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Boys, boys, Boys(town): Why Chicago is one of the world’s most amazing cities

Written by gaytourism

Are you looking for a full-fat, high-rise, all-American city break that’s super LGBTI-friendly to boot?

Then look no further than Chicago.

As I discovered on a recent visit, the Windy City has all the ingredients of a blockbuster metropolis, but they’re cooked to an alternative recipe.

Photo credit: Pixabay

The largest city in Illinois has a unique feel: it’s gritty and glam at the same time, with a real American flavor.

It’s somewhere everyone should taste at least once. Here’s all you need to know for a perfect long weekend…

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Look at the buildings

Chicago’s architecture is awe-inspiring. It’s the sort of cityscape the forefinger-to-thumb, ‘perfect’ emoji was created for.

With everything from art deco to contemporary, you could spend a lifetime staring at it.

The trick is to see it from above and below, so you really appreciate the contrasts.

From above, you’ve got two options. First, head to The Willis Tower, the second-tallest building in the Western Hemisphere. (The One World Trade Center in New York City overtook it in 2013).

It’s a nosebleed-inducing 108 stories tall, and the Skydeck on floor 103 offers some cracking, all-encompassing views of the skyline, and also the vast Lake Michigan beyond.

On a clear day you can see into Michigan, Indiana and also Wisconsin.

The highlight (emphasis on ‘high’) is the ledge; two all-glass viewing boxes that abut from the main tower.

Looking down is a challenge, but once you’re on it, the experience – the feeling that you could be a bird – proves more than an adequate distraction.

The second option is 360 Chicago. Situated in the John Hancock Center on Magnificent Mile (the city’s shopping Mecca), 360 offers more knock-you-off-your-feet views of the horizon.

If you plump for this option, we’d suggest making your visit in the late afternoon/early evening as there’s a lovely little cocktail bar at the top.

Plus the alcohol will make for a bit of Dutch courage should you brave The Tilt, a scare-yourself-senseless ‘ride’ where you are titled – on a giant windowpane – 30°.

You’re left feeling like you’re hanging in mid-air. It’s a far more terrifying sensation than the Willis’ ledge, so it all depends how brave you’re feeling…

Roll on the river

To appreciate Chicago’s architecture from less lofty heights, get yourself onto the relevant trip with Chicago’s First Lady Cruises.

Over a leisurely 90 minutes on board, you’ll absorb the history of the city’s skyline from a distinct perspective. It’s probably the only way to take in the sheer variety of architectural styles that pepper the banks of the Chicago River.

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Do the boat tour and at least one of the towers on the same day; the context from one will enrich your experience of the other.

If this still hasn’t sated your architectural lust, jump on the L Train (Chicago’s subway) and head out to Oak Park.

This absolutely stunning historical suburb has the largest concentration of Frank Lloyd Wright buildings in the world. Many are private homes, so you might not be able to nose inside, but they’re just as gorgeous from the outside.

Meanwhile Lloyd Wright’s family home and studio are open to wander round, and it’s all the #interiorsgoals you could ever want.

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Picnic like it’s 1999

Millennium Park, nestled on the shores of Lake Michigan – in the heart of Downtown – is Chicago’s 25-acre space for public art.

It’s of course the home of the world-famous Bean [pictured top], also called Cloud Gate. This is the mirrored Anish Kapoor sculpture that is the subject of countless Instagram posts. But there’s so much more to see than that.

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Go and stare at Crown Fountain, and be awed and slightly perplexed by the combination of digital videography and water. Lots of water, actually. We challenge you not to run through it on a warm day.

Check out the Lurie Garden too. It’s beautiful, and has a slightly otherworldly feel to it. It’s also a wonderful place to kick back and take in (another) view of the beguiling Chicago cityscape.

Discover Boystown

Boystown, Chicago’s gay village, is something special. About a 20-minute drive from downtown, it’s the heart of the LGBTI community in Chi-Town, and the best place to stake out a viewing spot for Chicago Pride in late June.

