Fact: more songs were written about Chicago than about any other city in North America. It’s for a reason: the Windy City plays to its own beat, often ahead of everyone else. The proof is in the groundbreaking architecture and vibrant city life, but also in its enviable culinary and nightlife scene we just couldn’t wait to tap.
Stay
Soho House’s latest outpost is the mightiest of all, with a rooftop pool and its own boxing ring for your fighting pleasure. Located in the West Loop neighborhood, a haven for gourmands, the house number seven hits that right note between luxury and rustic chic. Think crystal chandeliers coupled with reclaimed wood and vintage furniture. Upon check-in, one is greeted with an artisanal cocktail, prepared in-suite. Take it straight to the clawfoot tub and make use of Soho House’s signature Cowshed bath products. If in need of even more pampering, visited the Cowshed Spa for a Skinny Cow Legs treatment to tune up your gams for all the sightseeing and shopping that needs to be done.
Eat
Steps away from Soho House are some of the city’s buzziest restaurants, including Publican and its lunch outpost/deli, Publican Quality Meats, where you can grab delicious, in-house prepared charcuterie or The Return of the Gyro, pork belly with raita and pea shoots on griddled flatbread.
Also in the hood is Au Cheval and its legendary meat escapades. Search hashtag #aucheval and you’ll find some of the richest foods on Instagram. It’s a meat fest, where double cheeseburgers (with bacon and fried eggs!) mingle with foie gras terrines and where hash is prepared with duck heart gravy. Yes, you want this.
Head over to the Wicker Park neighborhood to the ultimate hipster taco spot, Big Star. Yes, the tacos are delightful, but the atmosphere is what has diners flocking back: rock ‘n’ roll spun on vinyl, rock star-looking bartender prepping whiskey and tequila concoctions.
See
The best way to experience the city’s architectural greatness is by taking The Chicago Architecture Foundation River Cruise. This highly informative tour will walk you through the history of the city, from the location of the first skyscraper in America, to the many Mies van der Rohe masterpieces, to the building where Ferris Bueller’s dad worked — hey, also very important!
Anish Kapoor’s ‘Cloud Gate’ (nicknamed ‘The Bean’), located in Millennium Park, is the one Chicago selfie you’ll absolutely need to take (and also the one everyone will forgive you for). Art lovers will get lost at The Art Institute of Chicago, especially in the gorgeous modern wing, designed by starchitect Renzo Piano. On display: magnificent Impressionists, more Picasso than your mind could possibly process, and, in true Chicago style, countless modernists and minimalists, including late sculptors Donald Judd and Dan Flavin.
Shop
While Magnificent Mile has all the glory reminiscent of New York’s Fifth Avenue, we prefer a quainter Damen Avenue in Bucktown. You’ll find indie gems like Stitch, a lovely gift boutique carrying everything from furniture and textiles, to artisanal leather goods (keep an eye out for wicked leather totes by local fave, Munie) and jewellery. Down the street is Steven Alan, New York designer’s flagship carrying his own understated line in addition to the likes of Isabel Marant and Clare Vivier. Hold tight to your wallet at Helen Yi: you’ll find racks filled with Barbara Bui and Derek Lam irresistible.
Sip
One can’t skip the birthplace of Intelligentsia coffee, one of the leaders of the craft coffee revolution. Their creamy, fluffy espresso blend is something that can’t be missed, not to mention all the cool mags all the six locations carry (we’re partial to the Logan Square location).
On the boozy end, just east of Wicker Park, is Mott St. with some of the best cocktails in the Midwest. This modern Asian tapas bar plays with exotic ingredients for their innovative concoctions. Take, for example, Dashi Martini, a gin and sake blend topped with Dashi (soup stock) bitters. Sounds weird, tastes magnificent.
“Chicago, it’s a helluva town.”
