NYC? You’ve done it! LA? Facelifts and fake smiles. San Francisco? That’s a long way to go for an old prison and earthquakes (jokes – we love SF!) But there’s a gem of a holiday destination nestled in America’s Midwest that any self-respecting gayer seriously needs to see…

Until recently, Chicago hasn’t had the glamorous PR afforded to certain other American metropolises. A city known largely to Brits thanks to supermarket pizza and a load of bob-haired actresses trotting around the West End in flapper beads and fishnets. But the last few years have seen a huge upswing in the popularity of The Windy City and we can see why.

A city that taught us how to sing (the blues) and how to dance (the infamous 80s house movement), there was an inkling of what to expect from the people of Chicago before we’d even touched down on US soil. Two fabulous air stewards, Midwest born and raised, were soon falling over themselves to tell us the best gay bars to see during our stay. These jovial ladies knew what this group of homo-leaning Brits abroad wanted – strong drinks and sights too big to fit into our tiny island.


For us, there’s nothing better that driving into a big city from the airport and watching the skyline appear, seeing both iconic and alien architecture gradually arriving into view. Chicago delivers on this big time; a city that built ever upwards from the Great Chicago Fire of 1871 and never looked back. Or down. An impressive mixture of classic, heavy US architecture known as ‘Chicago School’ (yeah, they kind of invented it) and ultra modern, glass sky botherers. To really learn about the city, the Architecture River Cruise is highly recommended. Don’t let its slightly school trip-style name put you off, it provides a fascinating insight into a city with a relatively short but intriguing history. A city that seemingly learns from its mistakes and uses it to build a better, more prosperous place for its citizens.

When you’ve stayed at (read: woke up in) a lot of hotels, you know what to spot in well-run accommodation. If you’re looking for a slick, modern hotel which feels like your own apartment (only nicer) then the Dana Hotel and Spa is for you. Warm, contemporary and gorgeous in both energy and décor, with friendly staff you can have a bit of banter with, rather than the grinning drones America’s service industry loves to foist upon tourists. It’s reasonably priced and boasts a killer rooftop bar, too. Shout out to the girls from the gorgeous Dana Spa who massaged out months of tension from my shoulders and at least a year off my face!

Dana is just a short walk from the Magnificent Mile, a section of Michigan Avenue chock full of mid-range to high end stores, a number of landmarks, restaurants, theatres, museums, bars and media. History, communication and the almighty dollar collide here for an experience that’s genuinely more sophisticated and visually stunning than the tourist fodder many cities serve up. But it’s an area naturally for visitors and affluent residents, not so satisfying if you like your holiday menu to have a taste of what life’s really like for your destination’s citizens.

If you want to get under the city’s skin, and increase your chance of running into a buff slab of preppy man candy, rather than an excitable mother/daughter combo laden with shopping bags and hair extensions, then onward to Boystown. Famously the world’s first gaybourhood, the area has an extra buzz about it. Anywhere with an eclectic mix of cultures, communities and household incomes commingling together ideally breeds creativity and a sense of togetherness. Lakeview’s Boystown wins here with scores of independent shops, boutiques and speciality restaurants (in particular, Yoshi’s Cafe, a family run French-Asian fusion, and Wood, a homo hotspot for food and cocktails).


Sitting alongside this cultural melee are the Archdiocesan Gay and Lesbian Outreach, one of the few LGBT-specific churches, rainbow pylons featuring plaques dedicated to important figures in queer history and the community’s crowning achievement, the Center on Halstead. This is the largest LGBTQ community centre in the Midwest with more than 1,000 people walking through its doors every day. Offering sexual health services, therapy, training, events and programs, it’s truly inspirational and something the UK should be taking notes from.

For a similar, diverse vibe, check out the Swedish-inspired Andersonville, another centre of homoxualiciousness (yes, we made that word up), home to the Gerber/Hart Library, the largest gay and lesbian archive in the Midwest and the gorgeous Hollywood Beach, ridiculously popular in the summer.

Art, culture and beauty thrive in Chicago and are readily available to the public. There’s a huge artist community, particularly around River North, which, after Manhattan, hosts the largest number of galleries in the US. Every form and style imaginable sit side-by-side in a bustling hive of coffee shops, eateries and bars; a perfect way to spend a sunny Saturday afternoon.

Millennium Park proudly boasts award-winning credentials as a centre of leisure, and you can see why. The park is exquisite, particularly the architecturally stunning Jay Pritzker Pavilion, a sophisticated outdoor concert venue, and, of course, Anish Kapoor’s hugely popular Cloud Gate sculpture, more commonly known as The Bean. Even if you’re one of those miserable buggers that has no time for what traditionally passes for art or culture, and sometimes even we’re guilty of that, you just can’t ignore jaw-dropping beauty of The Bean. A smooth, ultra modern, stainless steel structure that distorts reality in its reflective surface and contrasts beautifully with some of the more hulking architecture Chicago serves up.


Chicago is certainly a town that loves to drink, and does so with an array of high end bars that allows you to take in the night skyline with a cocktail, right through to friendly dive bars where you can watch sports, drink cheap beer or even soak up some jazz. Chicago’s approach to boozing is refreshingly fun and light-hearted (Check out the awesome cocktail bar Three Dots and a Dash) in comparison to London’s less than charming alcoholism, where vomiting in the gutter deftly masks the fact you’re a highly uninteresting person. Even in the most lowbrow of boozers and restaurants, Chicago musters up an atmospheric, quirky charm.

If you don’t just want to get sloshed and are looking for some good eats, Chi-town is full-to-bursting with them! We highly recommend having a delicious breakfast at Beatrix, lunch at the well-heeled Siena Tavern and dinner at the ultra-funky Graham Elliot Bistro. These barely even scratch the surface of all the delicious dining options on offer around this town, but we don’t have an extra eight pages to go through them all.

Quite honestly, we didn’t want to leave Chicago. This delicious melting pot of a city has now becoming a major player in international business and tourism while retaining the feeling of a warm and welcoming large town. Chicago – we’re in love! n

GT stayed at the Dana Hotel,

GT travelled with United Airlines, Discover more at

Words Lee Dalloway



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