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Chicago City and Culture

Chicago Architecture
Chicago City and Culture
Stunning neighborhoods as distinct as sovereign nations, riveting art exhibits, and adorable boutiques that make you fantasize about opening your own: Chicago came to play! 
By Nicole Schnitzler, AFAR Local Expert
Photo by Richard Ellis/age fotostock
  • 1 / 10
    Chicago Architecture
    Chicago Architecture
    Many famous architects contributed to Chicago’s skyline, most notably Louis Sullivan with his elegant steel high-rises and Ludwig Mies van der Rohe with sleek black-and-glass skyscrapers. Don't miss the 110-story Willis Tower, now home to Skydeck Chicago and the Ledge, a series of transparent boxes that extend four feet from the building for bracing city views. These beauties and many more are best appreciated from an architecture cruise along the Chicago River via Chicago's First Lady Cruises—the only company to call upon expert docents from the Chicago Architecture Foundation for history and design insight. Chicagoland also has the nation’s largest concentration of houses conceptualized and built by Frank Lloyd Wright; visitors can tour his home and neighborhood in Oak Park, just outside city limits.
    Photo by Richard Ellis/age fotostock
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    Outdoor Festivals throughout the Year
    Outdoor Festivals throughout the Year
    Chicago’s best outdoor festivals happen between June and September. The Chicago Blues Festival, the world’s biggest free blues gathering, happens in June, followed immediately by the Chicago Pride Fest. July brings Taste of Chicago, where Chicago’s hottest restaurants staff outdoor booths and guests can sample from as many as 70 food vendors. August is all about music and Lollapalooza, and September’s events include the Renegade Craft Fair and Oktoberfest. The year ends with Christkindlmarket, a Christmas-shopping and German-food extravaganza, and the Magnificent Mile Lights Festival. If you're looking for something year-round, don't miss Second Fridays, the Chicago Arts District's monthly celebration of local creativity that takes place in Pilsen, one of the city's most culturally rich neighborhoods.
    Photo by Chuck Eckert/age fotostock
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    Chicago’s Classy Cocktails
    Chicago’s Classy Cocktails
    Chicago bartenders are as accomplished as the city's chefs, and visitors can drink creative and legendary cocktails all over the city. Scofflaw in Logan Square puts a spotlight on gin, and boasts a bigger selection of the spirit than anywhere else in town. If it's even more variety you're after, head straight to Milk Room, where spirits savant Paul McGee curates an ever-evolving list of vintage and rare bottles, maybe a Benedictine from the 1950s or a 1970s Fernet (with price points to match). Those looking for sippers a little less serious can check out Broken Shaker, a lobby-level drinking den in the Freehand Hotel that specializes in quirky riffs on classics cocktails.
    Photo by Adrian Gaut
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    Retail Therapy
    Retail Therapy
    Michigan Avenue’s Magnificent Mile boasts 460 retail stores, including those of high-end designers like Gucci, Cartier, and Louis Vuitton. Visitors come to Chicago simply to explore this rich retail bonanza, and many of them stay at the opulent hotels in the area (the Park Hyatt and the Peninsula, to name a couple) just to be near them. On the other end of the spectrum, plenty of treasures can be uncovered by thrift shopping for vintage housewares, accessories, and clothes at Una Mae's and Store B Vintage in Wicker Park. For bespoke and affordable gifts for any occasion, check out Havlan & West in Bucktown, where owner Emily McKenney curates a well-stocked inventory of apparel, jewelry, artwork, and home goods from local and international designers alike.
    Photo by Franz Marc Frei/age fotostock
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    Millennium Park and the Bean
    Millennium Park and the Bean
    Millennium Park covers 24.5 acres of Lake Michigan shoreline in the downtown Loop. Visitors here can listen to free concerts at the Jay Pritzker Pavilion, ice-skate on the rink, attend lectures and classes at the Lurie Garden, and admire the changing pictures of Crown Fountain. The stainless steel sculpture named Cloud Gate, otherwise known as the Bean, provides the best photo opportunity in the city; with careful framing, the entire Chicago skyline can be captured in a picture of this icon. Millennium Park is big enough to feel like you've escaped the urban bustle and small enough to enjoy in a single day.
