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Chicago’s gay village remains camp fun amidst the Windy City’s delights

Attitude explores Chicago’s gaybourhoods, eateries and attractions.

By Simon Button

Chicago (Image: Chait Goli)

The first time I visited Chicago about a decade ago and stumbled into Sidetrack in the city’s once called-Boystown region, I thought I’d died and gone to gay heaven. Here was a bar with the most diverse of crowds singing along to videos of showtunes, shouting back at the screen Rocky Horror style, camping it up to clips of Streisand and Minnelli, and welcoming everyone with open arms.

Northalsted rainbow crossing, Chicago
Northalsted rainbow crossing (Image: Bryan Smith)

It was a communal lovefest of all things Broadway and West End via big screen musicals and a montage of Faye Dunaway’s Joan Crawford bitchslapping daughter Christine over and over again, and I felt I’d found my tribe.

Chicago, in general, turned out to be just as fun and friendly a vacation destination with all the pluses of New York (stunning architecture, high-end shopping, distinct neighbourhoods) without such Manhattan minuses as overcrowding, dirty streets, and so-so food at all but the most expensive eateries.

The Windy City (so nicknamed because of the breeze that blows in off Lake Michigan as well as the hot air supposedly espoused by its politicians when bidding to host the World’s Fair in the 1880s) has been calling me back ever since, but there’s been a big change since my last trip pre-pandemic. Boystown is no more, at least not in name.

One of Northalsted's pylons
One of Northalsted’s pylons (Image: Del Nakamura)

In 2021, in the spirit of inclusivity, the business association restyled it Northalsted, although many locals still call it the old name and a few name-bearing bollards remain. It’s the same place in spirit with as vibrant a gay scene.

Camp is not a dirty word in Chicago. As well as the ongoing showtune sing-a-longs Sidetrack hosts other events like Drag Race viewings, celebrations of divas like Whitney and Gaga, and dog-friendly themed parties. When we were there a screening of Hocus Pocus 2 was greeted with such screams of joy you’d think the Sanderson Sisters themselves had flown in.

Myself and my friend Kevin arrive in Chi-Town (another nickname that has stuck) by more conventional means. After an overnight stay at Heathrow’s Hilton Garden Inn – which has great soundproofing and runway views – to take the edge off an early flight we hop on what looks like a brand-new American Airlines plane where the wine flows freely and the comfort levels are way up on the economy class of old.

Writer Simon Button (right) with his friend Kevin
Writer Simon Button (right) with his friend Kevin (Image: Simon Button)

Light sleepers and stuck in our ways, we’ve opted for separate rooms in different hotels. Kevin checks into the Kinzie (coincidentally the first hotel I stayed in on my first Chicago trip, back when it was called the Amalfi) for our five-night vacation whilst my bolthole is the supremely luxurious Pendry, housed in the landmark 40-storey Carbide & Carbon Building.

Checking into a high-floor Tower One Bedroom Suite, my breath is taken away by views of the Chicago River and its iconic cylindrical Marina City buildings. I’m also wowed by the massive bed, an almost-as-big shower, incredibly comfy bathrobes, and the Art Deco stylings of the building itself. (One note of caution: The elevators are really noisy, so pack your earplugs or request a room away from the lift shafts.)

Tower One Bedroom Suite at the Pendry Chicago
Tower One Bedroom Suite at the Pendry Chicago (Image: Provided)

Built in 1929, this beautiful slice of historic architecture – which was an office block until it was repurposed as the Hard Rock Hotel in 2001, the St. Jane Chicago in 2018, and now the Pendry – is accented with gold leaf and was designed to look like a champagne bottle. It is only fitting, therefore, that we toast the start of our holiday with drinks on the outdoor terrace of the hotel’s tres chic Château Carbide bar, followed by dinner in the on-site Venteux brasserie.

Sliding into a cosy banquette in this most elegant of settings, we sample the warming French onion soup and steak frites before calling it a night as we have to be up bright and early for the Chicago Architecture Foundation Center River Cruise. This fully-narrated 90-minute tour is the perfect way to learn about the city’s history and marvel at the magnificent buildings in what is officially the birthplace of the skyscraper. (Take that, New York!)

The Pendry Chicago
The Pendry Chicago (Image: Provided)

After a fortifying drink at City Winery, which is on the Riverwalk and the ideal spot for people- and boat-watching, we head to the Skydeck at Willis Tower and cowardly crawl into one of the glass boxes that jut out from the building at a terrifying height of 1,353ft. “It’s better if you stand up,” a staff member tells us but sod that! The views (that’s a word you’ll be hearing from us a lot) are spectacular, if nerve-shredding, whether you stand or not; the queues not too daunting if you invest in a CityPass.

The pass is a great investment, since it also gets you into the world-class Art Institute of Chicago and the Shedd Aquarium among other attractions with a whopping 48 percent off. We’d also recommend purchasing Big Bus hop-on-hop-off tickets if your legs are tired from all the pavement pounding, with the running commentary a great way to learn more about the city’s history.

