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Why Chicago is overtaking its coastal cousins to become the US’s most amazing gay destination

Why Chicago is overtaking its coastal cousins to become the US’s most amazing gay destination

The incredible Chi-town skyline boasts 116 skyscrapers...

‘Remember to breathe,’ I tell myself, as the helicopter pilot’s voice rings through my ears, my body judders and 1,172 glittering high rise buildings unfold before me.

The Chicago Helicopter Experience is shredding my nerves, but it’s also highlighting just how magnificent this 2.7 million-person city truly is.

Grandiose skyscrapers pierce a skyline at once jagged and curiously neat – a result of meticulous urban planning after the Great Chicago Fire of 1871. Behind me, the staggering Lake Michigan disappears into the night like an ocean.

The Chicago Helicopter Experience (credit:

Like the lake, the city – Obama’s hometown – is huge; the largest in Illinois. The state capital of Springfield – the former hometown of Abraham Lincoln – is a three-hour drive away, and home to just 117,000.

The view is exhilarating, expansive, absurd, and in my book, about as glamorously cosmopolitan as America gets.

Chicago’s skyline by nightfall (credit: Pixabay)

The Windy City

Which instinctively – and somewhat guiltily – makes me draw comparisons to the only other US city to make me feel this way. And it’s some 790 miles east of here.

Indeed, the mighty New York City is home to five of the US’s tallest buildings, including the tallest, One World Trade Center (1,776 ft). It and Chicago’s skylines seem almost connected.

Chicago’s skyline (credit:

Chi-town trails just behind with four – its tallest, Willis Tower, is 442.1m [above]. What’s more, it boasts the Skydeck Chicago observation point, which offers unobstructed and roundly terrifying views of the city through a glass platform (accessible with the money-saving Go Chicago Card).

Chicago does, however, hold the distinction of being the birthplace of the skyscraper. The Home Insurance Building – built in 1885 and standing at a now-miniscule 55m tall before demolishment in 1931 – was the world’s first. (For an informative tour of the city’s existing buildings, try the Architecture Foundation Tour, also accessible with the Go card).

Chicago Lakefront Trail (credit:

But this, for me, is where the rivalry ends. If anything, NYC and Chicago feel like brother cities.

In my (admittedly strange) imagination, the former is the fashionable, cutting-edge and completely overexcited younger brother, cheekily stealing the limelight from its equally handsome, irresistibly self-assured older brother. The two stand shoulder-to-shoulder, and both have equally sprawling LGBTI communities.

The Bean (credit:

Photos with The Bean and a T-rex called Sue

Chicago gives any world city a run for its money with its staggering art and culture scene.

It’s symbolised by The Bean – Anish Kapoor’s inexplicably fascinating public sculpture known officially as Cloud Gate. It’s found in the well-manicured, picture-perfect Millennium Park [below]. (For the best selfie conditions go at sunrise when the light is forgiving and the crowds absent).

Millennium Park (credit:

Meanwhile, the Art Institute of Chicago is a stunning behemoth and mecca for art lovers.

Housed within its authoritative, front-facing neoclassical facade are 273 galleries and iconic works by Andy Warhol and Henri Matisse plus Roy Lichtenstein. In fact, every iconic artist you could think of…

Art Institute of Chicago (credit: Wiki)

From Grant Wood’s playfully stoic American Gothic to the second version of Vincent van Gogh’s timeless Bedroom in Arles series, these are paintings you need to see.

Likewise, I was blown away by Edward Hopper’s seductive, inscrutable Nighthawks. It’s one of America’s most famous works of modern art, and additionally, one of my favorite pieces ever.

Nighthawks by Edward Hopper (credit: Wiki)

Furthermore, the perfect compliment to the Institute is The Field Museum of Natural History, a 38-minute walk down the Lakefront Trail.

Here you’ll find another unforgettable Chicago icon, Sue: the largest and most complete Tyrannosaurus rex fossil ever discovered, on permanent display in the Main Hall.

Sue (credit: Wiki)

We stared at her for 45 minutes. Plus another 20 staring at Carl Akeley’s taxidermy The Fighting African Elephants.

