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The Cool Girl's Guide to Chicago

Who's ready for the Windy City?

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As one of our favorite Chicagoans, Ferris Bueller, put it, "Life moves pretty fast. If you don't stop to look around once in a while, you could miss it." The same could be said about his hometown, which has produced some of the country's biggest cultural achievements, like its urban blues, skyscrapers, and, of course, Kanye West. From Humboldt Park's recent surge of vintage shops to Wicker Park's mind-blowing culinary scene and Grant Park's 25 Years of Lollapalooza extravaganza this month, the lakefront metropolis has never felt so dynamic.

Where to Stay

  • Courtesy Londonhouse Chicago

    Londonhouse Chicago

    85 E. Upper Wacker Dr.; 312-357-1200;

    This 452-room skyscraper is a 93-year-old landmark with a just-completed 22-story tower attached.

  • Courtesy Kimpton Gray Hotel

    Kimpton Gray Hotel

    122 W. Monroe St.; 877-771-7031;

    The boutique chain’s fifth Chicago location is the iconic New York Life Insurance building in the Loop district.

  • Anthony Tahlier

    Virgin Hotel

    203 N. Wabash Ave.; 312-940-4400;

    Leave it to Virgin to add a sexy sheen to the art deco Old Dearborn Bank Building with the launch of its first-ever hotel.

  • Courtesy Chicago Athletic Hotel

    Chicago Athletic Association

    12 S. Michigan Ave.; 312-940-3552;

    Completed in 1893 by famed architect Henry Ives Cobbs, this former men’s club was gorgeously reincarnated as a four-star property in 2015.

Where to Eat

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    Doughnut Vault

    111 N. Canal St.; 312-285-2830;

    One heavenly bite of a buttermilk old-fashioned or triple chocolate from Brendan Sodikoff’s famous brick-walled shop and you’ll forget all about that pesky hour-long wait.

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    RM Champagne Salon

    116 N. Green St.; 312-243-1199;

    Enter through a cobblestoned back alleyway and settle in for a candlelit evening of steak frites and bubbly at this Parisian-style lounge from the restaurant group behind Old Town Social.

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    The Broken Shaker

    19 E. Ohio St.; 312-940-3699;

    Chicago is a serious cocktail town. And that’s exactly why Miami’s Freehand Hotel opened a follow-up outpost in River North. Choose from classic James Beard-nominated tropical libations and new Second City-inspired ones.

  • Pequod's Chicago Pizza/Facebook

    Pequod’s Pizza

    2207 N. Clybourn Ave.; 773-327-1512;

    Locals’ relationship with pizza runs, well, deep. One thing everyone can agree on? Pequod’s Chicago-style pies are the ideal balance of crispy crust and cheesy middle.

Where to Shop

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    3205 W. Armitage St.; 423-903-7093;

    Launched by Mary Eleanor Wallace (a nurse by day), this perennially cool Logan Square shop champions homegrown talent. Find Double Bonus necklaces, Nataliya Kotlova tunics, and an exclusive clothing collaboration with art brand BFGF.

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    15 E. Huron St.; 312-587-1000;

    Fifteen years after opening, Ikram and Josh Goldman's legendary luxury destination, with its glossy red façade and cutting-edge lineup of Céline, Delpozo, and Sacai, still takes our breath away.

  • moonvoyage/Instagram

    Moon Voyage

    2010 W. Pierce Ave.; 773-423-8853;

    Owner Susie Lee gives Wicker Park hipsters what they want: dreamy pieces (Bella Dahl dresses, Herbivore beauty products, Odette NYC jewelry) for less than the price of a four-day festival pass.

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    Madison Hall

    71 E. Madison St.; 312-683-9586;

    This hotel-lobby spot houses two posh boutiques: a unisex store carrying Aesop products and Moscot glasses, and a women's shop featuring Santa Maria Novella fragrances, Eddie Borgo rings, and fresh-cut flowers.

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    Space 519

    900 N. Michigan Ave.; Level 5, 312-751-1519;

    From $40 Wrigley Field prints by Rifle Paper Co. to $495 Rachel Comey jumpsuits, the offerings at this self-described general store (and sister to Madison Hall) include stylish pick-me-ups at every price.


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    Humboldt House

    1045 N. California Ave.; 312-785-1442;

    With its vibrant mix of kilim rugs, locally made ceramics, and modern wall hangings, this Humboldt Park outpost could easily be mistaken for a Venice Beach bungalow.

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    RH Chicago

    1300 N. Dearborn St.; 312-475-9116;

    You could spend a day exploring Restoration Hardware's new 70,000-square-foot flagship at Three Arts Club, which boasts a huge selection of rustic-sleek housewares, an elegant café, a rooftop park, and a performance space.

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    Modern Cooperative

    1215 W. 18th St.; 312-226-8525;

    If Sterling Cooper hired Jonathan Adler to decorate its offices, the result would be like this mod mecca brimming with vintage ('50s sofas, '60s bar carts) and contemporary pieces (cheeky pillows, typographical posters).

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    1657 N. Wells St.; 312-337-8000;

    A dizzying experience for any paper nerd, this Old Town trove stocks greeting cards, pens, and journals from indie presses like Ohh Deer and Elum, and a house line, which is sweetly called Civilettes.


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    Arch Apothecary

    1359 N. Wells St.; 312-291-9750;

    This bright shop is a go-to for luxury products from lines like Noodle & Boo, Oribe, and RGB Cosmetics. There's also a full menu of hair, makeup, eyebrow, and eyelash treatments.

What to Do

  • Clayton Hauck

    Longman & Eagle

    2657 N. Kedzie Ave.; 773-276-7110;

    A Michelin-starred restaurant, hopping bar, and upstairs lodging mean you’ll never have to leave.


  • Courtesy Volumes Bookcafe

    Volumes Bookcafe

    1474 N. Milwaukee Ave.; 773-697-8066;

    Happy hour just got a lot smarter thanks to this shop’s captivating reads and local craft beer.

  • Trustudio

    Heritage Bicycles

    2969 N. Lincoln Ave.; 773-245-3005;

    The chain’s general store serves up fresh java and custom bicycles (the first Chicago-made rides since Schwinn left in the ’80s).

  • asraigarden/Instagram

    Asrai Garden

    1935 W. North Ave.; 773-782-0680;

    The mash-up of enchanting greenery and twinkly accessories will make you feel as if you’re in an actual fairy tale.   


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