ELLE Escapes: Chicago

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Chicago is a great place to be year-round, but there’s something about a Chi-town summer. Maybe it’s the welcome respite from those frigid winter months. It also doesn’t hurt that there’s plenty to see and do now that the sky is clear and the sun is out. Want to spend the day at The Art Institute of Chicago? Or perhaps try some deep dish pizza at Pequod’s? If you plan to be in town this weekend, you may even venture out to Grant Park for Lollapalooza, where some of our favorite artists, like Megan Thee Stallion and SZA, will be hitting the stage. And to make sure your energy levels stay high in the heat between sets, the Liquid I.V. Hydration Haven is your one-stop shop.

So whether you’re traveling to the Windy City for art, food, or festivals, let this be your non-exhaustive guide for what to see, where to eat, and more in Chicago.

What to See

The Art Institute of Chicago

Known for its sprawling campus and sun-soaked galleries filled with modernist and contemporary masterpieces, the Art Institute of Chicago in Grant Park remains one of the oldest and largest art museums of the world, dating all the way back to 1879. The permanent collections are exceptional, but the Institute’s heavy rotation of stand-out exhibitions make it worth the visit. Open now, “My New Yorks,” a stunning retrospective of Georgia O’Keeffe’s depictions of New York cityscapes, is a must-see.

The Green Mill Cocktail Lounge

No visit to Chicago is complete without enjoying some jazz. Situated in Chicago’s Uptown neighborhood, the iconic century-old Green Mill plays host to live music seven days a week, with Thursday nights specifically dedicated to swing dancing, and the third Sunday of every month to poetry slams. This famed, cash-only entertainment venue was a local haunt to mobster Al Capone, who frequented the establishment during Prohibition. Patrons can still sit in his booth, which has a clear view of both exits (for obvious reasons).

Garfield Park Conservatory

Get lost among the Spanish Baroque-style structures capped with gold rotundas, lagoons, and more, before arriving at the stunning glass greenhouse that ensconces the Garfield Park Conservatory. Traverse through the manicured gardens and wander between themed rooms with spaces dedicated to palms, ferns, desert cacti, succulents, and exotic flora (why not?). Throughout the year, the Conservatory hosts special pop-up events like beer tastings, yoga, expert talks, and, yes, flower shows.

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Where to Eat

Rose Mary

Top Chef winner and South Side native, Joe Flamm brings Italian-Croatian flavor to the West Loop’s Fulton Market district with his debut restaurant, Rose Mary. The buzzy concept offers a modern take on rustic dishes, packed with bold flavors and thoughtful coursing, that encapsulates what Flamm has coined “Adriatic drinking food.” The open kitchen gives dining patrons a glimpse of all the action, and amid exacting sous chefs, you’ll sometimes see chef Joe himself calling the shots. While the menu changes seasonally, the Stracciatella starter is a must, and you can’t go wrong with the Malfaldine or Pork Ribs Pampanella.

Alinea

Lincoln Park’s crown jewel, Alinea is undisputed for its ingenious molecular gastronomy, led by creative chef Grant Achatz, who has earned the eatery three Michelin stars and a bevy of awards. Enter through an unmarked door and enjoy a multi-course tasting menu with mind-blowing creations like a single-bite black truffle explosion or a complex take on surf and turf with nuanced flavors plated with surgical precision, and a dessert finale that looks like a literal splatter paint right on your dining table. The Alinea experience comes complete with scented vapors, tricks, and tableside theatrics, so you’ll be plenty entertained throughout.

Pequod’s Pizza

If you want the ultimate deep dish experience, Pequod’s reigns supreme. It’s been an institution since the ’70s and an undisputed choice amongst locals for traditional pan pizza (hold for those that will try to keep this a secret from out-of-towners). What sets Pequod’s apart from other deep dish joints is the crunchy, caramelized crust that some will say is a transcendent experience, making it the best pizza in Chicago, if not one of the best in the country. (Sorry, New York.)

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Where to Drink

The Palmer House

Where better to enjoy a martini than under 24-karat gold Tiffany & Co. candelabras and Grecian frescos by French painter Louis Pierre Rigal? The Palmer House is opulence defined—a hotel packed with history and enduring romantic myths that swirl its origins. Enter the lobby through the travertine double staircase and you’re immediately transported to another universe. The French-inspired aesthetic can trace its roots back to Bertha Palmer, the lucky dame who was gifted the hotel as an extravagant wedding gift by her husband, Potter Palmer. After befriending Claude Monet, she began amassing a remarkable amount of Impressionist art that stood as the largest collection outside of France (now on display at the Art Institute). Enjoy a cocktail at The Palmer’s Lockwood Lobby Bar before starting your evening. Pro tip: Live entertainment is offered on weekends.

Three Dots and a Dash

Tucked away in a secret alleyway entrance, Three Dots and a Dash is a whimsical take on an island bar, with exotic craft cocktails and tropical elixirs. Pick your poison by flavor, clever name, or the eccentric mug it’s housed in. For rum connoisseurs, the Bamboo Room inside offers a dedicated experience with a focused menu of daiquiris, renditions of classics, and progressive cocktails made using a modern technique.

Offshore Rooftop

This sprawling rooftop at the edge of Navy Pier has the best perch in town, with sweeping views of Lake Michigan and the coastal skyline. The bright and airy space is open year-round, with fire pits, game areas, and cozy seating ideal for group hangs and intimate get-togethers by day or night. And, if you’re new to Chicago, it’s the perfect place to stop after exploring Grant Park and the Pier.

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Where to Stay

The St. Regis Chicago

Right across the street from the famous Chicago River (which gets dyed green every year for St. Patrick’s Day), The St. Regis Chicago is in the center of all the action. Navy Pier, The Art Institute of Chicago, and Grant Park are all just a short stroll away. And if you want to stay in and take advantage of all that the hotel has to offer, there are options galore. Take your pick of evening champagne socials, luxury suites that come equipped with your own private butler, or the world-class spa that offers immersive experiences like meditation and sound baths.

Pendry Chicago

Located in Chicago’s iconic Loop, the Pendry Chicago is nestled near some of the city’s most iconic architectural hits. Both Millennium and Grant Park are just steps away, and the hotel is known for its commitment wellness rituals, including its partnership with AIRE Ancient Baths, which have steam rooms and treatments—perfect healing after Lollapalooza or the Chicago Marathon. The Pendry is also located in the 1920s-era Carbide & Carbon Building and carry the Art Deco style throughout, making it feel like you’re living in the world of The Great Gatsby.

Sofitel Chicago Magnificent Mile

Consider Magnificent Mile Chicago’s answer to New York City’s Fifth Avenue. Here, you’ll find luxury shops, five-star restaurants, and Sofitel Chicago Magnificent Mile. Infused with a contemporary French feel, the hotel offers a perfect blend of chic design and modern architecture. Even the lobby smells like you’ve stepped into a perfume ad. Indulge in in-room spa treatments from Windy City Massage for ultimate relaxation.

Off the Grid Travel Notebook

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Beauty Picks

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