Travel: John Howard explores the gay-friendly Chicago

When it comes to America’s gayest and gay-friendliest cities, Chicago is right up there with San Fran and New York. Travel writer John Howard explains why.

There’s a naked man walking about on North Halsted Street and no one gives a rat’s arse (except to get their photo taken with him, that is).

We are in Chicago for Market Days, a gay street festival where the visible penis lines tucked into shorts are so numerous they’re going to have someone’s eye out if they’re not careful. It’s not a naughty Folsom Street-type event, but no one told the tall ginger bloke with just a bandana tied round his cock and balls.

North Halsted is the beating heart – and beating jockstrap if you set foot into the Lucky Horseshoe strip saloon at its centre – of Boystown, the actual name of the area and the oldest gay district in America. And it’s official. They even have the Legacy Walk, a series of rainbow-painted pylons lining the street that tell the gay stories of gay folks from Oscar Wilde through Alan Turing to Keith Haring. It’s quite an education (they actually reckon that the best-informed gays in all of Boystown are smokers, who get to read the potted biogs when they pop out for a fag), but even the well-meaning folk from the gay centre who put them up are under no illusions about what’s drawing guys down here. It’s the bars and the boys.

When we jump a group of local gays having dinner at an art gallery/warehouse/restaurant/club to ask which of the many gay drinkeries in Boystown to go to on our first night in town, they tell us to just get in the shortest queue. They probably said ‘line’, but we’re paraphrasing.

The longest queue is undoubtedly for Sidetrack, a massive labyrinth of a place with snooky bars and terraces and dancefloors and video screens (it’s all musicals all the time on Mondays), which attracts a mixed crowd of boys and their girls of most ages, colours and types. But there are also lines for Progress right next door and The Closet. We start with Progress, so we can survey the queue for Sidetrack which we wangle our way into later on.

For food, try the Chicago Diner, a classic American diner with classic American diner portion sizes, the only twist being that everything there is plant-based. Yes, vegan! They’ve been going for 30 years so it’s not bandwagon-jumping and they must be doing something right to have lasted that long.

Boystown isn’t exactly handy for town proper – around $15 in an Uber from Millennium Park – but it is fairly handy for Hollywood Beach, the clothing-optional sandy stretch of Lake Michigan (well, we’re assuming it’s clothing optional: we saw plenty of peen) where you can stand in the water in your Speedos and wonder how this doesn’t count as a sea (bring your own booze, by the way as there’s nowhere sells it down there).

It’s also fairly handy for Andersonville, a hipster-ish gaybourhood with lesbian bookshops and gay bars and buzzy little brunch spots like Big Jones, where you get served up Southern treats in very big portions with some signature cocktails that went down way too easily after our big night out in Boystown. Clark Street is the main shopping drag with gay bars like Atmosphere and Marty’s Martini Bar just off the main road. The crowd around here is – how to put this? – maybe older, maybe wiser, maybe wearing more clothes than the scamps down in Boystown, but there’s plenty of fun to be had at places like Hamburger Mary’s right there on Clark Street, where the burgers are cheap, the booze never stops coming and the weekend drag shows are absolutely hilarious: we saw a trans Whitney Houston in a sheer top and a 300-pound Patti LaBelle.

But, though you’ll want to gay it up in those areas, you do need to get into town proper because it’s pretty spectacular, especially if you get a high-up room ending in the numbers 31 at LondonHouse hotel, which looks right over the river and the oldest living skyscrapers in the known world. You’ll selfie yourself into a frenzy against those windows and the rooftop bar is also pretty spectacular, but there can be quite long queues in the hotel lobby to get up there if you’re not a guest.

Even if you’re not that into architecture, which is definitely Chicago’s specialist subject, it’s worth taking one of the architecture boat tours along the Y-shaped river as it not only orients you and gives you some ideas for riverside drinking by water that is clean and green and rocking with everything from yachts to kayaks, but it also has a bar right there on board.

And if you really are into architecture, then clever old you for coming to Chicago. Not only does that boat tour show you a potted history of American buildings from Italianate sky-scrapers through Mies Van Der Rohe modernism to the present-day Trump Tower, which is actually not that bad apart from the big ‘Trump’ on the front, there’s also some great Frank Lloyd Wright to see (skip this bit non-architecture fans: his studio, his house and his temple – all early modernist masterpieces – are in the suburb of Oak Park).

For everyone else there’s Anish Kapoor’s amazing reflective bean in Millennium Park, a large slab of open ground with a Frank Gehry (more architecture!) auditorium, some beautifully planted wild grass and the impressive Art Institute of Chicago (with an extension by Renzo Piano – the architecture seriously never stops coming).

This is all a five-minute walk from LondonHouse and if you’re looking to stay, check out the extraordinary Chicago Athletic Association, a hotel fashioned from the city’s old gentlemen-only members’ club right on the edge of Millennium Park. Reeking of masculinity, they’ve kept it all really old-school from the massive first floor lobby, all dark wood and open fires to the huge games room next door, where you can put your name down for billiards or bowling while you sink a beer. The no-window restaurant right at the back (there were windows but they had them bricked up back in the day so no one could see what was going on inside), is also worth checking out.

They say that Chicago is like New York but without the arseholes and it’s true that it does feel more like Canada, which, let’s face it, is just over there. It’s friendlier, cleaner and has its own particular buzz, which may feel small-town but in a totally lovely way. I mean, you can’t go wrong with seriously friendly people. Especially if they’re walking around naked.

Thanks to
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