We then tried and failed to see the other countless artefacts, exhibits and ticketed shows in under half an hour.

Boystown (credit: Adam Alexander Photography/

The boys of Boystown

My earlier metaphor about Chicago and NYC being brothers resonated (a bit) with some of the local guys I met. Mostly in the fantastically-named gayborhood Boystown, the first officially-recognized gay village in the States. 

Over beers at the city’s premier, multi-level gay bar Sidetrack one cute, adopted Chicagoan told me: ‘The fashiony gays migrate to New York. The showbiz gays migrate to LA. The down-to-earth gays head here.’

Kit Kat Lounge (credit: Adam Alexander Photography)

As a serial traveler, I’ve socialised, or attempted to socialise, with queer strangers in the aforementioned cities with mixed success. (For me, the guys were coldest in Miami). But in Chicago, everyone was super-friendly. Whether sipping elaborate cocktails in the moody, trendy Kit Kat Lounge and Supper Club, or immersed in the shabby chic Chinese stylings of tucked-away watering hole Wang’s (another great name), there’s no pretension.

Boystown is teeming with queer bars and clubs, with many dotted along the bustling Halsted Street; also the base for the city’s Pride festivities each June. For other drinking options try the hipster dive bars of Logan Square, or perhaps one of the many jazz clubs throughout the city.

One of the hotel’s London-inspired suites (credit: Virgin Hotel Chicago)

Blockbuster hotels, both classic and cutting-edge

Fresh, funky stopover, the four star Virgin Hotel Chicago has you covered. The box fresh, 250-room hotel opened in 2013; the first in Virgin’s portfolio. Like on its airlines, service is upbeat and friendly. There’s a vividness and a sense of fun to the staff and the surroundings that make you feel excited to be here.

Playful touches of the brand’s native British eccentricity abound (see the Tube-inspired rug in one of the airy rooms, above). Crossing the Atlantic for a home-from-home was (for this London-based writer) comforting, and furthermore, disorientating!

The Commons Club (credit: Virgin Hotel Chicago)

Second only to the helicopter experience, the most glam moment of my trip was sipping daiquiris in the hotel’s Commons Club bar. Guests drink free from 7-8pm each night, a simple but effective gesture that should be prerequisite at every hotel (along with free wifi, which this has).

The hotel’s grand lobby (credit: Palmer House Hilton Hotel)

Then, for a more classic hoteling experience full of throwback glamor, head to another four star, the 1639-room Palmer House Hilton Hotel. It’s the oldest continually-operated hotel in Chicago, having welcomed its first guests in 1873 (its grand opening a few years before was thwarted by the Great Fire).

It’s famed for its striking lobby mural, resplendent suites, lavish indoor pool and the fact that the chocolate brownie was invented here

A typical suite in the hotel (credit: Palmer House Hilton Hotel)

It’s also excellently-located downtown in the heart of the Loop district. What’s more, The Bean is just a seven-minute walk away. (So, of course, popping out for your early morning selfie is pretty painless).

The two best eats

Gino’s Deep Dish pizza is a Chicagoan institution (credit:

First stop: Gino’s East, for an essential Chicago-style deep dish pizza. More akin to a dense, baked pie than anything that’s emanated from Naples. I could barely manage two slices of my piping hot, pepperoni-peppered concoction, which is cooked for an hour. Moreover, you could live on one of these for a week. The 50-year-old establishment, with its revealing graffiti-covered walls which you can add to, is a quintessential Chicagoan experience.

Finally, I loved the farm-to-table dirty burgers at the hipstery Grange Hall Burger Bar. (‘The Ultimate’ is comprised of grass-fed beef, Muenster cheese, applewood bacon, rocket, onions plus horseradish aioli. Sorry for making you hungry). For the upmarket diner, Chicago also has 21 Michelin-starred restaurants to choose from.

The Bean (credit: Main picture of skyline by night credit: Wiki)

For more information about Chicago and Illinois, visit, home of the Illinois Office of Tourism.