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Arts and Entertainment in Chicago, Illinois, Milwaukee, Wisconsin Dells, Madison

Things to do / Travel Guide

Chicago and southern Wisconsin just has so much to offer in the way of entertainment! Chicago is legendary for having launching the careers of people like James Belushi, Mike Myers, Benny Goodman, and today's queen of television, Oprah Winfrey. Oprah once said of Chicago, “I set foot in this city, and just walking down the street, it was like roots, like the motherland. I knew I belonged here.” Everyone belongs in Chicago, and most of the entertainment from Chicago to southern Wisconsin stems from the immigrants that once walked the streets of the city. Jazz, improv comedy, opera, good old rock n' roll, and more, have all sprouted from and flourished on these streets.

No matter what section of Chicago you are in, you are never far from action. On the one hand, there are a few areas within Chicago known for entertainment, while on the other, the city's entertainment is spread out amongst its various communities.

The Loop being the historical, financial, and cultural center of Chicago, it's no surprise that a large amount of entertainment opportunities, particularly for the theater, are to be found there. The Loop is to New York's Broadway as off-Loop is to off-Broadway. The area's most well-known theaters include the Cadillac Palace Theatre, Ford Center for the Performing Arts Oriental Theatre (or just plain Oriental Theater), the Auditorium Theatre, and the Chicago Theatre; the theater district is located northwest of East Adams Street and North LaSalle Street.

One of the city's greatest entertainment districts is Uptown's. The Uptown Entertainment District has it all: clubs, theater, live music, restaurants, and pubs.
The action centers around Broadway, where you'll find the Aragorn, a music venue that's seen the likes of everyone from Frank Sinatra to Snoop Dogg to Grateful Dead; the Green Mill Jazz Club, formerly owned by an accomplice of Al Capone, and which regularly shows great jazz acts and weekly poetry slams; Uptown Theater, the largest movie theater in the city with over 4,000 seats; and others.

Fine Arts in Chicago

The Lyric Opera of Chicago, stationed in the middle of the Loop, helped launch the American career of Maria Callas in 1954. Known as one of the leading opera companies in the United States, it also seats almost 4,000 people - making it the second largest opera auditorium in North America. The Chicago Symphony Orchestra, near the Loop's Theater District, is a staple of the Chicago Classical music scene. While the season typically runs from September to May, they sometimes hold summer performances at the Ravinia summer festival.

Off-Loop Theater

With a little help from then-future “Friends” star David Schwimmer, the Looking Glass Theatre was established in the late 80s. The theater combines dance, improvisational theater, music, and circus arts, and is located in the Water Tower Works Building in Near North Side.

Other Off-Loop theaters are Steppenwolf Theatre, the Victory Gardens Theatre, and the Royal George Theatre Center; these are located either in Near North Side or Lincoln Park. Steppenwolf Theatre in particular is first-class, as it has launched the successful careers of actors such as John Malkovitch, Joan Allen, Gary Cole, and others, and several of the plays originating on its stage went on to win Tony's on Broadway.

Improv Comedy in Chicago

If music is the social lubricant of Chicago, then comedy is the fuel. The Second City has launched the careers of Tina Fey, Bill Murray, Dan Aykroyd, and John Belushi, among others. At Second City, the show is a mixture of polished act and improvisation, in which the comedy troupe works with the suggestions raised by the audience. Today, the Second City phenomenon has spawned other troupes in cities across North America and several improv schools - but it all started here, Chicago. The Second City is located in Old Town, a neighborhood in Near North Side.

The iO Theater, formerly known as the Improv Olymics, specializes in “long-form” improv, in which improv is treated as an art form in itself. The house favorite? the “harold,” which is based on one single audience suggestion, and has been compared to a masterpiece of the jazz variety. iO has been home at one point or another to Andy Dick, Mike Myers, Tim Meadows, Vince Vaughn, Chris Farley, and others. There are two locations in Chicago: the Cabaret, and the Del Close Theater, both next to Wrigley Field on North Clark Street.

Nightlife in Chicago

You will find bustling nightlife in many of the city's communities, but especially in the Loop, Uptown, Lakeview, Lincoln Park, Near North Side and the Gold Coast, and Near West Side's Wicker Park.

The club scene in Chicago is gaining notoriety with places like the Loop's Excalibur, which has three levels consisting of mainstream house music, hip-hop, and 80's beats; and Lincoln Park's Smart Bar, which has great DJ's for house and trance music, without the big bar attitude. Schubas, also in Lincoln Park, is the true place to hear tomorrow's musicians today. While the bar area is fun, it's also loud. Back in the music room, hardcore music fans will shush you if you dare speak!