Another fun way to get around is the famous elevated “L” trains. After butching it up with a couple of beers at Park Grill in Millennium Park, in the shadow of the iconic Cloud Gate bean-shaped sculpture, we take the “L” to Andersonville. This formally Swedish enclave is home to a large LGBTQ+ population and has a lovely laidback vibe, with low-rise buildings, amazingly clean streets, and charming local businesses like Eli’s Tea Bar and Uvae – a wine bar and fromagerie where the tasting wines flow nicely and the fromage is to die for.

The Cloud Gate bean-shaped sculpture
Cloud Gate bean-shaped sculpture (Image: Bhargava Marripati)

We also pop into Replay, which attracts a diverse crowd and has sports games on constant rotation, as do many LGBTQ+ haunts in the States. The food is supersized and the portion of nachos that I order is bigger than my head. I’m almost in a food coma as we head to the Meeting House Tavern, another lively LGBTQ+ institution where the drinks are strong and the Halloween decorations during our October jaunt are gloriously over the top.

Northalsted is our port of call the next day and it’s buzzier and busier than Andersonville, more like London’s Old Compton Street and Manchester’s Canal Street – except most bars don’t open until around 3 pm in the afternoon and day drinking is more of a weekend thing. We manage to find some lunchtime lubrication though at D.S. Tequila Company, where the food is much fresher than the usual Tex-Mex fare and comes, like everything in Chicago, with extra-friendly service.

Skydeck at Willis Tower
Skydeck at Willis Tower (image: Amit Thakral)

Name change or not, Northalsted is proud of its history as America’s first officially recognised gay village as well as its place in the wider queer narrative. Dotted along a half-mile stretch of North Halsted Street are a series of ten steel ‘Rainbow Pylons’ adorned with plaques celebrating the likes of such notables as Alan Turing, James Baldwin, Harvey Milk, Keith Haring, Freddie Mercury, and disco legend Sylvester.

They’re well worth stopping to read as you explore the neighbourhood, which is also home to the Center on Halsted, a truly inspiring community hub that offers performance events, volleyball courts, cookery classes, group therapy, and rapid HIV testing.

Then, of course, there are the bars, which range from the unapologetically old-school Lucky Horseshoe Lounge (the go-to place if you want to see go-go boys in minimal attire) to the stylish Elixir Lounge via the young-skewing Roscoe’s Tavern and the all-encompassing Progress Bar.

Sidetrack isn’t just our favourite Northalsted spot, it’s one of our favourite places in the whole queer world. The staff are gorgeous, there are scores of bars to check out across multiple levels, the clientele is as diverse as it gets, and those sing-a-long musical sessions (so popular that they have them three times a week) are the most fun you could ever have with your clothes on.

Sidetrack bar in Northalsted
Sidetrack bar in Northalsted (Image: Provided)

The next day is a lazy Saturday spent nursing hangovers and shopping at the designer stores and high-end chains that line the Magnificent Mile. Well, more like window shopping thanks to the terrible exchange rate. After that it’s a leisurely stroll along the shores of the lake, dodging cyclists and rollerbladers and marvelling once again at the skyline, followed by dinner at Rosebud on Rush.

Part of a citywide chain but with its own unique charm, Rosebud is an Italian restaurant where the atmosphere is loud and lively and the portions are hearty. My 8oz filet steak is honestly the leanest and juiciest I’ve ever had and the tiramisu lives up to the Italian translation of ‘pick me up’, laced as it is with lashings of whiskey and caffeine. Our waitress Victoria is so upbeat you’d think she’d been mainlining the stuff.

We end the evening at Cloud Bar on the 94th floor of 360 Chicago, which was a bit understaffed when we were there but where a nightcap comes with more amazing views – even though we’re not brave enough to try out TILT, the enclosed-glass platform that tilts outwards some 1,000ft in the air.

Taking a ride on the Centennial Wheel at Navy Pier the next morning feels less harrowing for us acrophobics. Yep, you’ve guessed it: The views from this 15-storey version of the London Eye are amazing. And with its spotlessly-maintained boardwalk extending 3,300ft across the water Navy Pier’s mix of shops and restaurants isn’t as tacky as it sounds.

Deep dish pizza is a Chicago staple, so we stuff ourselves with stuffed crust pies at the Navy Pier branch of Giordano’s. Customisable mains take up to 45 minutes to arrive but, clearly freshly-made and not whipped out of the freezer, they’re worth the wait, especially if you’re a cheese fiend.

Chicago (Image: Chait Goli)

Talking of cheese, we spend the rest of our last full day at Sidetrack for another showtunes fix. A lovely barman named Jaime serves our drinks with a side order of small talk about Steps – a nice surprise in a country where the Brit popsters have never troubled the charts.

The next morning we do a bit more window shopping, then grab a farewell lunch at The Dearborn Tavern. Done out in stylish wood and tile, this very upmarket restaurant has the most delicious midwest fried chicken and a semifreddo and berries dessert that goes well with their own-brand gin.

The icing on the semifreddo is getting a business class upgrade on the return flight (Kevin manages to mask his jealousy as I turn left on the plane and he turns right), where I revisit the original Hocus Pocus on the flat-screen TV whilst dining on another tasty steak before grabbing a few hours’ sleep on the blissful flatbed – full of five days’ worth of fine food, a deluge of drunks and so many new memories of a city I have every intention of returning to as soon as possible.

Attitude was hosted by Choose Chicago and Pendry Chicago, with flights by American Airlines