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As the late, great Frank Sinatra once said, “Chicago is my kind of city. With architectural gems, multidisciplinary art, live music, raucous bars, loyal sports fans and Michelin-caliber dining, all in a dynamic landscape of culturally unique areas, isn’t it for everyone? Here, you’ll find the best of a waterfront city with skyscrapers (once the tallest in the world!), thriving creative communities in the suburbs, and the buzz and fun of the warmer months—especially this weekend during Lollapalooza. .
Although social media might suggest otherwise, the city is known for more than selfies on The Bean (er, Cloud Gate) and deep-dish pizza, though the latter is definitely on this list.. Its world-class attractions and historical treasures ensure that there truly is something for everyone, and the list of things to do is impossible to tackle in just one visit. Think: quirky antique shops, late-night jazz sets in iconic locations, creative fine dining and off-the-beaten-track hideaways, all sprinkled with Midwestern hospitality. Here’s how to explore the Windy City, where, despite its nickname, the locals are second to none.
Art Institute of Chicago
Known for its sprawling campus and sun-drenched galleries filled with modern and contemporary masterpieces, the Art Institute of Chicago in Grant Park dates back to 1879 as one of the world’s oldest and largest art museums. The permanent collections are unique, but the institution’s heavy rotation of exhibits makes it worth the visit. Now open, “Life and Afterlife in Ancient Egypt” and a fascinating retrospective on French painter Paul Cézanne are two pop-up exhibitions that are absolutely must-sees.
Green Mill Cocktail Lounge
No visit to Chicago is complete without enjoying some jazz. Located in Chicago’s Uptown neighborhood, the iconic century-old Green Mill plays live music seven days a week, with Thursday nights specifically dedicated to dance and poetry slams on the third Sunday of the month. This famous, cash-only hangout was home to mobster Al Capone, who frequented the contractor during Prohibition. Fans 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 covered in gold rotundas, lakes and more before arriving at the impressive glass greenhouses that make up the Garfield Park Conservatory. Pass the mature gardens and wander between rooms open to palms, ferns, desert cacti, delicate flowers and exotic plants (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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Rose Mary
High boss Winner and South Side native Joe Flamm brings Italian-Croatian flavors to the West Loop Fulton Market District with his first restaurant, Rose Mary. The bustling concept features Flam’s creation of “Adriatic drink cuisine,” packed with bold flavors and serving modern dishes on thoughtful courses. The open kitchen gives diners a glimpse of all the action, and between the sous chefs, you’ll sometimes see Chef Joe himself calling the shots. As the menu changes seasonally, the Stracciatella starter is a must, and you can’t go wrong with the Malfaldine or the pork rib pampanella.
Clause
Lincoln Park’s crown jewel, Alina, is undisputedly sophisticated molecular gastronomy led by creative chef Grant Achats, who has won three Michelin stars and awards. Enter through an unmarked door and enjoy a multi-course tasting menu with mind-blowing creations such as a single black truffle explosion or a complex array of flavors dressed with surgical precision and a sweet finish. Paint directly on your dining table. The Alinea experience is full of aromatic vapors, tricks and tableside theatrics, so you’ll have a lot of fun this time.
Pequod Pizza
If you want the ultimate Chi-Town deep-dish experience, Pequod rules the roost. It’s been an institution since the 70’s and is a favorite among locals for traditional pan pizza (which they try to keep a secret from out-of-towners). The crunchy, caramelized crust that sets Pecode apart from other deep-dish joints is what some say is an age-old experience, making it the best pizza in Chicago, if not one of the best in the country. (Sorry, New York.)
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Palmer House
Where better to enjoy a martini than under 24 carat gold Tiffany and candelabras and Greek frescoes by French painter Louis Pierre Regal? Palmer House is richly defined – steeped in history and the enduring love stories that drive its origins. Enter the lobby through the travertine double staircase and you are immediately transported to another universe. The French-inspired aesthetic can trace its roots back to Bertha Palmer, the lucky dame who was given the hotel as an extravagant wedding gift by her husband, Potter Palmer. After meeting Claude Monet, she began amassing an impressive collection of Impressionist art (now on display at the Art Institute), which stands as the largest collection outside of France. Enjoy a cocktail at the Palmer Lockwood Lobby Bar before starting your evening. Tip: Live entertainment is offered on weekends.
Three dots and a dash
At the secret alley entrance, Three Point and Dash is a spectacular view over the island bar with amazing craft cocktails and tropical elixirs. Choose your poison by flavor, by a clever name, or by the grotesque cup it’s held in. For rum connoisseurs, the bamboo room inside offers a curated experience with daiquiris, interpretations of classics and progressive cocktails made using modern techniques.
Beach roof
This sprawling rooftop at the top of a navy ship has the best perch in the city, with expansive views of Lake Michigan and the coastal skyline. The bright and airy space is open year-round, with fireplaces, play areas and comfortable seating perfect for group hangouts and gatherings for days and nights. And, if you’re new to Chicago, it’s the perfect place to stop after visiting Grant Park and the Pier.
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Chicago Athletic Association
Once an upscale private club, this downtown boutique hotel is a classic stay that boasts a Venetian Gothic exterior, a historic lobby, and custom vintage-inspired furnishings like iron bed frames and pommel horse chairs. Popular with travelers and locals alike, it features an indoor bocce and game room foosball, a clubby Cherry Circle Room restaurant, a chic speakeasy-style microbar milk room with a neighborhood favorite bartender, and rooftop bar Cindy with great views of Millennium Park.
Robey
Centered in Chicago’s hip Wicker Park neighborhood, known for its creative spaces, wine bar and cozy cafes, The Robey is a minimalist, mid-century Art Deco, triangular building at the intersection of Damen and Milwaukee. and North Streets. The eclectic rooms range from suites to lofts, perfect for group travel. Sip a cocktail at the rooftop Cabana Club, where you’re more likely to mingle with locals than visitors, or soak in the hot tub, then take in the metropolitan view of downtown Chi.
Waldorf Astoria Chicago
Inspired by a Parisian château, Chicago’s stylish Waldorf Astoria is located in the Gold Coast neighborhood, steps away from the shopping of Michigan Avenue. The cobblestone motor court sets the tone for the estate’s sophistication and grandeur, endorsed by Coco Chanel. Inside, crystal chandeliers, plush velvet furniture and gleaming marble work with large rooms and suites. And, for the ultimate break from the hustle and bustle of the city, step into the spa for a massage or detox in the eucalyptus steam room. Fun at it’s best.
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Essential component Exfoliator
Wash away all that city humidity and you’ll be cleansed with this super-fine exfoliator.
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For city days, nights, and in general, you need a little bit of these three shades to keep your lips happy.
Clé de Peau Beauty Enhancing Liquid Eyeliner
There’s nothing like a good eyeliner, and with two precision pens you can achieve the perfect sharp wing.
QMS Advanced Eye Care Day and Night Eye Cream
Save luggage space (and under your eyes) with this two-in-one day and night cream.
Taylor Stoddard is a freelance journalist covering everything from travel to fashion to lifestyle. When she’s not writing, she might be trying out a new restaurant, reading the latest NASA headlines, or trying to learn a new language at 35,000 feet.
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