Who can forget the House of Blues? In this music house where anything goes you won't see much blues, just lots of good, hard rock - and the occasional reggae or hip-hop act. High-profile bands have been known to play here, but it's a great chance to see up and comers also. Get there early though, because the place becomes a mob scene by show time. This is the country's largest House of Blues halls, located in the Loop.

One last premier club, to single out aside from the myriad others you're bound to enjoy in the Windy City: the Metro, located yet again in Lincoln Square. If Excalibur is for house, and House of Blues is for 80s-style hard rock, then the Metro is for the newest alternative acts: All at early points in their career, Nirvana, Pearl Jam, and Chicago's own Smashing Pumpkins were featured here.

Jazz and Blues

Al Capone had a favorite jazz spot, the Green Mill Cocktail Lounge. The lounge, located in Lincoln Square on Broadway, still manages to book top acts, just as it did 70 years ago. You'll feel like you just stepped into the 1930s - and you won't want to leave. For a better view of local jazz talent, head to Rosa's Lounge, in Logan Square.

Blue Chicago, and younger-sibling Blue Chicago on Clark, are both in Lincoln Square on Clark Street. Blue Chicago, a Chicago Blues institution, had been elsewhere when number two opened up, but then the former relocated to its present Clark Street location. Both specialize in the excellent local talent of Blues performers, with a lot of women performers; the younger is much smaller than the older, with the audience sitting almost on top of the musicians.

Another Lincoln Square mainstay is Kingston Mines, which boasts two audience-friendly stages. The stages often feature rivaling musicians, which promises always to keep the music hot. The music house is much more social than others, as the music never reaches the decibel level that would drown out conversation, and the halls are lit brighter than usually expected for such venues.

One last treat for all lovers of Chicago blues. If you ask, they might even play “Sweet Home Chicago” - at Rosa's Lounge, in Palmer Square. Acclaimed as one of the best haunts to hear blues in the city, the hall is intimate and decorated with highly-artistic graffiti and vintage photos on the walls. Local talent plus world talent perform at the lounge, and you'll meet plenty of locals in the audience, as well as aficionados from all over the country.

Fine Arts in southern Wisconsin

Wisconsin is not just known for its cheese and beer. Nevertheless, where you'll find beer, generally you'll find some form of entertainment,. The Milwaukee Symphony Orchestra has been dubbed by the New Yorker magazine a “virtuoso,” and its season runs from September through July. It's located right off North Broadway. Rated as one of the top ballet companies in the United States, the Milwaukee Ballet is a must see. Find it south of the Milwaukee River, on South 5th Street.

The Pabst Theater in Milwaukee on East Wells Street, has been showcasing modern singers, dance troupes, and comedians for over a century. Nearby, the internationally known Milwaukee Repertory Theater displays everything from classical performances, to contemporary shows, and cabaret. In Madison, the Broom Street Theater on the isthmus is home to experimental theater, and is not afraid to tackle touchy subjects in an entertaining way. The Barrymore Theater, on the northern neck of the isthmus, is a restored old vaudeville hall that showcases every big name act in comedy and theater, plus they host various film festivals.

Nightlife in southern Wisconsin

Jazz and blues are found bountifully throughout southern Wisconsin, thanks to the Great Migration of African Americans in the early part of the 20th century. If you're serious about the art form, head to Jazz Oasis in Milwaukee, just north of East North Avenue, especially for the open jam sessions. If rhythm and blues is your thing, then the Up and Under Pub is your stop. With the best of local and national blues bands, this is like taking a step back in time- to when music really rocked! You'll find the pub across the street from Veterans Park on East Brady Street, a stretch of trendy restaurants and pubs, in buildings hailing from the 1860s to the 1930s. For those that like to shake their groove thing, Have a Nice Day Café is the retro spot to truly stay groovy, located on the western side of the Riverwalk.

Free live jazz is offered every summer Thursday night from 6:30 to 9:00 at Cathedral Square Park, a few blocks from the lakefront. You're encouraged to picnic on the lawn, and food and drinks are sold in the immediate area.

You'll find that Madison has a vibrant college scene in addition to nightlife opportunities for the more mature fun-loving set. You'll find the college set concentrated around University Avenue and State Street, while other upscale locations are closer to the isthmus, in the Capitol Square area, and slightly more to the south. For an example, Luther's Blues, on University Avenue, is your place for roots rock and smooth blues, while Opus Lounge, in Capitol Square, has become a haven for those seeking great cocktails. The Lounge a little pricey, but worth it for one of the city's best martini!