Chicago City and Culture

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Chicago City and Culture
Visit Chicago for action-packed days full of sensational sports games, cocktails and shopping on the Magnificent Mile, and cruises on the Chicago River, followed by live blues concerts and hilarious comedy shows.
By Kaitlyn Barrett, AFAR Local Expert
Photo by Heeb Christian/age fotostock
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    Blues and Jazz in the Windy City
    Open and thriving since 1907, Green Mill Cocktail Lounge on Broadway survived ownership by Al Capone in the 1920s and is still decorated like a Prohibition-era speakeasy. Go to Green Mill for live jazz music 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 Halsted Street and have live blues jams until 3:00 a.m. or later most nights of the week.
    Photo by Heeb Christian/age fotostock
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    Chicago Architecture
    Many famous architects contributed to Chicago’s skyline, most notably Louis Sullivan with his elegant neoclassical structures and Mies van der Rohe with sleek black-and-glass skyscrapers. Other remarkable buildings include 96-story Trump Tower, 108-story Willis Tower—which was the tallest building in the world until 2010—and Marina City’s circular “corncobs.” All of these beauties and many more are best appreciated from an architecture cruise along the Chicago River or from the 103rd floor Skydeck of Willis Tower. The Chicagoland area also has the nation’s largest concentration of houses designed 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
    Chicago’s best outdoor festivals happen between June and September. Chicago Blues Festival, the world’s biggest free blues festival, happens in June, followed immediately by the Chicago Pride Fest. July brings Taste of Chicago, where Chicago’s hottest restaurants staff outdoor booths and visitors can sample from more than 70 food vendors. August is all about music and Lollapalooza, and September’s festivals include the Renegade Craft Fair and Oktoberfest. The year ends with Christkindlmarket, a Christmas shopping and German food market that’s part of the Magnificent Mile Lights Festival. Chicagoans also celebrate a number of local ethnic festivals, neighborhood parties, and holiday events throughout the year.
    Photo by Chuck Eckert/age fotostock
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    Chicago’s Classy Cocktails
    Chicago bartenders are as accomplished as the city's chefs, and visitors can drink creative and classic cocktails all over the city. Scofflaw in Logan Square specializes in gin, and boasts a bigger selection of the spirit than anywhere else in the city. There's everything from small-batch brands to their own house brand, Old Tom gin. For an awe-inspiring whiskey selection, go to The Grafton on Lincoln Avenue and order a burger, chased with the whiskey of your choice. The Violet Hour in Wicker Park is the sexiest, swankiest speakeasy in town, and no visitor to Chicago should leave without having a cocktail at The Signature Lounge on the 96th floor of the John Hancock Building, with its epic views.
    Photo by John Joh
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    Rich Retail Therapy
    Michigan Avenue’s Magnificent Mile boasts 460 retail stores, including 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 near these fabulous stores. On the other end of the spectrum, plenty of treasures can be uncovered by thrift shopping for vintage vinyl and clothes at Reckless Records and store B vintage in Wicker Park. Hollywood Mirror on Belmont has a vast array of colorful Halloween costumes, Japanese dolls, and tacky, tawdry toys, while Old Town offers artisan pleasures like hand-ground spices at The Spice House and handmade stationery at Pulp and Ink.
    Photo by Franz Marc Frei/age fotostock
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    Millennium Park and The Bean
    Millennium Park covers 24.5 acres of Lake Michigan shoreline in the downtown Loop. Visitors can listen to free concerts at the Jay Pritzker Pavilion, ice-skate on the rink, attend lectures and classes at Lurie Gardens, see the magnificent Buckingham Fountain spray water on the edges of Lake Michigan, and admire the changing pictures of Crown Fountain. The stainless steel sculpture known as The Bean provides the best photo opportunity in the city, and with careful framing, the entire Chicago skyline can be photographed as well. Millennium Park is big enough to feel like you've escaped 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
    Chicago has a wonderful theater scene, ranging from intimate storefront groups to 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 the upcoming musical War Paint starring Patti LuPone. The Neo-Futurists up north on Ashland put on 30 shows in 60 minutes (and charge the price of a dice roll for admission), and for those visitors with no extra dollars to spare, Second City hosts a free improv show on Friday nights called The Midnight Melt.
    Photo by Kim Karpeles/age fotostock
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    Flourishing Coffee Culture
    Chicago has a flourishing coffee culture led by Intelligensia 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, as is La Colombe in Wicker Park, under the L tracks. All of these cafés pride themselves on fair trade coffee practices, freshly roasted beans, 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 Bake Shop, which has branches in Lincoln Park and Andersonville.
    Photo courtesy of Intelligentsia Coffee
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    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 the most Impressionist-style paintings outside of the Musee D’Orsay in Paris. For more recent, multimedia work, there's the Museum of Contemporary Art with its permanent collection of 2,500 objects from 1945 to the present, including a strong representation of local artists. For an in-depth view of African-American history and art, visit DuSable Museum of African American History on East 56th Place, and for a museum celebrating Mexican culture, visit the National Museum of Mexican Art on West 19th Street.
    Photo by Franz Marc Frei/age fotostock
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    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 Wrigley Field since 1916 and Chicagoans are fierce Cubs fans, even when their team loses. Visitors can tour historic Wrigley Field and take a picture with the commemorative statue of beloved sports commentator Harry Caray, which is right outside the field. Chicago’s other famous sports teams, the Blackhawks (hockey) and Chicago Bulls (basketball), play in United Center. Michael Jordan, another of Chicago’s favorite sons, is immortalized in his "JumpMan" pose right outside the venue's Gate 4.
    Photo by Larry Malvin/age fotostock