As the late, great Frank Sinatra once said, “Chicago is my kind of town.” With its vibrant mix of architectural gems, multidisciplinary art, live music, swanky bars, loyal sports fans, and Michelin-caliber dining, all within a dynamic landscape of culturally distinct neighborhoods, isn’t it kinda everybody’s? Here, you get the best of a bustling metropolis flecked with skyscrapers (that at one point were the tallest in the world!), nooks of burgeoning creative communities in suburban enclaves, and a buzzy, recreational riverfront that comes alive in the warmer months—especially during Lollapalooza in this weekend.
While social media might suggest otherwise, the city is known for so much more than selfies at The Bean (er, Cloud Gate) and deep-dish pizza, though the latter is definitely on this list. Its world-class attractions and historic treasures prove there is truly something for everyone, and the list of must-dos are simply impossible to tackle in just one visit. Think: quirky antique shops, night-long jazz sets in iconic venues, inventive fine dining, and off-the-beaten-path hideouts, all that with a sprinkle of Midwestern hospitality. Here’s how to navigate the Windy City that, despite its nickname, locals will attest is second to none.
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, “Life and Afterlife in Ancient Egypt” and a groundbreaking retrospective on French painter Paul Cezanne are two pop-up shows that are absolute must-sees.
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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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 Chi-town 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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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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Chicago Athletic Association
Once an elite private club, this downtown boutique hotel is a classic stay, boasting a Venetian Gothic exterior, historic lobby, and design-forward accommodations with custom vintage-inspired furnishings like iron bed frames and pommel horse benches. It’s beloved by travelers and locals alike for its indoor bocce and game room foosball, clubby Cherry Circle Room restaurant, elegant speakeasy-style microbar Milk Room with a neighborhood-favorite bartender, and rooftop bar Cindy’s, with the best views of Millennium Park.
The Robey
Centered in Chicago’s hip Wicker Park neighborhood, best known for its creative enclaves, vintage shopping, and cozy cafés, The Robey is minimalist and mid-century Art Deco in style, situated in a triangular building that towers over the intersection of Damen, Milwaukee, and North Avenues. The eclectic rooms range from suites to bunk lofts, optimal for group travel. Have a cocktail or take a dip in the hot tub at the rooftop Cabana Club where you’re more likely to mix with locals rather than visitors, then take in the metropolitan view of downtown Chi.
Waldorf Astoria Chicago
Evocative of a Parisian chateau, Chicago’s elegant Waldorf Astoria is nestled in the ritzy Gold Coast neighborhood just steps away from Michigan Avenue shopping. The cobblestone motor court sets the tone for the property’s sophistication and grandeur that would undoubtedly be Coco Chanel-approved. Inside, you’ll find crystal chandeliers, plush velvet furniture, and glossy marble fixtures with large rooms that might as well be suites. And, for the ultimate respite from city bustle, check in to the spa for a massage treatment or a detox in the eucalyptus steam room. Relaxation at its finest.
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Taylor Stoddard is a freelance journalist covering lifestyle topics from travel to fashion. When she’s not writing, she’s likely trying a new restaurant, reading up on the latest NASA headlines, or trying to learn a new language at 35,000 feet.