While there are a plethora of bars and restaurants on and surrounding Halstead Street, the heart’s heart is undoubtedly the Center on Halstead. It’s the largest queer community center in the Midwest, and the perfect place from which to embark on the Legacy Project tour.

The project is so simple, yet so effective, that you wonder why more cities don’t have one.

A succession of beacons (that look a little like gay spaceships) have been placed along Halstead. Each beacon tells the story of a pair of LGBTI lives.

The people honoured aren’t limited to Chicagoans, nor to Americans. The late British codebreaker Alan Turing has a space. And another name who deserves a mention here is Fr. Mychal Judge.

Judge, a gay Franciscan friar, was the beloved chaplain to the New York Fire Department. He entered the North Tower during the 9/11 attacks, saying he needed to be with his men, and was killed by falling debris, giving the Last Rites to an injured firefighter. He was recorded as victim 0001.

You might argue that his name would be famed in the annals of history. But, due to his sexuality, this writer suspects this brother has been less honored than he might otherwise have been.

Victor Salvo, the project’s executive director, leads group tours of the beacons, going into greater detail about the lives of those featured than the plaques can.

Photo courtesy of Illinois Office of Tourism

Photo credit: Illinois Office of Tourism

The tours are private, so you can pair it with a dinner, wine tasting or, a bar crawl, which is a great way to get to know the local watering holes. But, given America’s liberal free-pour measures, how much you’ll remember is questionable.

If you want dancing, Boystown’s a great place to do it. Similarly, if you want to sit and rack up the free-pours, it’s a great place to do that too.

Sidetrack, situated on Halstead, is a great place to do both. A warren of rooms, it caters for every taste and is the perfect place to start your night. It does a selection of alcoholic slushies that are the dream, though we suspect there’s more sugar in them than in one of Tate & Lyle’s factories. But it doesn’t count if you’re on holiday, right?

For more information about queer nightlife in the city, including the equally buzzing gayborhood Andersonville, read our guide here.

For foodies

This writer thinks America does the best food in the world.

Forget the stereotype of piles of fried food that no one could possibly finish. (Though there’s a place for that). The USA does quality cuisine with a flair I’ve found in few other places. And Chicago’s food scene is right up there with the best of them.

You can’t not indulge in a deep-dish pizza. It’d be like forgoing cheesecake in NYC. Or remaining cheese-free in France.

We went to Giordano’s, and it was beyond satisfying. To call their wares pizzas is to undersell them entirely. They’re pies masquerading as pizzas.

The individual is more than enough for one. You may not eat again for the rest of your trip, and what we ate has may have shortened our life by about five years. But it was totally worth it.

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For something a little less carbicidal, head to GT Fish and Oyster where our nautical friends have been transformed into some truly scrumptious dishes.

The halibut and fish tacos are to die for. You might argue nothing beats a Brighton chippy for fish and chips, this place will leave you questioning just how true that statement is.

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Much like Vanessa Williams, we’ve saved the best for last. If you eat nowhere else in Chicago, you must – repeat must – go to STK. Think steakhouse meets statement dining. Basically, the steak is so epic, people dress up for it. It offers an array of Americana-infused dishes but with best ingredients available.

Order everything. Twice. If, however, your budget can’t stretch to that, then you must have one of the flawless steaks or a succulent chicken dish. Fill your plate up with the creamy potatoes and Brussels sprouts (this writer is constantly amazed at the American ability to turn such a disappointing vegetable into absolutely delicious dishes) and gorge to your heart’s content. Also, finish up with the baked cookie. Thank us later.

Where to stay

We spent the trip based at the hiptastic ACME Hotel Company, an achingly stylish three star located in the arty River North district. To read our full review of the hotel, click here.

For more information about Chicago, head to and also You can also visit dedicated travel agents like Jack Leaf at Destiny Travel via the official website or [email protected].