    Photo by Franz Marc Frei/age fotostock
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    Theater, Comedy, and Improv
    Theater, Comedy, and Improv
    Chicago has a wonderful performing-arts scene, ranging from intimate storefront groups to touring Broadway shows and the famous improv comedians at the Second City. Cadillac Palace Theatre, Oriental Theatre, and Chicago Theatre in the Loop all have beautiful, richly decorated houses for large, extravagant Broadway productions. Goodman Theatre and Steppenwolf continue to break new ground with beautifully designed world premieres such as War Paint starring Patti LuPone. For spectacles in another area of the city, travel to Court Theatre in Hyde Park, where the team focuses on five shows every season that range from revived masterpieces to modern classics.
    Photo by Kim Karpeles/age fotostock
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    Flourishing Coffee Culture
    Flourishing Coffee Culture
    Chicago has a flourishing coffee culture led by Intelligentsia Coffee and Metropolis Coffee Company, both of which source coffee beans all over the world and do their own small-batch roasting. Dark Matter in Ukraine Village and Dollop in Buena Park are also worth a visit. All of these cafés pride themselves on fair-trade coffee practices and baristas who take their latte duties seriously, turning out consistently well-crafted espresso drinks. For delicious baked goods along with that cup of joe, visit Lovely Kitchen & Café on North Milwaukee.
    Photo courtesy of Intelligentsia Coffee
  • 8 / 10
    Chicago’s Wealth of Museums
    Chicago’s Wealth of Museums
    Chicago has a wealth of art museums, ranging in size from the tiny Ukrainian National Museum in Ukraine Village to large, formal museums like the Art Institute, whose European painting and sculpture wing has one of the world's most extensive assemblages of Impressionist-style paintings. History buffs will dig the Field Museum, one of the largest natural-history museums in the world, while space fanatics will be far better served at the Adler Planetarium, a museum founded in 1930 that is dedicated to all things astronomy and astrophysics. For a culture trip, try visiting the DuSable Museum of African American History on East 56th Place; for a celebration of Mexican culture, check out the National Museum of Mexican Art on West 19th Street.
    Photo by Franz Marc Frei/age fotostock
  • 9 / 10
    The Historic Ballpark
    The Historic Ballpark
    Wrigley Field was built in 1914 and maintains its rank as the second-oldest ballpark in the majors, right behind Boston's Fenway Park. The Chicago Cubs have been playing on it since 1916, and Chicagoans are fierce Cubs fans—especially now that they are world champions again (for the first time since 1908). Visitors can tour the field and take a picture with the commemorative statue of beloved sports commentator Harry Caray, which resides at the corner of Waveland and Sheffield. Other legendary Chicago sports teams the Blackhawks (hockey) and Bulls (basketball) play in the United Center; Michael Jordan, also one of Chicago’s favorite sons, is immortalized in his famous jumping pose right outside that venue's Gate 4.
    Photo by Larry Malvin/age fotostock
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    Blues and Jazz in the Windy City
    Blues and Jazz in the Windy City
    Open and thriving since 1907, the Green Mill Cocktail Lounge on Broadway survived ownership by one of Al Capone's henchmen in the 1920s and is still decorated like a Prohibition-era speakeasy. Go to the Green Mill for live jazz seven nights a week; after-hours shows play between midnight and 5:00 a.m. on Saturdays. For the three B’s—barbecue, beer, and blues—head to Lincoln Park. Spacious Kingston Mines can accommodate a big crowd, whereas the intimate B.L.U.E.S. is better appreciated in a small group. Both clubs are on North Halsted Street and have live music until 3:00 a.m. or later most nights of the week.
    Photo by Heeb Christian/age fotostock