If you’ve never been to Chicago, you may only equate it to Oprah, the Cubs and windy and cold winters. Dig a bit deeper and you’ll realize this influential city offers locals and visitors alike some of the nation’s best jazz clubs and improvisation troupes, world class shopping, restaurants, an amazing skyline and phenomenal architecture.
From the massacre at Fort Dearborn in 1812 to the famous gangsters of the Prohibition, Chicago is a city steeped in history—and not all of it is savory. Every neighborhood has its scary stories and sordid histories, and there’s no better time to explore the seamier side of Chicago’s past than on a blustery fall day as Halloween approaches. Wear something warm, bring a camera and someone’s hand to hold, and spend an evening finding out just how scary the Second City is.
Chicago is home to the blues, offering a lively scene with many blues clubs and bars scattered throughout the city. Get ready for a night devoted to the blue chord progressions and blue notes that make up this music genre while visiting Buddy Guy’s Legends, on Wabash Avenue in the South Loop, for a full evening of food, drink and blues.
The blues, contrary to its name, is a joyful, celebratory music, and the true blues experience occurs when there is a call and response from the instruments and the vocals, with an additional call and response between the audience and the band.
Despite its rough and ready reputation as "hog butcher to the world", Chicago is a city of great cultural wealth. This day of exploration discovers a portion of that wealth, much of it lodged in the city’s exceptional museums. Along the way we will visit another source of cultural wealth – the city’s diverse and colorful neighborhoods.
Cliché as it may seem, "dinner and dessert," can mean a blessed merriment for your taste buds. For a low key night out in Chicago, one merely needs to begin with a cheerful appetite, a little cash, and maybe some elastic waist pants, (no calorie counting on this trip). On this evening in Chicago, we start and end our night on West Randolph.
Chicago offers many solutions for those in need of a comedic fix. With outstanding comedy options like the Improv Olympics, showcasing long form improvisation shows, to the Annoyance Theatre where one can find innovative and often comical shows. Chicago’s rising stand-up comedians can be seen at the Lincoln Lodge, a restaurant with top notch stand-up comedy on Friday and Saturday nights or Chicago Underground Comedy, a stand-up comedy showcase on Tuesday nights at The Beat Kitchen. But it is another group that has put Chicago on the comedy map: The Second City.
When the weather is good for outdoor browsing, what better place to spend the day than on Chicago’s trendy West Division Street? With a hip strip of boutiques and trendy eateries, this area known as Bucktown is becoming quite a popular hangout. Even moms with strollers are in tow are among the crowd.