018. The artwork - a take on a pastoral scene typically filled with European aristocrats - depicts a black family engaged in high-class leisure (golf in the forefront, waterskiing further in the distance).
Situated on the perimeters of the city, the social and economic positioning of Bronzeville and other areas like it is an intractable problem. American architect Daniel Burnham created what we now know as urban Chicago, in which social disenfranchisement intensifies in the suburbs. Setting everyone to the outer rung, "this model is not acting on behalf of equity," according to Theaster Gates, who is based in Stony Island Park. "We're all learning wrong". Indebted to his community, he (like Marshall) is intent on staying in the area, despite having the financial means to move wherever he chooses. Roots run deep here.
At a time when America is fighting for its place in the world, Chicago is reassessing its foundations - and its architects are a fundamental part of this change. We pull up outside Studio Gang on Division Street, where the architect Jeanne Gang is based. Listed in this year's TIME 100 list, Gang has won the bid to design the new global terminal at Chicago's O'Hare Airport. For context, Gang's scintillating Aqua in Downtown Chicago is the tallest building ever built by a woman. Now she's building an even taller one.
However, phallic structures in the sky are certainly not the ultimate objective for Gang, who views architecture as "a catalyst for change". Her Polis Station concept, launched at Chicago's inaugural Architecture Biennial, fused police stations with civic recreational centres in an attempt to improve the way civilians interact with law enforcement. Testing the idea in one of Chicago's most violent neighbourhoods, Gang Studio added a basketball court to the 10th District police station in North Lawndale. Gang has also designed boathouses which filter run-off organically to help revive the polluted Chicago River. Whether aimed at "honeybees or humans", the studio's projects are always viewed as places for habitat, and the airport will be no different. In what will be the first US terminal to have both domestic and international terminals come together, its design is another indicator of the city's desired cohesiveness.
Shouldering neighbourhoods Boystown (one of the largest LGBT communities in the Midwest) and Wrigleyville (home to baseball team the Chicago Cubs) are an anomaly in the city. These two contrasting communities seem to coexist with relative ease, and I'm surprised to happen upon such cohesion en route to the Cubs-versus-White Sox game. Knowing less than nothing about baseball, my only reference is: "it's the bottom of the ninth", meaning it's almost over. Baseball is a honeypot and a lifeline for the community, and local businesses have converted their rooftops into bleacher-style seating to accommodate the overspill of fans keen to catch the game. After four innings I order a hot dog with all the trimmings and manage to get mustard on my t-shirt while, further along our row, two very vocal - and very lubricated - friends rooting for opposing sides passionately hurdle abuse and advice at the players, each other and anyone within a one-mile radius. We join the chorus of William Hung's Take Me Out to the Ball Game - "Let me root, root, root for the home team, if they don't win it's a shame. For it's one, two, three strikes, you're out, at the old ball game." The Cubs lose 3-1. Shame.
RSVP'ing "no" to tailgating (where food is served from the back of a parked car after the game), we instead catch the tail end of a pop-up at the Lost Girls Vintage store on West Chicago Avenue. Run by three friends, Lost Girls Vintage exemplifies many of the traits I've come to associate with Chicago: it's idiosyncratic, politically aware and, of course, community-centric.
Five minutes spent in this cavern of leopard print and fuchsia- hued fringe, and I'm seduced. Acid-lime cowboy boots in hand - this is the Midwest after all - I approach the till, which is (wo) manned by one of the owners, Sarah Azzouzi. After relinquishing the aforementioned cowboy boots to my care she rattles off places to shop, chill and hang out in the evenings. The list reads like a menu of habitats for free-spirited, gender non-conformists - though I am neither, Azzouzi assures me I am still very welcome.
Reading through her recommendations, Kokorokoko (a vintage store stocked with finds from the 1980s, 1990s and y2k) and the woman-owned "boho biker boutique" Tarnish both appeal. We head first for Humboldt House, a community shop filled with the work of local and emerging Chicago makers. Plotted in the artist-centric neighbourhood of Humboldt Park, this community- oriented, feminist shop serves as an incubator for work and ideas - at least, that's how owner and art-grad Claire Tibbs sees it.
I somewhat sceptically purchase two rods of selenite to cleanse my jewellery, as well as a mug depicting wayward breasts, before nodding in agreement at the sign above the exit which reads (in rainbow lettering): "In this house there is no racism, sexism, homophobia, transphobia, xenophobia, ageism, body shaming, white supremacists, Trump apologists".
I'm expecting more sharp-tongued social commentary that night at The Second City on West North Avenue, where I'm hoping to witness the next Bill Murray or Amy Poehler (spoiler: I didn't). The Second City theatre ostensibly does social and political satire, but what I encounter is rather sillier. A no-script policy lends to a lot of drivel churned out on stage, although there are a few glimmers of brilliance. Tackling controversial topics one by one, a line of comics riff on recent encounters in the city and further afield. Quick-witted, sassy and opinionated, their off-the- cuff observations match up with many of my own impressions of the city.
The sketch comedy seems to have rubbed off on me and despite my best intentions, I succumb to a day of "yes". First stop: Millennium Park. Here I (briefly) engage with a community of narcissists scurrying to catch their own reflection in Sir Anish Kapoor's Cloud Gate. Having been there, done that, we do a loop of the park and pause at Crown Fountain, designed by Catalan artist Jaume Plensa and executed by Krueck + Sexton Architects. Ankle deep in water, I am surrounded by gloriously gleeful children readying themselves for the next spurt of water to gush from the fountain's pursed lips. The park - a popular and populist place - has won me over.
Back in my own mini city of repurposed warehouse spaces, Aesop stores and Whole Foods, I nab a seat among a crowd of LED-illuminated freelancers. I consider the places I've been, and draw out my phone to count the geo pins I've plotted on Google Maps: 76. I've covered a lot of ground this past week. It's been a circuitous journey, but I've largely succeeded in my aim to circumvent the tourist route, worthwhile detours aside.
Seeking alternative entry points to the city by favouring design and social practice over skyscraper observation decks and deep- dish pizza has paid off. I've been made to feel part of various communities and welcomed as an observer in others. Looking inward, seeing outward and moving forward (and probably upward), it seems that in Chicago artists, politicians, architects, prisoners and playwrights are assessing the ground from which we take our bearings and are laying the foundations for a new era.