Condé Nast Traveler 

From world-class museums and award-winning food and drink to a thriving live music scene, soaring architecture, and miles of waterways and green space, Chicago is a veritable playground to the culturalist. With so much to see and do, planning an itinerary can overwhelm tourists and longtime residents alike. These 10 unique experiences traversing art, music, architecture, film, and food and drink will give you a deeper look at Chicago’s local art and culture scene and make you fall in love with the city—if not for the first time, then all over again.

Chicago Friday Night Flights
With more than 60 breweries and counting—another may well have opened while we typed this sentence—Chicago has established itself as a leader of the nation’s meteoric craft beer movement. Chicago Friday Night Flights, produced by the Illinois Craft Brewers Guild in partnership with Choose Chicago, tours the city and its breweries by neighborhood, bringing local brewers together throughout the summer for an evening of beer and bites. Taste the libations from Pullman, Bridgeport, and Pilsen, or drink up in the city’s newest urban recreation waterfront via the Riverwalk event. Warning: Tasting events sell out fast, so plan accordingly.

Chosen Few Picnic & Festival
Feel the energy of house music in the city where it was born. Now in its 28th year, the Chosen Few Picnic & Festival evolved from a small gathering of friends behind Chicago’s Museum of Science & Industry in 1990 into one of the world’s longest-running events dedicated to house music with upwards of 35,000 attendees. On July 7, in sprawling Jackson Park, the Chosen Few DJs—including originals Wayne Williams, Jesse Saunders, Alan King, Tony Hatchett, and Andre Hatchett—will preside over 12 hours of soulful dance music, fun, and of course food in the form of abundant picnic spreads. This is, after all, a massive Chicago family reunion.

Millennium Park Music & Film Series
Nothing says Americana summer like live music under the stars—which is partly why Millennium Park’s (free!) Summer Music Series remains a favorite among locals. From mid-June through mid-August, Jay Pritzker Pavilion hosts free performances spanning jazz, indie rock, and vintage reggae. Unfurl your picnic blanket beneath Frank Gehry’s captivating steel trellis, crack open a Goose Island ale (one of a few drink options available for purchase), and soak in the best of the fleeting Chicago summer. More of a movie buff? Each Tuesday from June 5 to Aug. 21, come see your favorite films on a 40-ft. LED screen at Jay Pritzker Pavilion and on the Great Lawn. Before each feature the ChicagoMade Shorts program will screen an original work by a local filmmaker. Or get out and see Chicago’s other beautiful parks with 200-plus screenings showing citywide through the Chicago Park District’s 17th annual Movies in the Parks.

Chicago Gourmet
Gearing up for its eleventh year this September, Bon Appétit presents Chicago Gourmet continues to grow alongside the public’s swelling appetite. Kicking off Sept. 28 with the Hamburger Hop®, a delicious showdown to determine the city’s best burger, the event boasts three jam-packed days of celebrity chef–led cooking demos on two stages, wine and mixology seminars serving up the coolest trends in a glass, and an unmatched lineup of tastings featuring hundreds of renowned brewers, vintners, and spirits makers plus 250 of Chicago’s best chefs and restaurants—at beautiful Millennium Park. Tickets go fast; get yours and bring your appetite.

Art Design Chicago
Appreciate Chicago’s singular art and design fingerprint through this citywide initiative. Spearheaded and funded by the Terra Foundation for American Art, Art Design Chicago reveals little-known narratives of ingenuity and perseverance and provides new insights on Chicago’s enduring influence on fine and decorative arts, graphic and commercial design, product development, and film. Among the more than 30 exhibitions taking place throughout the year are Arte Diseño Xicágo, a look at the Mexican experience from the World’s Columbian Exposition up to the Civil Rights Era, at Pilsen’s National Museum of Mexican Art (through August 19), and a retrospective of preeminent Black Renaissance artist Charles White (June 8 through September 3 at the Art Institute of Chicago).

Bobby’s Bike Hike
Make the most of Chicago’s increasingly bike-friendly status with an easygoing cycle tour from Bobby’s Bike Hike, the city’s oldest bike tour operator. Experienced guides take riders of all ages and fitness levels along bike paths past sights spanning leafy historic neighborhoods, towering skyscrapers, sprawling parks, and bygone gangster haunts—offering a delightful mixture of knowledge and sass. Wide-ranging tours include “City Lights at Night Tour,” “Lakefront Neighborhoods Bike Tour,” and the “Bikes, Bites & Brews Tour,” which samples both stalwart and up-and-coming food and beer.

EXPO CHICAGO
Each September, this international exposition of modern and contemporary art kicks off the fall art season, playing host to preeminent international art galleries alongside one of the highest-quality platforms for global contemporary art and culture at historic Navy Pier. Provocative discussions and exhibits showcase what’s hot on the world art stage. This year’s edition aligns with Art Design Chicago to present various programs and events from performances to panel discussions to screening events throughout EXPO ART WEEK, September 24–30.

Open House Chicago
Ever wanted to sneak into a beautiful repurposed mansion, a historic music venue that’s closed for renovation, or an exclusive private club? For 48 hours each October, the Chicago Architecture Foundation validates these roguish impulses via Open House Chicago, a free public festival that grants behind-the-scenes access to some 200 buildings scattered across the city’s 77 neighborhoods. Get an inside look at such historic sites as a stunning Art Deco apartment in Hyde Park, a warehouse filled with movie props, and a former hotel from the 1893 World’s Columbian Exposition, featuring a vine-draped atrium. Keep an eye out for this year’s list of sites, coming in September.

John Singer Sargent and Chicago’s Gilded Age Exhibit at The Art Institute of Chicago
Famous turn-of-the-century portraitist John Singer Sargent lived much of his life abroad, but his lesser-known Chicago exhibitions left an indelible mark, helping elevate the city to become the recognized center for contemporary art it remains today. From July through September at the Regenstein Hall at The Art Institute of Chicago (where Sargent showed several times during his storied career), explore the artist’s creative accomplishments, relationships, and impact on Chicago through roughly 100 objects amassed from the museum collection, private collections, and public institutions. Beyond the man himself, you’ll delve into the Second City’s Gilded Age within the context of a modernizing international art scene at the turn of the 20th century.

Architectural Boat Tours
As the weather warms up, arguably the best way to take in Chicago’s towering architecture is by boat. From speedboat tours to a seasonal water taxi, you’ll find numerous options for doing some inspired floating on Chicago’s enchanting waterways. The Chicago Architecture Foundation River Cruise (colloquially known as Chicago’s First Lady Cruises) offers a terrific glimpse into the city’s riverfront via comprehensive 90-minute tours of more than 50 buildings. CAF-vetted docents guide you through the architectural styles that helped fill in the city’s skyline, and share the oft-colorful stories of the people who designed and built them. Did we mention that each floating vessel sports a full bar? First Lady Cruises depart from Riverside Gardens on the Riverwalk at Michigan Ave. and Wacker Dr. from late spring to late fall.