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Weekend Travel Guide: Where to Stay, Eat, and Drink in Chicago

Here to make your visit to the Windy City a breeze.

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Defined by its rich history, culture, and legendary architecture, America's Second City has no shortage of unbeatable food and drink, unique attractions, and cosmopolitan magnetism—all with a touch of Midwest nice. It's easy to get to and easy enough to tackle in a long weekend. Plus, right now the weather is actually pleasant. To quote Kanye, who said it best, "If you don't know by now, I'm talkin' bout Chi-Town".

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Taking a seat in the skyline with @katiecassman_. #viceroychicago

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LUXE: The Langham

Cozied up along the Chicago River, The Langham's one-of-a-kind building, designed by architect Mies van de Rohe, is just one of the very stylish perks of this hotel. Visit The Langham Club, a private lounge on the hotel's top floor, for evening cocktails, canapés, and panoramic views of the city. For some R&R book a treatment at Chuan Spa where signature treatments are influenced by traditional Chinese medicine and the Wu Xing five elemental forces of wood, fire, earth, metal, and water.


TRENDY: The Viceroy

Situated in the heart of the Gold Coast neighborhood in downtown Chicago, with endless retail and restaurants within walking distance (hello, Barneys!), the new Viceroy boutique hotel is the perfect marriage of old-meets-new. Located in a 1920s-era building—formerly the Cedar Hotel—with complementary contemporary interiors, the Viceroy comes complete with awesome urban views, in-room spa services, and a rooftop bar and pool where you can sip cocktails while looking out over the Windy City skyline.


MODERN: The Kimpton Gray

Set in another Chicago landmark building in The Loop, The Gray masters a minimalist aesthetic with fun extras like a Tie Bar where you can rent a tie or pocket square for special occasions and a "Forgot It? We've Got It!" policy that will bring you left-behind essentials (like your Lululemons) upon request.


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There’s no better way to see Chicago’s famed architecture than by boat. Start the day with a Chicago Architecture River Cruise and sail past the must-see skyline built by the greats. For even more swoon-worthy design, head over to Chicago’s flagship Restoration Hardware store. Be prepared, this definitely isn't your run-of-the-mill furniture shop. The 70,000-square-foot store is located within the 3 Arts Club, a building dating back to 1914 where women once gathered to study the arts. Browse RH’s highly curated showroom, grab a bite in the courtyard café, relax at the rooftop garden, or kick back in leather club chairs while sipping wine in the vault.

FOR THE SPORTS FAN (but even if you aren't):

Root for the Northside’s home team (the Cubs, in case that wasn't clear) in the newly renovated Wrigleyville neighborhood, budding with hot new restaurants, boutique hotels (checkout Hotel Zachary), and quirky shops. Catch a game at Wrigley Field or hang back and grab a bite at one of the stadium’s nearby restaurants: Dutch and Doc’s for American fare and classic cocktails or Big Star for a fun-filled taco-, beer-, and bourbon-focused "honky-tonk."


There’s no shortage of museums in this sophisticated city. The Art Institute, The Field Museum, The Museum of Science and Industry, The Shed Aquarium…. But if it’s a beautiful day outdoors you may not want to be inside (Chicago winters are better for that). During warmer weather, we recommend taking a stroll through Millennium Park and capturing a highly Instagrammable bean selfie, or packing a picnic and catching a film or outdoor concert as a part of the park’s summer events series.

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To indulge in some iconic grab-and-go options, consider a hot dog at Portillos, a beef sandwich at Al’s Italian Beef, or a slice of deep dish at Lou Malnatis.


For a classic and slightly upscale meal, make a reservation at Somerset. The interiors, designed by award-winning design firm, Avroko, pay homage to the American country club. Order a half-dozen oysters to start and the whole roasted chicken for two.

Meat lovers should head over to The Publican. Its menu is farmhouse fare and its vibe, European beer halls. Order from a host of hearty dishes like spicy pork rinds and green chili sausage to share for the table, but don't discount the seafood and veggies, which are great for non-carnivores too. Wash it all down with a cider or craft beer from their highly curated selection.

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For delicious drinks and a buzzy atmosphere, head over to Cindy’s Rooftop at the Chicago Athletic Hotel. Enjoy one of their house-made craft cocktails like the Pea's Knees (made with mead, gin, créme de poire, sugarsnap pea, honey, and lavender) while sitting on one of the outdoor couches that overlook the city.


Before you visit this low-key speakeasy—complete with a discrete location and hidden door—in Chicago's Wicker Park neighborhood, make sure to read the "house rules" ahead of time (no cell phones, no Budweiser, no reservations). Order a Violet Hour classic like the Daisy 17, made with whiskey, lemon, grenadine, and orange bitters, and late night bites from their sustenance menu: Maybe the fried pickled chips and cheeseburger sliders to soak it all up?


For a unique cocktail experience, make a ressie at The Aviary in the West Loop—it's headed up by famed Chef Grant Achatz of The Alinea Group. These are not your run of the mill libations. Come prepared for smoking cocktails, whimsical presentations, and the faint feeling that you've just entered a very chic chemistry lab.

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