Chicago travel inspiration: discover America’s capital of cool at the newest Hoxton Hotel

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Hannah Keegan
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Hoxton Chicago

Stylist features writer Hannah Keegan discovers sultry jazz clubs and hip hotels in one of America’s happiest cities. 

I’d never been told that upon entering a bar I’d have to take a vow of silence. Have you ever heard of such a thing? I was a little indignant; it was a bar, not a temple. But the doorman was very insistent. “Absolutely not a word, little lady.”

I sighed. I complied. And, I thought, I’ve never been to Chicago, where they are near-religious about jazz. It’s my second night in the city and I’m at The Green Mill, a dimly lit jazz haunt that Billie Holiday and Frank Sinatra once frequented. 

Al Capone loved it here, too. His favourite booth was slap-bang in the middle, so he had clear views of every entrance in case the cops showed up. If that happened, he could disappear into the club’s secret tunnel leading directly to the club he owned across the street. Tonight, people are huddled in red-velvet booths happily – and silently – sipping negronis as they listen to the melodies. It takes about half a second for me to be happy about it, too. 

The hotel's bars are the definition of downtown cool.
The Hoxton hotel's bars are the definition of downtown cool.

I’m here because of The Hoxton. In April, the London-born hotel group known for its lobby culture opened its third North American location, after Williamsburg and Portland last year. This time, the group has picked the trendy Fulton Market district, also home to Soho House, to set up shop. 

The area’s known for its coffee shops and ramen houses, with Downtown Chicago – home to Grant Park, Anish Kapoor’s Cloud Gate sculpture and the Museum of Contemporary Art (where Virgil Abloh held his Figures Of Speech exhibition over the summer) – a 15-minute train ride away. America’s ‘second city’ is a thriving metropolis of history, food and culture, with a global survey last year finding its residents to be the happiest of all 32 cities surveyed. 

Mid-century styled bedrooms will appeal to design fans.
The Hoxton's mid-century styled bedrooms will appeal to design fans.

The hotel itself is the expected mix of dark wood, muted tones and lively atmosphere. There are 182 rooms in signature snug, cosy and roomy categories, and it’s the group’s first location with a rooftop pool, surrounded by fire pits and seating for every season.

And then there are the restaurants. This is the Hoxton hotel for foodies. There are two: Cira, which is Mediterranean-inspired, offering grilled octopus, marinated beets and falafel. And Cabra Cevicheria, led by chef Stephanie Izard (fan favourite on Bravo’s Top Chef show and kind of a big deal here), offers relaxed Peruvian dining. If you want to branch out, Izard’s James Beard award-nominated restaurant Girl & The Goat is just around the corner. Alternatively, head to Split Rail for Southern fried chicken, biscuits and gravy or Hoosier Mama bakery for the best pies in town. 

With two restaurants, The Hoxton is a hotel for foodies.
With two restaurants, The Hoxton is a hotel for foodies.

To my own surprise, the highlight of my time in Chicago was a comedy show at club The Second City. She The People is a feminist improv show that dives into the woes of being a woman in America – and it will leave you with a jaw ache from laughter. On uteruses? “If I wanted the government up in here, I’d fuck a congressman.” On anti-vaxxers? “I’m going to use apple cider vinegar and a vision board.” It’s little surprise this place birthed the likes of Amy Poehler, Tina Fey and The Late Show host Stephen Colbert.

Joking aside, my parting advice is this: just don’t leave without taking in some jazz. And don’t expect anyone to laugh if you talk during it. 

Rooms at The Hoxton start from £99 per night; fly from London Heathrow to Chicago with United Airlines from £336.

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